Our Favorite Places to Eat, Sleep, and Explore in Chicago

Highlights include the world’s first Michelin-star Filipino restaurant and an unforgettable river cruise.

Chicago, IL is America’s third-largest city and a global hub for art, architecture, fine dining, and more. This is a city divided into 77 neighborhoods spread across 234 square miles, a place where famous skyscrapers rise from an iconic skyline at the edge of Lake Michigan.

With more than 7,000 restaurants, 450 live entertainment venues, and countless adventures to be had, there’s way more to do in Chicago than you might expect. Ride a Ferris wheel in the city where Ferris wheels were invented. Head to the top of a towering skyscraper in the city where the world’s first skyscraper was built. Learn what differentiates a Chicago hot dog from the rest, or tuck into a warm, cheesy, deep-dish pizza.

There’s so much to eat, see, and do in the Windy City that figuring out where to start is going to be tough. But that’s why you’re here—hello, nice to meet you, consider this your friendly guide to doing Chicago right.

From the world’s first Michelin-starred Filipino restaurant to the most luxurious hotels downtown and the local icons you can’t miss, we’ve rounded up some of our places to stay, eat, drink, and play in Chicago.

Where to stay

With around 1,000 hotels in the city, there is a perfect room for everyone in Chicago. In the Fulton Market neighborhood, Nobu Hotel is just a block from Au Cheval—home of Chicago’s most legendary cheeseburger—and Stephanie Izard’s Girl & The Goat. The hotel is home to 115 Japanese-inspired rooms and an iconic Nobu restaurant. For live music and a nightcap, City Winery is a few blocks away.

You’ll find one of Chicago’s newest luxury hotels at the edge of Lake Michigan. The St. Regis Chicago soars more than 100 stories, making it the third-tallest skyscraper in the city. This is an ideal home base for exploring the city’s top museums or sampling some of the city’s best Japanese and Italian fare. The St. Regis is home to the sushi restaurant Miru and Tre Dita, a Tuscan steakhouse from Chef Evan Funke.

If you’re looking to stay blocks from some of the best steakhouses in Chicago, consider the Park Hyatt on Michigan Avenue. This newly renovated hotel is steps from some of the best shopping on the Magnificent Mile and just a few blocks from Gibsons and Maple & Ash—two of Chicago’s top steakhouses. Alternatively, we’ll never discourage a night in—at this property, you can feast on sushi or a seafood tower at the on-site restaurant NoMI.

If you prefer historic hotels, check into the Chicago Athletic Association Hotel, part of the Unbound Collection by Hyatt. Walking into this hotel is like stepping back in time—the property was constructed for the 1893 World’s Fair and designed to resemble the Doge Palace in Venice. Rooms feature every modern convenience and special touches like boxing-inspired robes. While you’re here, pop into the Milk Room, a tiny speakeasy with one of the finest collections of rare spirits in the world.

Where to eat

Chicago is one of the best food cities in the United States. Whether it's fine dining, a beloved local lunch spot, or cuisine from a far-flung nation you’re craving, you’ll find it here. For a Michelin-star Indian meal, head to Indienne from Chef Sujan Sarkar. The River North restaurant opened in late 2022 and offers a six-course menu that doubles as an adventure across the subcontinent. Past menu items have included pani puri (a traditional Indian street food), foie gras kebabs, and egg curry with lobster. Even better: vegan, vegetarian, and non-vegetarian tasting menus are available with an optional wine pairing.

Or try Kasama, the world’s first Michelin-starred Filipino restaurant. By day, Kasama is a buzzy brunch counter serving up hearty Filipino breakfasts, adobos, and sandwiches. Once the sun goes down, it transforms into a fine dining venue with a $265 tasting menu. For an unforgettable fine-dining experience inspired by art, head to Esme in Lincoln Park. This intimate Michelin-starred restaurant from Chef Jenner Tomaska works with a new artist every few months to design a tasting menu inspired by their work. Tomaska’s dishes themselves are works of art, sometimes delivered with almost theatrical performances. If you can’t score a reservation for the tasting menu, head to Bar Esme for a craft cocktail and the signature hot Cheetos.

For a more casual Mexican meal, head to Mi Tocaya Antojeria in Logan Square. Owner Diana Davila, a Chicago native and James Beard-nominated chef, describes her restaurant as an homage to women and ancestors. The menu, inspired by Davila’s culinary training in Oaxaca and travels in Mexico, features items like smoked beer-can chicken tacos and a DIY quesa birria.

Things to do

From art and architecture to festivals to wineries, there’s always something to do in Chicago—even in the blustery winter months. The Art Institute of Chicago, one of the best art museums in the U.S., is home to some of the most recognizable masterpieces in the world (think paintings you saw in your high school history books). This is where you'll find icons like Grant Wood's American Gothic, Edward Hopper's Nighthawks, and George Seurat's A Sunday on La Grande Jatte. It’s also home to pieces by Vincent Van Gogh, Pablo Picasso, and Claude Monet.

Step on board Chicago’s First Lady for a Chicago Architecture Foundation river cruise. Sail through decades of architectural history, passing icons including the Gothic Revival Tribune Tower, the London Guarantee Building, and the Merchandise Mart, once the largest building in the world. Guides will share stories about each building, as well as other design notes, as you cut through town. Tours are 90 minutes long and offered between March and November.

The city is big on nightlife. Get to know some of the world’s best Black-owned wineries by sipping on wine flights at the Bronzeville Winery. The Black on Black flight, which features wine from four different Black-owned wine brands, is one of the most popular items on the menu. If you come for brunch, try the Ube latte. And if you’re a vegan, don’t miss the watermelon nigiri, which is soaked and brined overnight and served over coconut rice.

If your travel dates are flexible, strongly consider visiting during September, when you can eat your way across Chicago without having to leave iconic Millennium Park. Every fall, the park plays host to Chicago Gourmet, an upscale food and wine festival that features appearances by some of the city’s top chefs. Dig into the city’s best burgers, toast your trip with tacos and tequila, or sample some of the world’s finest wines and spirits. This festival is an embodiment of the festive spirit that exists in Chicago year-round—Midwest Nice is real, and you’ll have no trouble making a friend or two wherever you end up.

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