Where to stay in Chicago to experience the best areas and places

Boasting gorgeous boulevards and a growing selection of restaurants and bars, Logan Square is one of the city's trendiest neighborhoods, balancing family-friendly amenities with a thriving nightlife. The variety of diversions attracts vinyl lovers, musicians, pinball wizards and dining aficionados to this scenic (and rapidly-changing) section of Chicago. Logan Square is best suited for return visitors who have already hit the major tourist sites downtown. Centrally located around two Blue Line stations and plenty of buses, it's easy to bounce around to other popular 'hoods like Wicker Park, West Town and the Loop.

EAT

Mi Tocaya Antojería

Forget everything you thought you knew about Mexican food and allow chef Diana Dávila to wow you with soul-warming dishes like fried oyster tacos, chile ash-dusted guacamole and braised pork shank swimming in luscious mole. Finish your meal with a slice of legendary tres leches cake from South Side bakery Kristoffer's.

DRINK

Pilot Project

Why settle for visiting one brewery when you could sample beer some several different creators in this incuabator space? Home to six different breweries (Funkytown, Flora, Azadi, Rovm Hard Kombucha, Donna's Pickle Beer and Brewer's Kitchen), Pilot Project boasts a sleek indoor lounge and a spacious patio. Sip the latest hazy IPAs and fruited sours before browsing a selection of cans that you can purchase and enjoy at home. If you'd rather have a cocktail, the Whister or Billy Sunday are great options.

DO 

Logan Square Farmers Market

Rain or shine, this expansive market draws vendors from Wisconsin, Michigan and southern Illinois. Beyond oodles of fresh produce, visitors can buy handmade soaps, empanadas, tacos, flowers, hot sauce and so much more. During the market’s outdoor season, it’s easy to grab some food and find a spot on Logan Square’s gorgeous boulevards to enjoy it.

STAY

Longman & Eagle

Known for its killer whiskey menu, Longman & Eagle is also home to a quaint upstairs hotel (simply known as “the INN”), where rooms are outfitted with stand-alone tubs, exposed brick and unique pieces of art. Book early to ensure a spot at this sweet inn—and be aware that you’ll be sleeping above a working bar, so those with early bedtimes might want to look elsewhere.

Pilsen is one of the most recognizable neighborhoods in the city. With its distinct murals and vibrant public art, it's not hard to see the artistic culture that's present in Chicago's Southwest Side. Home to one of the best museums in the city, some fantastic contemporary art galleries and a booming bar and restaurant scene to boot, Pilsen has everything a fun and culture-loving visitor could desire. It's accessible by way of bus, Pink Line, Metra or a quick hop off of the Eisenhower, Dan Ryan or Stevenson Expressways. Head to the gorgeous 'hood and enjoy all the culture and entertainment it has to offer.

EAT

HaiSous

Be sure to nab a reservation at this Vietnamese restaurant with plenty of curious and familiar bites, including fish sauce-glazed chicken wings and tender mussels cooked in coconut broth. For lunch the next day, hit the neighborhood's endless supply of taco joints and enjoy a quick, casual bite (we're particularly fond of Taqueria Los Comales and Carnitas Uruapan).

DRINK

Punch House

Guests are transported to a funky, 70s-era basement as soon as they walk into Punch House, which is located below Dusek's Tavern inside Thalia Hall. As its name suggests, this watering hole specializes in punch, so bring a friend or three to help you polish off a large-format cocktail.

DO 

The National Museum of Mexican Art

This underrated Chicago attraction houses an impressive 12,000-piece permanent collection, rotating exhibits and family-friendly workshops. The best part? Admission is always free.

STAY

Book an Airbnb

There are plenty of big-name hotels northeast of Pilsen in the Loop, but renting a pad for the weekend is your best bet for an immersive experience.

If you fancy yourself a foodie, there's no better place to stay than the West Loop. The neighborhood is known for its abundance of excellent restaurants and bars, including a handful of Michelin-starred kitchens like Oriole and Ever. Plus, you won't have to go far to explore must-see attractions downtown—the Loop is just a train ride away.

EAT

Time Out Market Chicago

Time Out Market Chicago brings together some of the city's best chefs under one roof, serving everything from comforting pastas and tender brisket to steaming bowls of ramen and one of the best burgers in Chicago. Time Out editors curate the entire lineup of vendors, hand-selecting the top chefs from around the city to cook with us. If you have time for just one dining experience, make it Time Out Market Chicago.

DRINK

Moneygun

Located on the east side of the Kennedy Expressway, this West Loop spot specializes in classic cocktails—41 to be exact. Sip sidecars, cosmopolitans, mojitos, negronis and martinis for $13.50 each, which is a steal when you consider the bar team is using house-made syrups, sodas and elixirs to craft perfectly balanced sippers.

DO

WNDR Museum

The rule in most museums is look, but don’t come even close to touching. That’s thrown out the window at WNDR Museum, which is more like an immersive experience versus a traditional art museum. The museum began as a pop-up in 2018, but has since expanded and put down permanent roots, with dozens of exhibits, including the only Infinity Mirror Room (created by Japanese artist Yayoi Kusama) in Chicago.

STAY

The Hoxton

Located in the heart of the West Loop, the Hoxton puts out-of-town visitors in the thick of things. But there's a good chance you won't want to leave the 182-room hotel thanks to its curated food and beverage offerings, including a rooftop restaurant and bar from famed chef Stephanie Izard as well as a sexy basement bar that slings classic cocktails.

Ah, Wicker Park. That's where they shot High Fidelity. And there was that Wicker Park movie with Josh Hartnett. Wait, who's Josh Hartnett again? Point is, that was years ago. Wicker Park and Bucktown remain a vibrant hub of culture and commerce in Chicago, riddled with boutiques, restaurants, cocktail bars, concerts venues and condos. It's easy to get to from O'Hare Airport and boasts plenty of bus and train options for navigating the rest of your trip.

EAT

Dove's Luncheonette

For brunch, pop over to this insanely sweet (albeit cozy) eatery for Instagrammable southern-inspired Mexican fare. The 41-stool diner serves massive portions of hangover-curing goodies like buttermilk fried chicken smothered in chorizo verde gravy and showered in sweet peas and pearl onions. Whatever you do, don't skip the Bloody Mary.

DRINK

Violet Hour

Mixology buffs will appreciate the attention to detail at this dark and sexy cocktail den that's known for discouraging cell phone use. Saddle up and see where Chicago's famed craft scene was born while tasting the menu of classic shaken and stirred concoctions.

DO

The 606

For an active and totally free afternoon, hop on the 606 (a.k.a. the Bloomingdale Trail), an urban walkway that stretches across several surrounding 'hoods. It's easy to hop on and off to explore shops, parks and coffee shops located just off the trail.

STAY

The Robey

This 12-story, 89-room hotel is the premiere place to stay in Wicker Park. The Robey's centralized location is easily its biggest perk and allows visitors to see the best of the neighborhood without going far. Design enthusiasts will get a kick out of the mid-century modern design touches, while foodies will adore Cafe Robey, the underrated first-floor restaurant.

Anyone who’s ever been to Chicago will invariably end up in River North at some point. Bursting with nightlife and food-and-drink options, the bustling neighborhood has something for everyone. You’re just steps away from the city’s premier shopping district—the Magnificent Mile—as well as an amazing art scene. River North is also close to several other popular areas, including West Loop and Gold Coast. And it’s easily accessible by train and bus if you need to venture further out.

EAT

Bavette's

There’s no shortage of fantastic restaurants in the area—especially ones specializing in steak. No city has a better collection of chophouses than Chicago, and Bavette’s is arguably the best of the bunch. Hogsalt Hospitality’s vaguely French steakhouse—decked out with jazz-era decor and music—is a sultry and charming experience. Diners need not be huge fans of beef to get a good meal; in fact, as good as the steak frites is, both the fried and roasted chicken are just as good. Elegant cocktails begin meals here; fabulous pies (lemon meringue, chocolate cream) end them.

DRINK

Green Door Tavern

Established in 1921, Green Door Tavern is one of the oldest watering holes in Chicago. The menu offers elevated bar fare (think Scotch eggs, Chicago-style poutine and deviled eggs), cocktails offer riffs on classics and the beer and whiskey lists are impressive. Pop by The Drifter, the basement bar that's located in the old speakeasy section of the bar, for a nightcap.

DO

Museum of Contemporary Art

Among the largest institutions in the world dedicated to art created post-1950, the Museum of Contemporary Art is best known for hosting major touring exhibitions, including past exhibitions celebrating luminaries like Virgil Abloh, David Bowie and Takashi Murakami. Throughout the MCA's galleries, you'll also find exhibits dedicated to rising local and international artists (including the museum's ongoing Chicago Works series). Once you're finished strolling through the galleries, make sure to exit through the well-curated gift shop.

STAY

The Peninsula Chicago

Treat yourself to a relaxing vacation at the five-star Peninsula Chicago. Located along the Mag Mile, the hotel boasts 339 rooms decked out in simple and chic décor, with bedside tablets that let guests adjust the temperature, lighting and music in their cozy quarters. Stay active thanks to a state-of-the-art fitness center and glass-enclosed pool with views of Lake Michigan or enjoy afternoon tea in the elegant Lobby. The 20-foot-high, floor-to-ceiling windows overlook an al fresco dining area attached to the Shanghai Terrace restaurant, serving dim sum and more Asian-inspired fare in a smart-casual setting.

Lincoln Park is one of the most affluent neighborhoods in the city and home to an eponymous 1,200-acre park. Thanks to its close proximity to Lake Michigan and the Loop, it's a popular spot for commuters who want to enjoy the neighborhood lifestyle just a few train stops away from Chicago's urban center. If you're visiting, you'll find a host of restaurants, theaters, museums, bars and shops to explore, plus beaches, a zoo and a conservatory for nature lovers.

EAT

Boka

In its 19-plus years on Halsted Street, Boka has racked up a trophy case worth of awards, including one long-standing Michelin star and a handful of Jean Banchet Awards. But we prefer to let chef-partner Lee Wolen’s impeccable techniques—on everything from dry-aged duck and roasted chicken to parsnip agnolotti—do the talking. It'd be a shame to skip dessert from pastry chef Kim Mok, who whips up dreamy, sugar-filled confections with serious range—from roasted rhubarb to chocolate angel food cake.

DRINK

Delilah's

No Chicago bar list is complete without Mike Miller’s no-bullshit establishment, which is known for its extensive collection of whiskey and beer as well as its nightly DJ sets—everything from metal to ska (the good kind) and R&B—as well as VHS tape screenings. Miller holds court at the nearly three-decade-old bar, which is decorated with red Christmas lights, obscure works from local artists, a well-loved pool table and a pinball machine. If the more than 800 options on the whiskey list are too intimidating, don't be afraid to ask the bartender for a recommendation.

DO

The Second City

Even if you know nothing about improv, chances are you've heard of Second City. This is the place that put both sketch and improvised comedy on the map while launching the careers of many distinguished comics including Bill Murray, Tina Fey, Chris Farley, John Belushi, Joan Rivers, Stephen Colbert and Steve Carell. Mainstage revues are occasionally stodgy, but most shows are still top-notch.

STAY

Hotel Lincoln

This boutique hotel offers 184 guest rooms, clever artwork (quirky paintings on a lobby wall were sourced from Lincoln Park yard sales), a coffee shop and two sushi concepts—Sushi Suite 202 and Sushi By Bou. If that’s not enough, the rooftop bar, The J. Parker, is a lively spot to grab a drink and take in sweeping views of the skyline and park.

Small though it may be, Andersonville is a Far North Side neighborhood with plenty of personality and no shortage of ways for visitors to stay occupied. Walk along the bustling Clark Street corridor and you’ll find unique buys in cool vintage stores next to cozy bars, neighborhood restaurants and theaters where you can see comedy and magic. There are few better spots for LGBTQ+ nightlife in all of Chicago—and the Red Line is nearby if you want to explore the rest of the city.

EAT

Anteprima

Yes, Andersonville is a traditionally Swedish neighborhood, but the area's culinary delights span the globe, exmplified by this bustling, rustic Italian trattoria. The menu at Anteprima rotates with the seasons, but you can always count on fresh, homemade pasta. For a truly authentic Italian-American experience, give nonna the day off and pick up a Sunday supper.

DRINK

Hopleaf

If you value dinner just as much as you do a cold glass of beer, find a table at this bustling neighborhood favorite. The mile-long draft list includes cider, mead and pours from around the world, including a formidable selection of Belgian beers. Each Chicago-made beer on the menu is marked with the city flag, making it easy for you to drink local all night. And if you need a snack, we recommend the Belgian-style mussels with pommes frites.

DO 

Andersonville Galleria

Dozens of local vendors occupy this unique shopping hub where you can browse jewelry, apparel, candles, paper goods, prints and furniture without leaving the building. When you do come up for air, there are plenty of locally-owned shops in the surrounding blocks to explore, including Rattleback Records and Scout.

STAY

The Guesthouse Hotel

Steps away from the action farther north on Clark Street, this posh inn offers two- and three-bedroom suites that are perfect for families, small groups and guests traveling with pups. Its location on the edge of Andersonville makes it easy to explore Uptown and the Asian restaurants on Argyle Street.

Home to the University of Chicago, the Museum of Science and Industry and the Obama family (before they moved to the White House), Hyde Park is one of the city’s most historic neighborhoods. Not far from the Dan Ryan Expressway and the Metra Electric line, this South Side neighborhood boasts gorgeous parks (Washington Park to the West, Jackson Park to the South) and easy access to the lakefront. Whether you’re soaking in the views of the skyline from Promontory Point or exploring 53rd Street, this collegiate ‘hood is a great place to stay if you’ve already hit the major tourist attractions in the Loop.

EAT

Virtue

A relatively new addition to Chicago’s dining scene, the southern-American inspired cuisine at Virtue has been taking guests on a culinary journey since 2018. Owner and executive chef Erick Williams serves dishes with heart, including gumbo, short ribs and blackened catfish. Make sure to sample the cornbread, made according to Williams's grandmother's recipe and served with sweet honey butter.

DRINK

Woodlawn Tap

There’s nothing like a college bar, and for students at the University of Chicago, that bar is the Woodlawn Tap. Where else can you chow down on cheap burgers and fries while listening to Nobel Prize winners discuss any variety of topics? While it’s official name is the Woodlawn Tap, those in the know refer to the beloved Hyde Park bar as Jimmy’s, in honor of its late owner and barkeep, Jimmy Wilson.

DO

Robie House

While Frank Lloyd Wright’s works are scattered across the country, the famous architect designed many homes in Chicago while living in nearby Oak Park—including Hyde Park’s Frederick C. Robie House. Completed in 1910, the house is now a National Historic Landmark and stands as one of the primary examples of Wright’s Prairie style of architecture. Admire the clean lines from the outside, or buy tickets to take a tour through the Frank Lloyd Wright Trust.

STAY

The Study

The thing about staying in Hyde Park is that you’re bound to run into a lot of University of Chicago students and professors. The Study understands and embraces that, with locations adjacent to the campuses of Yale University and the University of Pennsylvania. Its Hyde Park hotel features 167 rooms, a lounge area filled with books and publications as well as several event and conference spaces. The rooms come with feather-topped beds, modern bathrooms and some picturesque views of the university.

As its name suggests, if you’re heading to Chicago to take in Lake Michigan, you can’t do much better than Lakeview. The neighborhood doesn’t boast the lengthy beaches that other ‘hoods brag about, but it is home to Belmont Harbor Dog Beach, a sandy nook alongside the ships that dock at Belmont Harbor that’s a great spot for pup viewing when the weather is warmer. It also has just about everything else to satisfy any traveler’s needs, including the lively Northalsted area, home to the annual Pride parade and serveral LGBTQ nightlife destinations.

EAT

Wood

Who says refined dining has to be inaccessible? Case-in-point, Wood. Helmed by Executive Chef Devin Kreller, this Northalsted spot serves a wide variety of New American cuisine, including confit duck leg, served with Carolina Gold rice and covered with Thai coconut curry. Wood is also renowned for its bar program, including its fun and creative house cocktails, like the Breaking Bad-inspired Heisenberg—a gin drink with crystal blue Hpnotiq ice.

DRINK

Guthries Tavern

There are few places that feel as authentically Chicago as Guthries Tavern, a watering hole that is removed from the craziness of Clark Street, but still close enough that it’s an easy walk after a Cubs game. It’s a spot where Chicagoans have been gathering to drink for decades— although the location has only been called Guthries since the ’80s and recently reopened under new ownership, retaining its craft beer offerings and board game collection.

DO

Music Box Theatre

If you’re looking for somewhere to catch the newest blockbuster, then the Music Box Theatre might not be for you. But if you want to see a Japanese indie film that everyone has been talking about on Twitter, this is probably where it’s playing. Known for its regular repertoire screenings and arthouse programming, the Music Box Theatre is a sanctuary for anyone who loves film. Even if you don’t have time for a movie, you can sit in the adjacent lounge and admire the vintage movie posters on the wall.

STAY

Old Chicago Inn

With 10 guest rooms to choose from and a location just a few blocks from Wrigley Field, the Vic Theater and many bars and restaurants, the Old Chicago Inn is a great home base for a Lakeview vacation. Don’t feel like going out? The hotel boasts its own Prohibition-style speakeasy (Room 13) serving cocktails that harken back to the roaring ’20s, including the Boulevardier, a bitter-sweet beverage made with a mixture of bourbon, sweet vermouth and amaro. Just ask for the password when you check in.