Where to Stay in Chicago - A Local's Neighborhood Guide
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As a lifelong Chicagoan, I like to think I know my city pretty well. But then again, it still has the capacity to surprise me. And that’s the great thing about living in such a dynamic cultural and regional powerhouse: there’s always something new to explore in this wonderfully diverse city of 77 distinct neighborhoods.
In fact, in addition to its more famous moniker “The Windy City” (a name that derives more from its less-than-truthful old-time politicians than its windy Midwest climate), Chicago is also sometimes referred to as “The City of Neighborhoods.” And while it’s true that most first-time visitors fail to venture outside of the city’s tourist core, I would encourage you to carve out some time to explore the “real Chicago” beyond the downtown district.
That being said, downtown is still the obvious choice and my usual recommendation for any Chicago newbie. It offers a world-class combination of architecture, arts, beaches, business, and culture all tucked right along the windswept shores of Lake Michigan.
While I think downtown is ideal for most people, I’ve also included a number of less central, but more local neighborhoods that could be good choices either for returning visitors, anyone on a longer trip, or people who just want to get a feel for local Chicago.
Table of Contents
Overview of Chicago's layout
Unlike some of America’s older colonial-era cities, modern Chicago is neatly laid out on a grid, as a result of much of downtown being burned and rebuilt following the Great Chicago Fire of 1871. Lake Michigan is always to the east (helpful to know if you get lost), with stronger lake breezes and often slightly cooler temperatures downtown as a result.
Know that within the city center the nomenclature of the neighborhoods can be a bit confusing: The Loop is Chicago’s core and what most people refer to when they say “downtown,” but downtown can also include the neighborhoods surrounding the Loop such as River North, West Loop, and South Loop.
Whether you confine it to just the loop or add in the surrounding neighborhoods, the entire downtown area is extremely walkable. This is especially true from spring through fall, but during the winter you’ll probably want to explore by car as the cold is intense - trust me.
Chicago’s subway (known as the “L”) is also quite reliable and connects most downtown attractions, while Ubers and taxis are plentiful for exploration further out into other parts of the city.
Keeping the Loop as our central reference point, the other neighborhoods that I’ve recommended below are either a bit farther north or west. They’re less convenient to the main sights and are a little bit less walkable (although you can still totally get around on foot), but are much more residential and local, giving you a nice look into everyday life here.
Summary of my 7 recommended neighborhoods
Before talking about the different neighborhoods I recommend, I want to add a quick note on why I've listed 2 neighborhoods together in many cases. I've done this for neighborhoods that are geographically adjacent to each other and pretty similar in character. This doesn't mean that staying in them will give the exact same experience, but it'll be pretty similar.
For example, Streeterville and Gold Coast are separate neighborhoods, but their borders blend and the vibe is quite similar. One is a little more downtown-y, but if you were just walking around you wouldn't really notice where one neighborhood ends and the next begins.
This is true for places like Wicker Park and Logan Square too. They're next to each other, both a bit "hipster” and gentrifying, and a little more gritty than the wealthy downtown neighborhoods. Although they're distinct from each other, you'll get a pretty similar experience in both.
1. The Loop (red on the map above)
Chicago's downtown, this area is home to many of the city's main tourist attractions and is a major transport hub. It's rightfully home base for most first-time visitors. Here, you'll find the Art Institute of Chicago, the Skydeck observation tower, Millennium Park (home of the uniquely shaped “Bean” sculpture/tourist trap) and the lake-adjacent Grant Park (home to Lollapalooza music festival every summer). Like most business downtown's, it's not the most atmospheric of areas, but if you're here for just a couple of days and want to stay central and as close to the sights as possible, it's a good choice.
2. River North & Mag Mile (purple above)
This is the area immediately north of and across the Chicago River from downtown. The World-famous Magnificent Mile (Michigan Avenue) is here, and all along it you have a ridiculous abundance of iconic architecture, endless shopping opportunities, loads of cafes and restaurants, and boisterous bars and clubs. It's fairly similar to the Loop (with most of the same positives), but slightly more residential and with better shopping and dining. It's a major nightlife area, so great for younger travelers or anyone planning on hitting the town, but not necessarily the best choice for older travelers or anyone looking for peace and quiet.
3. Lincoln Park & Lakeview (yellow above)
You really start to get a local neighborhood feel as you move away from the city center and into Lincoln Park and Lakeview, two wealthy, but laid back areas north of downtown. Popular attractions include the free Lincoln Park Zoo, Wrigley Field (home of the Cubs) and the expansive North Avenue Beach, which bursts to life in the summer with beach volleyball and cocktails on the water. I think it's a great area for families with kids and travelers over the age of 30 who are looking for a city base that offers a relaxed, neighborhood vibe.
4. Streeterville & Gold Coast (green above)
These two neighborhoods that lie along the shores of Lake Michigan are north and east of River North and the Magnificent Mile. They're wealthy areas that have a mix of downtown and residential vibes. Some streets are leafy and lined with townhouses while others have high-rise luxury condos and there are loads of high-end dining options. Aside from good beaches, a few of Chicago’s most visited attractions, including the 360 Chicago observation deck and Navy Pier, are also here. It's expensive and a little bit pretentious, and the crowd definitely skews older, but it's solid choice for luxury travelers and anyone who wants to stay very close to downtown, but with an elegant and more residential atmosphere.
5. West Loop & Fulton Market (blue above)
West of the Chicago River, the West Loop/Fulton Market area feels very distinct from its downtown cousins. Slightly less touristy, with lower buildings, and less of a business-oriented atmosphere, this is a major dining and nightlife district made up of renovated and repurposed brick warehouses. Some of the city's finest high-end restaurants are located along “Restaurant Row” (Randolph Street) and the area is also home to some of Chicago’s newest boutique hotels. It's a bit of a "sleeper pick”, but worth considering for travelers in their 30s, 40s, and 50s, especially those who are interested in the city's dining scene. It's also one of the few neighborhoods in/around downtown where you'll actually be able to park a park.
6. Wicker Park & Logan Square (dark purple/magenta above)
If you find yourself “too cool” for each of the aforementioned more “mainstream” neighborhoods, the Wicker Park and Logan Square neighborhoods located northwest of the downtown are top choices for anyone after offbeat arts, divey music clubs, cool cocktail bars, and trendy restaurants, especially along the “Hipster Highway” of Milwaukee Avenue. It's further from downtown (you'll need to take the subway/bus), but these are the types of neighborhoods that locals come to for eating, drinking, and hanging out, so great if that's the scene you're after.
7. South Loop & McCormick Place (black/grey above)
While similar to its neighbor to the north (the Loop), the South Loop has more of a middle class vibe and is home to some of Chicago’s biggest lakefront attractions including Soldier Field (home of the Bears), the Field Museum, and the Adler Planetarium. Further south, McCormick Place is a popular district for large meetings and conventions - and is full of big hotels as a result - but it can feel a bit empty and soulless. I like the part of the South Loop that's closer to downtown and the museums, especially for people traveling with kids as access to Grant Park and green spaces is very good.
1. The Loop
Best for: First-time visitors seeking a central location for sightseeing
Pros: High concentration of top attractions in a compact area, great hotel selection, walkable, good public transport
Cons: Can be quite touristy and crowded, very downtown feel
A boat passing under DuSable bridge, with the Loop's skyscrapers on the right
When most people think of Chicago, they picture the Loop: home of towering skyscrapers jutting up against Lake Michigan and running all along the Chicago River in a gorgeous juxtaposition of our natural and human-made worlds. This is Chicago's business downtown and also a national hub of urban culture and commerce.
Unusually for a downtown, the Loop also showcases some of the city’s natural jewels: Lake Michigan and its waterfront (including Grant Park and Millennium Park) and the Riverwalk. The lakefront has year-round action, with the added bonus of live music in the summer months.
The neighborhood derives its name from the iconic subway cars that rumble on elevated tracks overhead, making a literal loop around the downtown. The name alone lets you know that the area is extremely well-serviced by public transport with trains and buses connecting it to almost every neighborhood in the city.
In terms of atmosphere, it's what you'd expect for a business district; walking down the street, you'll see a mix of mostly commercial buildings housing corporations, government offices, universities, financial institutions, and the types of bars/restaurants that cater to workers. It doesn't have the frenetic energy of somewhere like New York, but it's very much a busy and active downtown.
While this is a bustling commercial area during the day, few people actually live here and it can become much more quiet after night falls and workers head back to the more residential neighborhoods in which they live. Downtown feels more rushed and goal-focused during the day, but things tend to relax a bit in the afternoons as street performers entertain tourists and lunch crowds linger on sidewalks before heading back to the office. Early evenings are always busy with people grabbing happy hour drinks.
Even as a local, I often visit the area for work-related tasks and errands, and I also like to come every now and then to just wander around without a plan, taking in the gorgeous skyscraper views, relaxing in the park, or walking along the lakefront.
Full disclosure, the area can be quite touristy and it gets really congested during popular events like Lollapalooza or the St. Patrick’s Day Parade. It also doesn't feel "lived in” or particularly local, so won't be a great fit if that's that what you're looking for. I find staying in downtown areas of many cities to feel a bit soulless, but I don't think that's the case for Chicago.
Aside from being extremely convenient from a logistics standpoint, there's also genuinely a lot to do. Many of Chicago's star attractions and premier cultural centers are also here. A couple blocks inland from the lake, you have the wonderful the Art of Institute of Chicago, there's also the landmark Chicago Theatre (one of the midwest's best venues for live music), and a stroll along the Chicago Riverwalk will give you a great sense for the feel of the city as you watch boats glide along the water surrounded by gleaming skyscrapers.
For dining, you have lots of options, from quick-service restaurants catering to the working crowd to quite upscale spots for post-work dinner and drinks. In terms of accommodation, you have a huge selection of hotels, though there are few budget options.
In general, I recommend the Loop to most people coming to Chicago for the first time and especially anyone who prioritizes staying central and close to the major sights. If you're looking for a more residential area, somewhere hip and cool, or just a more authentic taste of what it’s actually like to live in Chicago, you should probably look at some of the neighborhoods further down this list.
Where to stay
Chicago Athletic Association - This historic 4-star hotel was once, as the name suggests, home to a local athletic association. Today, it's what I like to call "nice but not too fancy” and it has an absolutely unbeatable location on Michigan Avenue across from Millenium Park. The best part about staying here, though, are the half-dozen cool bars and restaurants you’ll find within the building, from the barroom-style Game Room to the 13th-floor Cindy’s Rooftop Bar – unfurling easily the best view in the city. $300 USD per night.
Pendry Chicago - Opened last year (2024) to much fanfare and inside one of Chicago’s most historically significant buildings, the vibe here is sleek and stylish with gorgeous common areas, one of the best rooftop bars in the city, and large rooms that are luxurious, but understated. The location is great too, right along Michigan Avenue in between Millennium Park and the Chicago River. $300 USD per night.
LondonHouse - Another historic gem famous for its rooftop bar (which overlooks the Chicago River and downtown architecture), the rooms here are elegant yet simple, and the hotel also offers spa treatments for those seeking a bit of extra pampering. The bar is a popular spot for summer daytime drinks and evening dancing. $200-300 USD per night.
Virgin Hotel Chicago - A touch of British elegance greets visitors to this lively downtown hotel. Rooms feature fun and unique touches like vintage mini-fridges and exterior doorbells. $200-300 USD per night.
Cambria Hotel Theatre District - If seeing an opera or a play in Chicago’s theatre district is on your agenda, this more affordable 3-star choice offers a stellar location next to the Nederlander Theatre and basic yet comfy rooms. If staying here, be sure to hit up the 14th floor for a night of unique dinner theatre you’ll never forget at the Cirque du Soleil-styled Teatro ZinZanni. $160-225 USD per night.
River Hotel - This is always my recommendation for anyone traveling on a budget, but who wants to stay right downtown. The rooms are small and simple, but they're clean and comfortable, and the location - just half a block from both Michigan Ave and the Riverwalk - is great. $150-200 USD.
citizenM Downtown - citizenM is an international hotel group that offers budget hotels that hit all the basics with a little bit of style. The Chicago offering has rooms that are small, but new, well appointed, and thoughtfully designed. The location is good too. $130-200 USD.
2. River North & Mag Mile
Best for: People looking for proximity to downtown and the sights, but also with good nightlife and shopping
Pros: Lively entertainment and shopping district that keeps the party going late, always bustling
Cons: Pretty touristy, commercial vibe
Looking through River North and towards Lake Michigan from along Chicago Avenue. Photo: w_lemay, CC BY-SA 2.0, via Wikimedia Commons
River North is the first neighborhood north of the Loop, directly across the Chicago River from it. It feels quite similar to the downtown with big skyscrapers, wide streets, and a fairly commercial atmosphere, but it's different in that people actually live here and it has residential areas.
The main attraction of the area is Michigan Avenue's fabled Magnificent Mile (or Mag Mile), home to some of Chicago's most high-end stores and luxury fashion boutiques. It's also a major dining and nightlife district and where most visitors get their first taste of Chicago's raucous party scene. But there's more to do than just shop, eat, and drink.
Here, you’ll find some of the city’s most gorgeous architecture, especially in the Pioneer Court area immediately north of the Chicago River where historic gems like the Tribune Tower and Wrigley Building can be photographed in all their glory.
From art galleries and design showrooms to luxury apartments and high-end restaurants, River North is where much of the Loop crowds head to after work for drinks and dinner. I also actually come here fairly often at night to visit the bars, restaurants, and music clubs, and it's an area that I take visiting friends after a day sightseeing in downtown. You have lots of options for post-dinner activities, but for a unique after-dark experience, make sure to check out art projected onto the exterior façade of the world’s largest commercial building: THE MART.
Whether you want to bask in gorgeous views of the city from high-end rooftop bars at spots like LondonHouse or get down and dirty at local dive bar Rossi’s, there’s always something tempting you to stick around this area for “one more drink.” From modern club music at Celeste to old-school blues at Blue Chicago, there's lots to keep you entertained.
I recommend River North to travelers who want the convenience of being downtown, but with a slightly more residential atmosphere. It's also ideal for younger travelers or anyone planning on hitting the town and doing some partying. It’s probably not the best area for those traveling with families or folks looking for a quiet getaway, although pockets of nature and sandy beaches can still be found.
Where to stay
Intercontinental Chicago - This is a great option for anyone after an unbeatable Mag Mile location and luxurious accommodations that don't totally break the bank. It's a lovely hotel just steps from the Chicago Riverwalk and Pioneer Square. Rooms are luxurious, albeit a bit small, and you also get access to an ornate Olympic-sized swimming pool on the 14th floor. I regularly recommend the hotel to my own friends and family. $250-350 USD per night.
The Godfrey Hotel - This chic outpost is popular with locals and visitors alike due to its I|O Godfrey Roofscape, easily one of Chicago’s most gorgeous patios which operates year-round thanks to its retractable roof. Rooms are big and modern with a minimalist decor. The hotel’s on-site Mediterranean restaurant Yasemi is also actually quite good. $180-300 USD per night.
The Drake - One of Chicago’s most iconic structures (best viewed from Lake Shore Drive), many locals know this hotel because of their legendary New Year’s Eve parties which they've been throwing since 1920. It's a historic property and the rooms lean into that vibe with a bit of an old school vibe, but with nice updates. If you can get a lake-view room, even better. $150-250 USD per night.
Freehand Chicago - This hipster-approved upscale hostel (or “poshtel”) offers affordable stays at a great location, with a lively scene and fun vibe at its tiki-inspired cocktail lounge Broken Shaker. In addition to festive cocktails at one of Chicago’s best cocktail bars, Freehand offers your choice of rooms from shared hostel-style accommodations to private quarters. $100-200 USD per night.
3. Lincoln Park & Lakeview
Best for: Anyone who wants to stay somewhere that feels residential and local, travelers in town for baseball/sports, local bar culture
Pros: Close to downtown but unique and relaxed neighborhood feel, good dining and bar scene, gorgeous houses/brownstones, leafy
Cons: Very expensive, pretty yuppie (in Lincoln park), very few hotels. Lakeview can sometimes feel like one big sports bar
Apartments on Fullerton Ave, near to DePaul University in Lincoln Park. Photo: Pokemonprime, CC BY 4.0, via Wikimedia Commons
The South Pond in Lincoln Park's identically named Lincoln park. Photo: Alanscottwalker, CC BY-SA 3.0, via Wikimedia Commons. Cropped
A street in Boystown. Ken Lund from Reno, Nevada, USA, CC BY-SA 2.0, via Wikimedia Commons. Cropped
Wrigley Field in Wrigleyville with downtown Chicago in the distance. Photo: Sea Cow, CC BY-SA 4.0, via Wikimedia Commons. Cropped
These two neighborhoods, while adjacent to each other, are actually quite distinct. I've listed them together because they're both pleasant residential areas outside of downtown and they have similar appeals (although for slightly different age groups) and similar drawbacks. For the sake of helping you choose you might prefer, I've separated them below.
Lincoln Park
Lincoln Park (or LP for short) is a gorgeous, tree-lined neighborhood just north of downtown and Gold Coast that has long been one of Chicago’s most desirable residential locations. Named after the lovely and expansive park that runs along its eastern edge, here you get pleasant streets, beautiful architecture, and terrific access to green space and the lakefront.
The neighborhood is leafy and mostly made up of single family homes and 2 or 3-story townhouses (often occupied by a single family), providing a very different atmosphere to the soaring towers of downtown and the mid-rise condos of places like West Loop.
The main avenues are full of cool restaurants, cafes, shops, and bars, but the side streets quickly become residential. It's densely populated and extremely walkable, but still quiet.
Home to working class residents until the 1950s, the historic beauty and close proximity to downtown and the park made the area an early target for gentrification (before it was a household term) and it has seen decades of what former locals would call a “yuppie invasion”, which shows no signs of abating. There are lots of 30-something professionals here and a mix of young and long-established families. As such, the dining and nightlife scene, while quite good, is definitely on the more relaxed side.
The area is also home to DePaul University, and you’ll find lots of more student-oriented commerce immediately surrounding the campus.
Comparatively poor access to public transport make this a slightly inconvenient neighborhood for sightseeing, but you do have access to two subway lines and a number of buses that run straight into downtown. Regardless of whether you take a car, bus, or metro, consider that it'll probably take you 30-40 minutes to get to Millennium Park from most of the neighborhood.
If you're going to be using the subway a lot, you should look for a hotel close to the Fullerton metro stop (Red line - near DePaul University) or the Armitage stop (Brown line). I prefer the area around Armitage as it's more residential and less college-oriented, and the houses and architecture are absolutely gorgeous.
Although there are no major sights in LP, it’s a pleasant base for people who want to stay somewhere residential, fairly close to the sights, and with good dining and nightlife options. Families with young kids will probably find access to things like playgrounds and parks very appealing. Younger visitors might find the area a bit boring and I don’t think it makes sense for a quick sight-seeing focused trip, but if you’re coming for a repeat visit and looking to hang out, it’s a good choice.
Lakeview
Lakeview is a neighborhood just north of Lincoln Park that is a popular post-college party center. It's a big area, so has a few "micro neighborhoods” within it like Boystown (Chicago’s most well-known LGBTQ community) and the very fun neighborhood of Wrigleyville, home to Wrigley Field and the Chicago Cubs. If I'm being honest, catching a daytime baseball game at Wrigley Field will offer a better explanation of what Chicago is all about than any article I could ever write.
Lakeview is younger, more diverse, and less predominantly affluent than Lincoln Park. You get a wider range of people here and it’s markedly busier, especially in the evenings. You'll find lots of live music bars, a few concert venues, some theaters and comedy clubs, and the dining and nightlife is a bit more raucous and less refined than LP. Although you have plenty of fancy options, you also get a lot of burger joints, chicken wings, and sports bars with huge TVs. For visitors in their 20s or anyone looking to party, I think it’s a fun choice.
Lakeview has a number of metro stops in it, but it's a big area, so you may find yourself needing to walk 10-20 minutes to the nearest stop. Getting into downtown will take you 5-10 minutes longer than from Lincoln Park. Realistically, you'll probably find yourself calling an uber at least once or twice if you stay here. Although having to take (and pay) for uber/taxis is annoying, hotel prices are quite a bit cheaper here, so it does offset the cost.
I think the same people who like Lincoln Park will mostly also like Lakeview. That said, it's younger, a bit more "broey”, busier, more commercial, and less polished. In general, I think it's ideal for people in their 20s or older visitors who want to stay somewhere that's local and fun, but less buttoned up than Lincoln Park.
Where to stay
Hotel Zachary - If seeing a Cubs game at Wrigley Field is high on your Chicago to-do list – and it most certainly should be – there’s no better place to crash after a long day of eating, drinking, and cheering than this luxury offering from the billionaire Ricketts family (who also just so happen to own the Cubs.) It's literally across the street from the ballpark too! $400 USD per night.
Villa D’Citta - This luxury boutique mansion offers ornate, neighborhood B&B-style accommodations that you wouldn’t expect to find in the middle of America’s third-largest city. It's one of the most pleasant places to stay in Chicago and in a beautiful part of a beautiful neighborhood. You can thank me later. $250 USD per night.
Hotel Lincoln - This is one of Chicago’s most popular boutique hotels for a reason. Okay, a few reasons. Number one: its picturesque location across from Lincoln Park and Lake Michigan. Number two: its ever-popular rooftop bar/restaurant "J. Parker" (home to one of Chicago’s best burgers.) Number three: The price: Four stars for under $200. You can’t beat it. $180 USD per night.
4. Streeterville & Gold Coast
Best for: Older travelers, people looking for an upscale atmosphere, anyone wanting good access to the beach
Pros: Gorgeous lake-adjacent area home to gleaming beaches, museums, luxury high-rises, and elegant brownstones. Still close to downtown's sights
Cons: Can feel pretentious, quite expensive, home to the overcrowded tourist trap known as Navy Pier
Ohio Street Beach and high-rise hotels and condos in Streeterville
From steel and glass skyscrapers and luxury condominiums to historic mansions and designer boutiques, the neighborhood of Streeterville is made up of some of the finest real estate in Chicago. The scenic district extends from Michigan Avenue to Lake Michigan and is adjacent to the equally posh Gold Coast (derisively referred to by some locals as the “Viagra Triangle” due to the large presence of older single men frequenting some area clubs and restaurants.)
Regardless of what you call it (and what you think of it), there's no denying the fact that this is a beautiful area that every first-time visitor should see up close.
With a residential base made up of old-money retirees and wealthy middle-aged professionals, this area isn’t exactly “young and hip” and it lacks much of the frenetic energy of the rest of downtown. Yet, that may be a plus for those looking for a good location by the lake, but with a more relaxed atmosphere, tree-lined streets and, a more residential feel. Prices are not cheap, so expect to pay a premium for such prized tranquility.
While in the area, be sure to check out the insane observation deck at 360 Chicago for a bird's-eye view of the city and Lake Michigan and then take a stroll to my favorite beach, the lesser-known Ohio Street Beach, where skyscrapers rise just across from the sand along legendary Lake Shore Drive. In summer, congregations of boaters gather to party in the water just off the beach in an area of the lake known as the “Playpen”.
There are other great beaches too, like North Avenue Beach and Oak Street Beach, which is always full of people swimming and playing beach volleyball. When it's not beach weather (meaning most of the year in Chicago!), the Museum of Contemporary Art is another must-visit neighborhood attraction.
And, of course, there's the overrun lakeside playground known as Navy Pier. And sure, it’s worth seeing, but it's also the biggest tourist trap in the city. So, if you go, get a photo of the Ferris wheel, check out the massive yachts, and grab a drink at the world’s largest rooftop bar (Offshore Rooftiop). But please don’t mistake this for the “real” Chicago. It's tourist central, so know that, and then feel free to explore at your own risk.
When deciding which area to stay in, know that Gold Coast feels markedly more residential and “lived in” than Streeterville, which feels like what it is – basically still a part of the commercial downtown. While I find Gold Coast’s ambiance a little more pleasant, you have more hotels in Streeterville and it’s closer to the sights.
Where to stay
The Peninsula - Chicago has a lot of seriously luxurious hotels, but if you've got money to burn, the Peninsula might just be the best. Want a hot tub in your room? A rooftop skating rink in winter? Or how about a heated indoor pool that's so nice it borders on absurd? Don't even get me started on the rooms. Everything here is a delightful blend of Old World elegance and modern comfort. $600+ USD per night.
Viceroy Chicago - My favorite hotel in the city is this elegant yet understated 4-star gem in Gold Coast that offers one of the best combination lake/city views in the are. Said views are best enjoyed from Pandan, the hotel's sleek 18th-floor rooftop lounge that comes complete with a laid-back outdoor pool. A great choice for couples, I like this hotel so much that my wife and I stayed here on our wedding night. $300 USD per night.
Hotel EMC2 - Tired of the same old hotel rooms? I guarantee you’ve never stayed in a room like the ones at Hotel EMC2, a fun and unique concept inspired by Albert Einstein. Rooms include one-of-a-kind touches like large-scale gramophones and see-through showers in the middle of the room. The on-site Italian restaurant, The Albert, is just as inventive. It's another of my top recommendations in the city. $265 USD per night.
Sable at Navy Pier - Those dead-set on staying at Navy Pier could do much worse than this newish offering from Hilton’s Curio Collection. Downtown’s most easterly-oriented hotel offers unrivaled views of Lake Michigan that make you feel like you’re on your own private island after the tourist masses go home at night. Steps from the Ferris wheel and Offshore rooftop bar, there is simply no better view in Chicago. $265 USD per night.
Acme Hotel Company - This hipster-beloved spot is easily one of the coolest place to stay downtown, and this isn’t just because some of the rooms come outfitted with their own ESP guitars. Trendy art and murals adorn the space and it also plays host to one of Chicago’s top mixology bars, The Berkshire Room, in addition to its fun apres-ski inspired, hot hub-equipped private party room Bunny Slope. Yes, you read that right. Great for the young (and young at heart), I'd probably skip it if you're in town with your kids! $150-250 USD per night.
The Whitehall BW Premier - For a budget-ish option, this Best Western is tough to beat. The building is historic, the rooms are big and comfy, and the location is convenient for getting to Mag Mile, the lake, downtown, and up into pretty Gold Coast. It won't wow you, but it's a good deal. $130-200 per night.
5. West Loop & Fulton Market
Best for: Travelers who want to enjoy the city's trendiest restaurants and nightlife, anyone looking for boutique hotels
Pros: Close to downtown but feels like a real neighborhood, lively food and drink scene
Cons: Bit of a walk into downtown, few hotels
Randolph Street
This upscale neighborhood west of the Chicago River is most well-known for its “Restaurant Row” of highly acclaimed restaurants on and around its main strip of Randolph Street, but as the area keeps growing, so too does its gastro and nightlife appeal.
The area was once a major warehouse district and that architecture remains with lovely multi-story brick buildings. Though it was once gritty and industrial, the warehouses have been renovated and turned into expensive lofts, galleries, chic bars, restaurants, and corporate offices. Its humble origins exist on the outskirts, but the central core, especially around Fulton Market, is now very high end.
Corporations, like McDonald’s and Google, now actually have their regional headquarters here and a trio of high-end hotels have also set up shop; Nobu, the Hoxton, and Soho House. The area is extremely popular with wealthy young people, especially those working in tech.
For leisure, you can do things like catch a rooftop movie at the Emily Hotel, play Bocce ball on the outdoor patio at Kaiser Tiger, drink while playing video games at Emporium, or sip some of the fanciest cocktails in America at the Aviary.
This is also popular gathering place after Chicago Bulls and Blackhawks games at the nearby United Center. It can certainly feel pretentious in parts, particularly around some of the more high-end hotels and restaurants, but there are still plenty of more working-class corners to chat sports over a burger and beer.
During the summer, a number of popular Chicago festivals take place here, including Taste of Randolph and Pitchfork Music Festival, making it a good base if you're in town for one of those events.
Although a lot of people live here now, it’s mostly a dining and nightlife hub, so while there are plenty of people around during the day, there’s nothing particular to see/do and there are no traditional sights. It's a perfectly pleasant place to be, but you're more likely to find yourself in other parts of Chicago for sightseeing or daytime hanging out. Personally, I like to come here for the occasional nice dinner with friends or a romantic date night, but it's not somewhere I spend a lot of time hanging out in otherwise.
For transport, the area is easily accessible to and from Chicago’s downtown via the Green and Pink lines. From Fulton Market (at the Morgan stop), it's just a 15-minute metro ride to Millennium Park, and even fairly walkable to the Loop and downtown (around 30 minutes). That said, if you're thinking about staying here to get better prices than in downtown, forget it - hotels here now usually cost the same or more.
In general, I think that the West Loop is a good choice for visitors who want to stay close to Chicago's main attractions, are interested in upscale dining, and want a slightly more local vibe (albeit an upscale one) than you'll get in downtown. If you're looking for absolute proximity to sightseeing, easy park/lake access, or a down to earth local atmosphere, it wouldn't be my first choice.
Where to stay
Nobu Hotel Chicago - Sushi and 5-star splendor go hand-in-hand at this luxury hotel owned by Robert De Niro’s hospitality group. The celebrity appeal extends throughout the comprehensively breathtaking artist-inspired space, where you’ll discover large rooms and sick White Lotus-styled villas for the ultimate in Chicago opulence. $425 USD per night.
The Hoxton Chicago - One of the best places to see and be seen in the West Loop is this new-ish outpost offering British-inspired elegance and perhaps most well known for its always in-demand basement cocktail lounge, Lazy Bird. Uniquely appointed rooms offer more of an apartment-styled feel, while the Peruvian-inspired rooftop restaurant Cabra from local celebrity chef Stepfanie Izard remains equally as in-demand. $425 USD per night.
The Emily Hotel - Want to watch movies on a cool rooftop surrounded by fabled Chicago architecture? This Fulton Market space made its name hosting the popular Rooftop Cinema Club in summer, yet still makes a prime year-round choice thanks to blend of location, modern loft-inspired rooms and reasonable rates. $235 USD per night.
The Publishing House B&B - With just 11 rooms, this boutique B&B in a wonderfully renovated 100+ year old building feels intimate and cozy. It's stylish, but relaxed and unpretentious. It's a good choice if the sometimes corporate feel of many of Chicago's big hotels leaves you uninspired. It's in a good part of the neighborhood too and just a few blocks from the Morgan subway stop. $200 USD per night.
Sonder Market Hall - Sonder is a Spanish hotel group that specializes in budget-to-midrange hotels that punch above their weight and feel a little more stylish than their price point suggests. This one fits the bill; it's not fancy, but it's cute, in a fairly good location, and a great price. It's next to a nightclub though, so best avoided from Thursday to Sunday if you want to get a good night's sleep. $100-150 USD.
6. Wicker Park & Logan Square
Best for: Travelers who like a hipster/bohemian atmosphere, anyone really into live music, breweries, and underground arts and culture
Pros: These are some of the coolest neighborhoods in Chicago
Cons: The hipster appeal can be a bit over-the-top for some, further from downtown (need to use the metro), not super walkable
The "Flatiron” building on Milwaukee Ave in Wicker Park. Photo: Ben Collins-Sussman, CC BY 2.0, via Wikimedia Commons
West of the Chicago River and a good deal away from the skyscrapers of downtown, Wicker Park and Logan Square are two more “alternative” areas that I think are worth considering as potential bases, especially for returning visitors.
Like with Lincoln Park and Lakeview, Wicker Park and Logan Square are adjacent neighborhoods with a lot in common, but also some marked differences. So, I've done the same thing and listed them together, but described them separately.
Wicker Park
I have lived in Wicker Park longer than anywhere else in Chicago. You can call me a hipster if you want but honestly, it’s been decades since bands like the Smashing Pumpkins put this area on the map in the ‘90s. Once a neighborhood of blue-collar workers before becoming a favorite with artists and musicians, these days it’s basically another gentrified cousin of Lincoln Park.
It still holds some of the energy that first made this an attractive area for creative types, but a lot of that has been pushed out as wealthier young people have moved in and rent prices have skyrocketed. While a number of cool dives like Rainbo Club and Innertown Pub remain, and Milwaukee Ave is still full of bars, most of the hipster and independent action has migrated northwest to Logan Square.
This isn't to say that what remains isn't nice (it is - which is why I'm still here!), but it's certainly not the artsy/indie place it was a decade or two ago. In a way, it's a sign of the neighborhood's commercial success that many of the people who kicked off the gentrification have now been pushed out by a new wave of even wealthier residents.
Dotted with low-to-mid rise residential buildings and the type of shops that look independent but often aren’t, the vibe in Wicker Park is still pretty hip and there are lots of great places to browse, shop, eat, listen to live music, and hang out. It's lots of fun, but it definitely sometimes has the feeling of a place that hasn't quite come to terms with its wealth. And if we're being honest, you'll probably find more brunch restaurants now than underground clubs.
While most visitors to the neighborhood come for the dining and nightlife (and that is the most appealing aspect of visiting), it’s a nice area to be at any time of day.
Logan Square
Further north and west of Wicker Park is Logan Square, a neighborhood that people tend to either love or hate.
Primarily a working class neighborhood with large Latino and Polish populations, parts of it – especially along the blue subway line - have changed significantly in the last decade or two. This is an area that's actively undergoing pretty rapid gentrification, which is quite apparent.
The neighborhood's stretch of Milwaukee Avenue is locally known as “Hipster Highway”, and it contains a seemingly endless array of dimly lit cocktail bars and almost too cool restaurants. The area around here is quite different from the rest of the neighborhood, which quickly becomes much more blue collar as you move west from the subway line.
Most of the housing in Logan Square is detached multi-family homes and small brick apartments built along wide boulevards that are lined with a series of interconnected greenways/parks. There’s a good deal of street art, a smattering of shops and little art galleries, and then lots of restaurants and bars on the main avenues. If you like Mexican food, taquerias are omnipresent.
Both neighborhoods have decent public transit to downtown via the Blue Line, but it’s much more car-centric than anywhere else I’ve recommended in this guide, and cars or Ubers are the most common way to get around.
I come here often for a night out, but be warned, daytime is pretty quiet and the commute to/from downtown if traveling by car can be brutal. If you stay near one of the metro stops, you’ll be able to get into the city center in around 20-30 minutes though.
In general, I recommend this area for those seeking a more “authentic” and offbeat Chicago experience centered around food and nightlife. Just know that it’s definitely not a good choice for visitors with just a couple days or who plan to spend a lot of time downtown.
Where to stay
The Robey - It doesn’t get much cooler than this Art Deco masterpiece right in the center of Wicker Park. Located on the corner of Milwaukee, North, and Damen Avenues, you're in the middle of all the action, but don't even need to leave the hotel for great bars. You’ve got your pick of cocktail bars from the pool-equipped Solana on the sixth floor to the 13th floor rooftop gem Up Room (nighttime views are amazing). You'll want a camera just for photos of the hotel! $260 USD per night.
Hyatt Place Wicker Park - A 15-minute walk to Wicker Park's main action (and the subway), this Hyatt makes up for that with big new rooms, a good breakfast, and a great rooftop. Just keep in mind that you'll probably wind up calling Ubers a fair deal if you stay here. $200-300 USD per night.
Wicker Park Inn - This endlessly cute space located on a quiet tree-lined street a few blocks from the Wicker Park madness may be one of Chicago’s best-kept secrets. Vibrant B&B-styled accommodations combined with a relaxing outdoor garden make this the perfect place to relax and take a break from sightseeing, partying, or whatever else you get up to. $230 USD per night.
Longman & Eagle - Want to crash above a rowdy whiskey bar in a room with your own cassette tape console and accompanying mixtapes? If you’re staying in Logan Square, of course you do! There are only 6 rooms, so no last-minute bookings here… The restaurant on the ground floor is also one of Logan Square’s most popular, so fine dining is iterally, right downstairs. $125+ USD per night.
7. South Loop & McCormick Place
Best for: Anyone here on business, families with kids, those valuing proximity to museums, Soldier Field, or major music venues
Pros: Close to downtown, slightly more affordable, more of a neighborhood feel than the Loop (in the northern half of the neighborhood)
Cons: Not very atmospheric, a bit empty around McCormick Place, some areas can feel a little sketchy at night
A block in the northern section of the South Loop. Photo: David Wilson from Oak Park, Illinois, USA, CC BY 2.0, via Wikimedia Commons
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A view of the Field Museum looking towards downtown with Grant Park on the left and Lake Michigan on the right. Photo: Sea Cow, CC BY-SA 4.0, via Wikimedia Commons
Less business-oriented than the Loop neighborhoods to the north, South Loop offers a convenient mix of location, affordability, and access to some major sights. It’s an area with a lot of recent development that is drawing a mix of young families, professionals, and university students (Columbia College is here).
With a commercial base that has been trending more residential in recent years, the main draw is the ara’s close proximity to Chicago’s “Museum Campus” which includes a trio of top local museums (Field Museum, Adler Planetarium, and Shedd Aquarium) which are all worthy stops for any first-time visitor.
The northern part of the neighborhood, near the Museum of Contemporary Art, feels pretty similar to downtown with a mix of high-rise apartments and office buildings. The vibe is different though as a lot of the architecture is older, so you’ll see more brick and much less steel and glass. Close to the museums and adjacent to a massive park and the lakefront, you have very good access to green spaces.
As you head south of Soldier Field, it gets pretty spread out and a bit industrial. This is the convention district and while it’s being heavily developed, it’s still pretty empty. Because of the convention centers and music venues, it has a bunch of large and reasonably priced hotels, so makes sense as a base if you’re in town for work or a nearby show. For those here on sightseeing, stick to the northern part of the neighborhood.
If you’re here in summer or fall, you’ll want to get a taste of local culture when the Chicago Bears are playing at Soldier Field (or in summer, when large bands like the Rolling Stones tour here.) One of the best things about this area is its proximity to Chicago’s Chinatown neighborhood (at its southwestern edge), where you could spend hours sampling authentic Chinese delights along Wentworth Avenue. While there, be sure to check out Ping Tom Memorial Park, a great green space right along the Chicago River.
The area is also home to some of Chicago’s most iconic music venues, from the storied Buddy Guy’s Legends (owned by the 88-year-old Chicago blues master, who can still be occasionally spotted on stage) to the hard-edge punk rock vibes of Reggie’s Rock Club, which also hosts fun party buses to and from local sports games and concerts.
I like to come here for live music events and to visit family-run local businesses like Printer’s Row Wine Shop (owned by my family!), and I generally think the South Loop offers much of what you’ll find in the Loop and River North but at more affordable rates. With parts of the area still developing, however, it can feel a bit empty in the evenings and some parts of it are not super pleasant to walk around late at night.
In general, the northern part of the neighborhood closer to downtown is quite nice, whereas the southern half, around McCormick Place, is functional, but not real pleasant.
Where to stay
Wheeler Mansion - I mean, who wouldn’t want to stay in a mansion? This historic space offers a nice break from the downtown hotel sameness with a small town B&B feel surrounded by towering skyscrapers. Bottom line: this looks like the kind of place the cast from Succession might stay. $600 USD per night.
Marriott Marquis Chicago - Anyone in town for business at McCormick Place, yet still wanting to leave time for some museum sightseeing, should look no further than this 4-star beauty located steps from Wintrust Arena and Soldier Field. If you’re here for work, see if your boss will let you rent out the eye-popping rooftop event space, Level 33, to impress clients. Call it a work expense. $380-500 USD per night.
The Blackstone - Another of my favorite hotels in the city is this historic stunner complete with marble staircases and chic furnishings steps from Grant Park, but far enough from the hustle and bustle to be quiet. Blackstone is also home to one of Chicago’s top restaurants, the Catalan-inspired Mercat a la Planxa, from local celebrity chef Rick Bayless. $250-350 USD per night.
Hilton Chicago - Opened in 1927 in a spectacular downtown location across from Grant Park, this versatile 1,544-room hotel is a top choice for anyone from business travelers to Lollapalooza revelers. Basic rooms are nothing to write home about, but the slight upgrade to a lakeside view room is well worth it. $260 USD per night.