Where to Stay, Play, and Eat in Chicago

A Midwesterner recommends how to make the most of your next trip to Chicago, whether you’re here for the culture and design, the food scene, or business mixed with pleasure.

|

Photo Courtesy Photo Spirit / Shutterstock

In 1893, the Ferris wheel was introduced at the Chicago World’s Fair, soaring riders 264 feet into the air, where they could catch a bird’s-eye view of Lake Michigan. It’s also when brownies made their debut, thanks to a dessert-loving local hotelier. This innovative spirit has continued to push Chicago forward, helping to create a metropolis that combines the best of big-city culture with laid-back Midwestern hospitality.

Chicago counts a lakefront that stretches 28 miles, more than 7,300 places to eat, eight major league sports teams, and upwards of 200 theaters. It’s a city that comes to life from one season to the next; summer brings festivals and outdoor activities galore, while winter encourages you to wander through one of the many world-class museums or sip brandy beside a fireplace.

Whatever the timing and inspiration for your trip, one thing’s certain: The Windy City is ready to show you a good time. To get your wanderlust going, we’ve laid out three approaches to exploring Chicago — for art loversfoodies, and bleisure travelers.

Read on for our recommendations and to find out about the benefits that eligible Card Members can enjoy throughout your journey when you book through American Express Travel®.

If you love the arts...

STAY

If you travel to eat...

STAY

EAT

Powdered sugar forms a sun on a small, circular cake baked to a deep golden brown and arrayed on a leaf and woven placemat.

Kasama

Owners Genie Kwon and Timothy Flores opened Kasama as a daytime café in summer 2020, serving French pastries and Filipino fare. The following year, they tacked on limited dinner service (only 14 tables to accommodate pandemic safeguards). Kasama has since become one of Chicago’s most sought-after tasting menus, with 13 courses inspired by the Filipino food Flores grew up eating. They might include pancit, a traditional stir-fried noodle that Flores prepares with scallop conserva, squid ink, crab paste miso, and shaved cured mullet roe. Or kinilaw, a marinated raw seafood dish made here with caviar, hamachi, pandan- and lemongrass-infused coconut milk, and calamansi vinegar. Kwon, as pastry chef, flexes her skills in concocting sweet and savory desserts like black truffle croissants. In 2022, Michelin took notice, and Kasama became the first Filipino restaurant in the world to receive one star.

If you're here for bleisure...

STAY

EAT

A thick, bone-in cut of meat rests on a cast-iron pan, flanked by small red and yellow tomatoes, broccolini, and radicchio.

Monteverde Restaurant & Pastificio

If you’re looking to impress a client or boss, snagging a reservation at Monteverde Restaurant & Pastificio usually does the trick. Sure, it might mean setting a reminder for midnight 30 days beforehand, when reservations open up on Resy, and being quick on the draw, but it’ll be a testament to your drive and dedication. The restaurant, owned by Top Chef alum and James Beard award winner Sarah Grueneberg, delivers magic at lunch and dinner. The big attraction is pasta, made to order on a raised stage in the dining room. Popular picks include the Cacio Whey Pepe (ricotta whey is used to emulsify the sauce, giving it a slight tang) and the gnocchetti with pesto and housemade ricotta. The wine list leans strongly Italian and includes sparkling wines for celebrating.

DRINK

A deep-red cocktail in a gold-rimmed coupe rests on a darkly mirrored bar, with candles and other drinks barely visible in the background.

Milk Room

For a chance to taste a cocktail that may never exist again, head to Milk Room, an eight-seat microbar on the second floor of the Chicago Athletic Association hotel. Rare whiskies and vintage spirits are the draw here, and the uber knowledgeable bartender is happy to guide you through the pages of offerings. You can order neat pours from bottles like a 1950s Jim Beam or an Old Fitzgerald Bottled-in-Bond. New options are added regularly, meaning every visit can be a fresh experience. As for those last-chance mixed drinks: Because of the unique nature of many of the spirts, you may get the final drops from a bottle that can’t be replaced — all the more reason to go big on a Sazerac with Depression-era Pernod.

Looking for more luxury hotels in Chicago?
Don't Live Life Without It