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.

By Jennifer Buege

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January 16, 2025

Buckingham Fountain in Grant Park features a tiered central fountain and spouting seal statues. The city skyline is visible beyond.

By Jennifer Buege

January 16, 2025

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 eligible Card Members can enjoy throughout your journey when you book through American Express Travel®.

If you love the arts...

STAY

The bedroom of a Lakeview Suite is decorated with bold yellow patterns and shows off city views with two walls of floor-to-ceiling windows.

Viceroy Chicago

Viceroy Chicago

Entering the Viceroy Chicago is like entering an Art Deco dream. The property’s 1924 brick facade pays tribute to the historic glamour of the surrounding Gold Coast area, though the quaint awning and outdoor seating quickly give way to a newly constructed, 18-story glass structure. The lobby features a 30-foot installation of quotes by Marcel Proust, and the modernist patterns and silhouettes throughout guest rooms help create a stay that’s full of both flair and sophistication. Revel in the throwback décor and classic American eats at Somerset, or venture up to Pandan, the rooftop restaurant, for Southeast Asian fusion and breathtaking views of the city. The hotel is just blocks away from Oak Street Beach, which offers scenic views of Lake Michigan even in colder months, and is also conveniently located near the famed and vibrant Miracle Mile neighborhood.

Gold Card Members have access to the following benefits when booking two nights or more at The Hotel Collection properties like the Viceroy Chicago through American Express Travel.*

12pm check-in, when available

Room upgrade upon arrival, when available**

$100 credit towards eligible charges††

Late check-out, when available

**Certain room categories are not eligible for upgrade.

††Eligible charges vary by property. 

Book Now

PLAY

A white tour boat sails toward the viewer on the Chicago River, having just passed the Reid Murdoch Building and La Salle Street Bridge.

Chicago Architecture Center River Cruise

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

A wide wooden spoon is balanced on a ceramic cup of liquid, holding a multicolored flower of food.

Esmé

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 Now on Tock

RELAX

The marquee of the Music Box Theatre glows with hundreds of tiny lights at dusk. It advertises new and old movies, as well as mini-festivals.

Music Box Theatre

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.

If you travel to eat...

STAY

Elaborately carved dark wood panels frame the Drawing Room, which is filled with books, artwork, and furniture in leather and plaid.

Chicago Athletic Association

Chicago Athletic Association

Once reserved for a list of who’s who, the Chicago Athletic Association is now accessible to anyone looking for a classic yet elegant place to lay their head. The clubby look and feel of the lobby—leather sofas, hand-laid tile, and a trio of fireplaces—sets the scene for your stay. Rooms are bedecked with vintage-style furnishings, such as the pommel horse-inspired ottomans (a nod to the hotel’s sporting past) and brass headboards, as well as modern amenities: Bluetooth speakers (albeit designed to look like old-time radios), rainfall showerheads, and 42-inch flat-screen TVs. While away the time in the Game Room, a bar with bocce, billiards, and other distractions. Inspired by 1950s-era supper clubs, the old-school Cherry Circle Room (bookable through Resy), is the perfect setting to enjoy a martini and bone-in rib-eye. Up high, Cindy’s rooftop setting delivers jaw-dropping views that encourage lingering over lunch, dinner, or drinks.

Gold Card Members have access to the following benefits when booking two nights or more at The Hotel Collection properties like Chicago Athletic Association through American Express Travel.*

12pm check-in, when available

Room upgrade upon arrival, when available**

$100 credit towards eligible charges††

Late check-out, when available

**Certain room categories are not eligible for upgrade.

††Eligible charges vary by property. 

Book Now

PLAY

Detail shot of a bartender’s hand as they pour an amber mixture through a strainer.

The Violet Hour

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

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.

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DRINK

A sign above the store reads “Tap & Bottleshop – The Beer Temple” with hop vines growing through the letters and wheat stalks framing them.

The Beer Temple

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

A dim stone-and-brick hallway leads to a softly glowing pool. Lights on the floor cast patterned shadows on the walls.

Aire Ancient Baths

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.

If you're here for bleisure...

STAY

Cira Mediterranean restaurant is airy, with high ceilings and velvet couches and chairs for seating. A bar on the far wall is well-stocked.

The Hoxton Chicago

The Hoxton Chicago

The Hoxton Chicago lives the story of Fulton Market District in miniature—once industrial, now a hip, creative gathering place attracting locals and business travelers alike. Stop in at Working From_, the on-site coworking space, for high-speed wifi, phone booths for taking calls, and a plethora of snacks and comfy places to work. The property is full of chic eateries for business meals and happy hours, from Lady Bird’s mid-century modern cool in the cellar to the warm wicker and greenery on the rooftop Cabra Cevicheria. When the work day is done, take in some culture at the nearby WNDR Museum, sip a flight at City Winery Chicago, or kick back in the effortless style of your guest room.

Gold Card Members have access to the following benefits when booking two nights or more at The Hotel Collection properties like The Hoxton Chicago through American Express Travel.*

12pm check-in, when available

Room upgrade upon arrival, when available**

$100 credit towards eligible charges††

Late check-out, when available

**Certain room categories are not eligible for upgrade.

††Eligible charges vary by property. 

Book Now

PLAY

Artfully lit fedoras in a range of colors and brim styles line shelves at Optimo.

Optimo

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

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.

Book Now

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.

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RELAX

Saxophonist Anton Schwartz, a white man with dark curly hair, plays on the stage at Jazz Showcase.

Jazz Showcase

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.

Ways to Earn Points with The Gold Card

A Black couple holds hands from separate sun loungers next to a pool framed by lush tropical plants.

The Gold Card offers several Membership Rewards® points-earning opportunities. When you’re ready to travel, you can earn: 3X Points on flights booked directly with airlines or on AmexTravel.com. And 2X Points on prepaid hotels and other eligible travel – such as prepaid car rentals, vacation packages and cruises when you book through AmexTravel.com. Terms apply.

Learn More
A Black couple holds hands from separate sun loungers next to a pool framed by lush tropical plants.

Shop Small® in Chicago

Street view of a lighting store with wide windows showing off lamps and fixtures. The building is blue and a bike is parked out front.

When you Shop Small®, you're not just supporting neighborhood favorites – you're investing in the community. Whether you're a local or visiting, explore our map to find small businesses near you.

View Map
Street view of a lighting store with wide windows showing off lamps and fixtures. The building is blue and a bike is parked out front.

Book Unique Tours & Activities

View from the second seat in a yellow kayak of a woman in yellow paddling. Nearby, two people in a red kayak paddle between cliff faces.

Thrill seekers and adventurers alike can get out and enjoy unforgettable experiences from GetYourGuide booked at gyg.me/amex. Terms apply.

Explore Now
View from the second seat in a yellow kayak of a woman in yellow paddling. Nearby, two people in a red kayak paddle between cliff faces.
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