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)
The grandaddy of Chicago neighborhoods, this is rightfully home base for many first-time visitors. Here, an embarrassment of urban riches awaits; from the world-famous 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, which hosts the rowdy Lollapalooza music festival every summer.
2. River North & Mag Mile (purple above)
The downtown area immediately north of the Chicago River is known (appropriately enough) as River North, home of a high concentration of downtown Chicago bars, restaurants, and clubs. This upscale and nightlife-heavy district borders the world-famous Magnificent Mile, downtown Chicago’s tourist-friendly shopping district along Michigan Avenue. This area also includes the iconic Chicago Riverwalk pedestrian thoroughfare.
3. Streeterville & Gold Coast (green above)
The vibe gets even more posh as you continue north from River North into the bordering areas of Streeterville and Gold Coast, home of some of Chicago’s most visited attractions including the 360 Chicago observation deck and Navy Pier, an expansive shopping and entertainment district most recognizable by its famous Ferris wheel overlooking the lake.
4. 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, lower, and less business-oriented, this is a major dining and nightlife district 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 most posh hotels.
5. 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 second-oldest ballpark in America) and the expansive North Avenue Beach, which bursts to life in the summer with beach volleyball and cocktails on the water.
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 city are top choices for those looking for offbeat arts, divey music clubs, fancy cocktail bars, and trendy restaurants, especially along the “Hipster Highway” of Milwaukee Avenue.
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.
1. The Loop
Best for: First-time visitors seeking a central location for sightseeing
Pros: High concentration of top attractions in a relatively compact area
Cons: Can be quite touristy and crowded, very downtown feel
A boat passing under Du Sable 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 in a gorgeous juxtaposition of our natural and human-made worlds. This center of urban culture and commerce showcases some of the city’s green crown jewels along Lake Michigan including Grant Park and Millennium Park, where there’s year-round action and live music in the summer months.
Yes, this area can be quite touristy and congested during popular events like Lollapalooza or the St. Patrick’s Day Parade, yet its large expanses of parks and green space nicely balance out the noise and hustle-and-bustle of daily urban life. A couple blocks inland from the lake, the Art of Institute of Chicago is a national treasure and a great place to start your exploration of the area.
The landmark Chicago Theatre is one of the city’s most enchanting venues for live music (and a popular spot for photo ops), while a stroll along the Chicago Riverwalk will give you a great sense for the feel of the city as you watch tourist boats glide along the Chicago River besides gleaming sun-dappled skyscrapers. Grab a drink and people watch or, better yet, get on one of the boats! (While touristy, it is still one of my top recommendations for first-timers.)
You can find plenty of cheaper food options from quick-service restaurants catering to the working crowd in addition to fancier, more tourist-oriented options often located inside hotels. The city’s commercial core feels more rushed and goal-focused during the day, while 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.
The neighborhood derives its name from the iconic subway cars that rumble on elevated tracks overhead, making a literal loop around the downtown, so you know it is extremely well-serviced by public transport including trains and buses. Walking down the street, you will see a mix of mostly commercial buildings housing corporations, governmental offices, universities, financial institutions, and bars/restaurants.
While I often visit this area for work-related tasks and errands, I also like to come here 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. I recommend this area to anyone looking for a central district in close proximity to the major sights, although those looking for a more authentic taste of what it’s actually like to live in Chicago should probably head elsewhere.
While this is a bustling commercial district during the day, few people actually live in this area and it can become much more quiet after night falls and workers head back to the more residential neighborhoods. That being said, there’s always something to see here and the location can’t be beat due to ease of transit and a large choice of accommodations.
Where to stay
Chicago Athletic Association: This historic 4-star hotel was once, as the name suggests, home of a local athletic association. Today the renovated hotel is always my first choice for recommendations in the area, thanks to its unbeatable location on Michigan Avenue across from Millenium Park and its nice but not too fancy rooms. But the best part about staying here is 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 over Millennium Park and the lake. $300 USD per night.
LondonHouse: Another historic gem famous for its rooftop bar, this one overlooking the Chicago River and downtown architecture, LondonHouse is a popular spot for summer cocktails in the sun or dance parties after dark. Rooms are elegant yet simple, and they also offer spa treatments for those seeking a bit of extra pampering. $300 USD per night.
Pendry Chicago: Just opened last year to much fanfare inside one of Chicago’s most historically significant buildings, Pendry Chicago also hosts one of the most stunning rooftop bars in Chicago at its 24th floor outpost Chateau Carbide. Inside, Bar Pendry is equally sleek and sexy, with rooms that do the basics well with understated luxury. Great location along Michigan Avenue in between Millennium Park and the Chicago River. $275 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. $175 USD per night.
Virgin Hotel Chicago: A touch of vintage British elegance greets visitors to this lively downtown selection most well known for its 26th-floor rooftop lounge Cerise, one of the area’s most popular weekend clubs. Rooms feature fun unique touches like vintage mini-fridges and exterior doorbells. $260 USD per night.
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
Cons: Expensive, 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
First-time visitors to Chicago will most likely get their first taste of Chicago’s raucous nightlife scene in this lively district north of the Chicago River. But eating and drinking isn’t the only reason tourists flock here. It’s also home of Chicago’s most upscale shopping district, where you can window shop amidst the many luxury stores that line Michigan Avenue’s fabled Magnificent (or “Mag”) Mile.
Here you’ll find some of the city’s most gorgeous architecture, particularly in the Pioneer Court area immediately north of the Chicago River across the DuSable Bridge where historic gems like the Tribune Tower and Wrigley Building can be photographed in all their glory. For a unique after-dark experience, watch art projected onto the exterior façade of the world’s largest commercial building: THE MART.
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 actually come here relatively often at night to visit the bars, restaurants, and music clubs, and it makes a nice area to take visiting friends after seeing the downtown sights.
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, this area is also home to some of Chicago’s finest restaurants and hotels.
I would recommend this area to anyone looking for a lively nightlife district close to the main sights. High-rise apartment complexes for young professionals and creatives make this area feel a bit more residential, with an undercurrent of electric energy that continues well into the night. 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
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. $90 USD per night.
The Godfrey Hotel: This chic outpost is most well trafficked at its I|O Godfrey Roofscape, easily one of Chicago’s most gorgeous patios which also operates year-round thanks to its retractable roof. Rooms are basic but get the job done, and the hotel’s on-site Mediterranean restaurant Yasemi is not to be overlooked. $180 USD per night.
Peninsula Chicago: High-end travelers looking to splurge on 5-star luxury would be wise to add this stunner to their short list, which brings a touch of Far East pampering to the working-class Midwest. Its Z Bar rooftop lounge offers a romantic lookout above Michigan Avenue, while any of its sensibly seductive rooms are fit for a king. $575 USD per night.
Intercontinental Chicago: Those looking for an unbeatable Mag Mile location and luxurious accommodations that won’t break the bank should point their GPS to this lovely hotel just steps from the Chicago Riverwalk and Pioneer Square. Rooms are luxurious but on the small side, yet they also host an ornate Olympic-sized swimming pool on the 14th floor. This is another of my oft-recommended spots for visiting friends and family. $240 USD per night.
The Drake: One of Chicago’s most iconic structures as viewed from Lake Shore Drive, many locals first get to know The Drake at one of their legendary New Year’s Eve parties (which they’ve been throwing since 1920). But you don’t need a special occasion to choose this affordable historic space overlooking Lake Michigan, which is also reportedly one of Chicago’s most haunted hotels. $180 USD per night.
3. Streeterville & Gold Coast
Best for: High end living, beach life, and families with kids
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, home to the overcrowded tourist trap known as Navy Pier, expensive
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. This scenic district extending from Michigan Avenue to Lake Michigan is also 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, I can’t deny the fact that this is a beautiful area that every first-time visitor needs to see up close. Get a bird’s-eye view of the city over the lake from the 360 Chicago observation deck then take a stroll to my favorite beach, the lesser-known Ohio Street Beach, where skyscrapers rise just across from the sand along the legendary Lake Shore Drive.
In summer, congregations of boaters gather off the beach in an area of the lake known as the “Playpen” for booze and beats, while more famous beaches like North Avenue Beach and Oak Street Beach play host to a festive sea of sun-seeking and volleyball. In colder months (or anytime of year), the Museum of Contemporary Art is another must-visit neighborhood attraction.
And then there is the overrun lakeside playground known as Navy Pier. Sure, it’s worth seeing. Get a photo of the Ferris wheel. Check out the massive yachts. Grab a drink at the world’s largest rooftop bar. But please, don’t mistake this for the “real” Chicago. This is tourist central and, as long as you understand that, 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.
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 surrounding area. Yet that may be a plus for those looking for a good location with tree-lined streets and a more residential feel near the lake. Just expect to pay a premium.
Where to stay
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.
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, while its on-site Italian restaurant The Albert is just as inventive. Another of my top recommendations in the city. $265 USD per night.
Viceroy Chicago: My favorite hotel in the city is this elegant yet understated 4-star gem offering one of the best combination lake/city views in the area, best enjoyed from its sexy 18th-floor rooftop lounge Pandan 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.
Acme Hotel Company: This hipster-beloved spot is easily 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. $140 USD per night.
4. West Loop & Fulton Market
Best for: Trendy restaurants and nightlife, bars and clubs, boutique hotels
Pros: Close to downtown but feels like a real neighborhood, lively food and drink scene
Cons: Long walk into downtown (will need to use the metro), not many 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
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.
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.
5. Lincoln Park & Lakeview
Best for: Wealthy residential feel, families, sports fans, local bar culture
Pros: Close to downtown but unique and relaxed neighborhood feel, good dining and bar scene
Cons: Lincoln Park is very expensive, pretty yuppie, and does not have many 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.
6. Wicker Park & Logan Square
Best for: Live music, hipsters, breweries, underground arts and culture
Pros: 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 housed in one of Chicago’s most architecturally significant buildings. Perched right in the center of the Wicker Park action at the bustling corner of Milwaukee, North, and Damen Avenues, 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. Pack a camera. $260 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 actually get some work (and/or thinking) done. $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. Choose from one of six tragically hip rooms perched above one of Logan Square’s most popular restaurants and you’ll fit right in. $125+ USD per night.
7. South Loop & McCormick Place
Best for: Business trips, proximity to museums and large sports/music events
Pros: Close to downtown, slightly more affordable
Cons: Not very atmospheric, empty in places, some areas can feel a bit 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.
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: Those looking to conduct business at McCormick Place, yet still leave time for some museum sightseeing, should look no further than this 4-star beauty located steps from McCormick Place, Wintrust Area, 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 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 ranging 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.
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, yet far enough away from the hustle and bustle. Blackstone is also home to one of Chicago’s top restaurants, the Catalan-inspired Mercat a la Planxa, from local celebrity chef Rick Bayless. $260 USD per night.