Where to stay in Chicago

See more of Chicago when you stay in one of these dynamic neighborhoods
Photograph: CC/Flickr/vxla
By Time Out Chicago editors |
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Chicago is affectionately known as the city of neighborhoods—there are 77, to be exact. Each community has its own identity, which can be a blessing and a curse for incoming explorers. On one hand, there's no shortage of amazing, personalized experiences to be had in Chicago; on the other, it can be impossible to choose just one place to stay while you're here. The good news is that the city's sprawling public transportation system makes it easy to hop from one 'hood to the next in minutes. To make it simple, we rounded up the very best areas for you to temporarily call home when you visit. These Chicago destinations offer a little bit of everything: top attractions, comfortable accommodation, our favorite restaurants, funky shops and tons of personality.

Where to stay in Chicago

Logan Square
Photograph: Wendell Remington

Logan Square

Boasting gorgeous boulevards and a constantly expanding 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 record lovers, musicians, pinball wizards and dining aficionados to this scenic 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

One of several reasons Chicago was named Best Restaurant City in America in 2017 by Bon Appetit, this cozy Mexican restaurant is helmed by chef Diana Dávila. A quick glance at the menu will have you craving tacos, but we recommend saving most of your calories for the antojos section, where you'll find fish with a bright, satisfying mole and tiny half-moon–shaped, black bean-stuffed enchiladas.

DRINK

Lost Lake

A trip to Logan Square isn't complete without a stop at this popular tiki hideaway. Sip over-the-top drinks decked out in banana dolphins, colorful bendy straws and edible flowers. After a few rum-soaked sippers, trek to Best Intentions to cap off the night with a few beers on the patio.

DO 

Logan Square Farmers Market

Rain or shine, summer or winter, 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.

STAY

Longman & Eagle

Known for its killer brunch menu, Longman & Eagle is also home to a quaint upstairs hotel, 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.

If you do just one thing... 

Spend the afternoon sipping pisco- and mezcal-spiked cocktails at sunny Estereo.

Los Comales
Photograph: Jaclyn Rivas

Pilsen

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 Southwest Side 'hood and enjoy all the culture and entertainment it has to offer.

EAT

HaiSous

First things first: 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

Moody Tongue

Beer nerds will go nuts for this culinary-focused brewpub that offers pours of Steeped Emperor's Lemon Saison, Caramelized Chocolate Churro Baltic Porter and Peeled Grapefruit Pilsner. The two food items available—oysters and chocolate cake—pair perfectly with everything on tap.

DO 

The National Museum of Mexican Art

This underrated Chicago attraction houses an impressive 10,000-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-box hotels northeast of Pilsen in the Loop, but renting a pad for the weekend is your best bet for an immersive experience.

If you do just one thing... 

Take a self-guided, mural-hunting tour through the neighborhood. 

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Photograph: Colin Beckett

West Loop

If you want to be in the loop about everything fun happening in Chicago, you need to stay in the Loop – the West Loop to be precise. This little box of joy contains a lot of the city’s best eateries, bars, shops and more. Plus, it’s incredibly well connected, with the Pink, Green and Blue lines stopping at various points circling the area.

EAT

Monteverde

As we already mentioned, you can eat extremely well in the West Loop. Monteverde (Green Mountain, if you want to know) is a particular highlight. This Italian fusion restaurant was opened by Top Chef contestant Sarah Grueneberg in 2015 to put a tasteful twist on traditional Italian fare.

DRINK

RM Champagne Salon

You may have to wander down an unmarked alleyway to get to RM Champagne Salon, but brave it. If you do you’ll be rewarded by twinkling fairy lights, Parisian chic and very drinkable glasses of Champagne you’ve never heard of. Snacks come in the way of oysters, steak frites and bite-size macarons.

DO

Randolph Street Market

More than 100 vendors hawk their antique housewares, furniture, ephemera, clothing and more at this indoor/outdoor monthly market. Spend some time investigating the vintage clothes and jewelry thoroughly, take part in the vinyl swap and enjoy a spot of lunch at the fancy food stalls.

STAY

Ace Hotel Chicago

Composed of concrete and steel, there’s an industrial feel to this hotel. Yet despite all the exposed raw materials, it remains homely and welcoming. As well as an onsite restaurant, rooftop garden and 24-hour gym, each room also comes with a record player and a small, hand-picked collection of vinyl, a Bluetooth radio and fully stocked minifridge.

If you do just one thing... 

Join a walking tour out east in the Loop, where you can also take in the architecture from a boat cruise along Chicago Harbor.

Wicker Park Fest 2017
Photograph: Neal O'Bryan

Wicker Park and Bucktown

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 its many "house rules" (no cell phone use, no baseball hats, no light beer). Saddle up and see where Chicago's famed craft scene was born while tasting the menu of classic shaken and stirred concoctions. 

DO

606

For an active and totally free afternoon, hop on the 606 (or 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, 69-room hotel is a shiny new addition to 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.

If you do just one thing... 

Knock out five neighborhood restaurants on a three-hour food tour of Wicker Park and Bucktown.

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Hopleaf in Andersonville
Photograph: Jason Little

Andersonville

Small though it may be, Andersonville packs in as much as it possibly can. Here you’ll find unique buys in cool vintage stores next to independent bars and live gig venues. Take advantage of the nightlife scene while you’re here, take in some comedy or a theater show and during the day visit the museums and art galleries.

EAT

First Slice Pie Cafe

Spoil your dinner with a slice of sweetness at this quaint pie shop and café—we're big fans of Michigan cherry, French silk and key lime. Don't have a sweet tooth? The turkey chili and curry chicken salad are stellar savory options.

DRINK

Hopleaf

If you value dinner just as much as you do an ice-cold glass of beer, saddle up at this bustling neighborhood favorite. The mile-long draft list includes cider, mead and pours from near and far. Each Chicago-made beer is marked with the city flag, making it easy for you to drink local all night.

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.

STAY

The Guesthouse Hotel

Steps away from the action, this posh inn offers two- and three-bedroom suites that are perfect for families, small groups and guests traveling with pups. 

If you do just one thing... 

Take in a "barrage of two-minute plays" at the Neo-Futurists' The Infinite Wrench on Fridays and Saturdays at 11:30pm and Sundays at 7pm.

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