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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.

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 lovers, foodies, and bleisure travelers.

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

Chicago Architecture Center River Cruise
Chicago Architecture Center River Cruise
Esmé
Esmé
PLAY

The expert docents from the Chicago Architecture Center (architecture.org) have been leading small-group tours for more than 50 years and know the city’s buildings inside and out. Love Art Deco? Visit select exemplars of the style in the financial district. For fans of Tiffany, a 90-minute tour takes in a variety of art-glass and mosaic installations. If your tastes run more Gothic, discover buildings sporting the style tucked among the urban center’s modern skyscrapers and office buildings. Or opt for one of the more popular outings, a viewing of landmark buildings that line the Chicago River via boat. Those who prefer a more intimate experience can arrange a private tour, which takes you on a trip through topics like the 1893 World’s Fair or the Great Chicago Fire.

EAT

Forget about food as art. While, yes, you could apply that phrase to Esmé, where dinner is filled with colorful and fanciful dishes, the concept behind this fine-dining restaurant in Lincoln Park is more like food and art. The husband-and-wife team of Jenner Tomaska and Katrina Bravo crafts each course so that the menu items and tableware coordinate to tell a culinary story. As with the tasting menu, the art that graces the tables and fills the airy space changes regularly, highlighting local talents. Expect to spend at least 2½ hours enthralled by the various canapés, meat and seafood creations, and desserts (about 14 items in all). If you’re not up for the full experience, you can get a taste of Esmé à la carte in the adjacent Bar Esmé.

Book Esmé on Resy and get special access when you add your eligible American Express® Card to your Resy profile. Terms apply. Learn More.

Soif
Soif
Music Box Theatre
Music Box Theatre
DRINK

In the basement of Testaccio restaurant in Logan Square awaits Soif (soifchicago.com), a dimly lit, scarlet-hued space inspired by the wine bars of Paris (the name means “thirsty”). Owner Aldo Zaninotto, a frequent visitor to the City of Light, obliges with Champagne and French wines, including several natural and hard-to-find picks. While the emphasis is on bottles, there’s also a selection of by-the-glass pours. Cocktails share the same French flair, with spirits such as cognac, calvados, and crème de cassis represented. The food menu is perfect for noshing; expect bites like Foie Gras Brûlée, crème fraiche and chips, caviar, and a meat and cheese plate. The weekends feature a rotating slate of DJs; reservations recommended.

RELAX

No matter the weather, cinephiles can revel in an under-the-stars movie experience at the Music Box Theatre (musicboxtheatre.com). The cinema retains its 1929-era architecture and design, which includes a ceiling of moving clouds and glittering stars. Independent, foreign, and cult films make up many of the 300 screenings the theater hosts each year. In any given month, current releases share billing with ’80s camp classics, mid-century musicals, gothic horror features, and French New Wave flicks. Silent movies are accompanied by a live organ, which also plays at holiday singalongs and weekend intermissions. In addition to two indoor theaters, a cocktail-friendly, 40-seat outdoor viewing area pops up during the summer months.

The Violet Hour
The Violet Hour
Kasama
Kasama
PLAY

In the trendy Wicker Park neighborhood, you can learn the art of making the perfect cocktail with the masters of the craft at The Violet Hour (theviolethour.com). Classes are available during the day and organized by theme: whisky cocktails, Paris in the 1920s, the beauty of amari. During the small-group experience, the bar team will walk you through the hows and whys and set you loose to create two cocktails to imbibe onsite, with a third drink bottled to take away. (Private classes are available as well.) You can also book evening time at the bar (the “front row”) for one or two people and learn to put together a winning old-fashioned or other bartender favorites. Don’t expect to record your visit for posterity (or Instagram), though — cellphones aren’t allowed. To find this speakeasy-style bar, look for the door hidden in a black-and-green mural on Damen Avenue.

EAT

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.

Book Kasama on Resy.

The Beer Temple
The Beer Temple
Aire Ancient Baths
Aire Ancient Baths
DRINK

There are plenty of spots in Chicago where you can enjoy a good glass of beer. The beauty of The Beer Temple (craftbeertemple.com) is that it’s a taproom with an adjacent bottle shop — meaning that if you taste something you like, chances are you can buy some to take with you. Owner Chris Quinn is a certified beer sommelier and a master of beer evaluation (that's an actual title, by the way); in short, he knows his stuff. He curates an interesting, frequently rare, array of 20 diverse drafts from around the world, each one served at either 35°F. or 44°F, depending on what’s optimum for that particular brew. Be on the lookout for a cask ale option as well.

RELAX

Taking inspiration from the spas of long-ago Rome, the candle-lit Aire Ancient Baths (beaire.com) ensures your downtime between meals is truly relaxing. The baths alone are worth the price of admission. For 90 minutes, you can dip and dunk in pools of various temperatures (hot, warm, cold, and ice) and types: a steam bath (the vaporium), a water jet-lined bath (the balneum, aka “Bath of a Thousand Jets”), and a salt bath (the flotarium). To splurge and keep with the food and drink theme, add on the Signature Wine Experience, which draws on the antioxidant properties of red wine grapes to nurture your skin. It includes a 30-minute red wine soak, a cranial massage, and a 60-minute massage, plus access to the baths. Finish your respite with a lounge on the heated marble stones in the relaxation area.

Optimo
Optimo
Monteverde Restaurant & Pastificio
Monteverde Restaurant & Pastificio
PLAY

Shopping is a top Chicago pastime, whether at the big-name luxury stores lining Michigan Avenue, the hip boutiques of Lincoln Park or Wicker Park, or in Andersonville Galleria, filled with items from local makers. For a distinctive souvenir, however, head to Optimo (optimo.com) hatmakers. Its toppers have graced the heads of many a celeb. While you can choose from existing collections filled with fedoras, vaquero-style cowboy hats, Montecristi, and more, a bespoke hat — in a size, shape, and color just for you — is the ultimate in bragging rights. Everything is crafted in Optimo’s workshop, a renovated firehouse on the south side of Chicago, using top-of-the-line felt, straw, ribbon, thread, and other materials.

EAT

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.

Book Monteverde Restaurant & Pastificio on Resy.

Milk Room
Milk Room
Jazz Showcase
Jazz Showcase
DRINK

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.

Book Milk Room on Resy.

RELAX

Chicago has long been synonymous with jazz. And since 1947, the legendary Jazz Showcase (jazzshowcase.com) has been heralding established stars of the genre as well as up-and-comers, offering live music almost every night of the week. Photos and flyers announcing past gigs headlined by jazz greats line the club's walls. But don’t discount the lesser-known acts — you might be lucky and stumble upon the next big thing. Seating is divided between general admission and VIP. Although fans say there’s no bad seat in the house, the upgraded tickets will get you first dibs on the comfier chairs and couches up front.

Must be 21 years of age or older to consume alcoholic beverages. Please drink responsibly.

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