The Perfect Three Days in Chicago

Mixing big city vibes with Midwest charm, Chicago combines luxury shopping and Michelin-starred dining with wide open nature spaces and the kind of hospitality where no smile is forced. We've created the perfect three days in the Windy City where you can experience the best this lakeside metro has to offer.

Breakfast at Kasama

Kasama is one of those places that just stays with you. As the first Filipino restaurant in the world to earn a Michelin Star, it’s a true love letter to the community—so much so that we’ve heard people get emotional over their meals. In the morning, it’s all about the pastry case—think perfect kouign-amanns and longanisa egg sandwiches—but if you can, come back for the 13-course tasting menu. Wagyu bistek, caviar-topped kinilaw, and the most delicate lumpia—its Filipino flavors elevated in a way that still feels deeply personal. Just be prepared to wait for breakfast as the line can stretch for 45 minutes, but trust us, it’s worth it.

Shopping at Ikram (Along Magnificent Mile)

Ikram—named after owner Ikram Goldman—is a must; the offering is as bold and impeccably curated as its namesake. Every piece in the shop feels intentional—she only sells what she truly loves, and you can feel that passion the moment you walk in. We also love wandering down Magnificent Mile to hit up spots like Ralph Lauren, Notre, and Space 519 for a mix of timeless and unexpected.

Check Out at AIRE Ancient Baths

Tucked inside a restored 1902 factory, AIRE is all moody brick, flickering candlelight, and thermal pools that make you feel like you’ve stepped into another era. It’s 18 and over, which keeps the vibes in check, and whether you’re floating between the different baths or indulging in a massage with their signature Orange Garden oil, you leave feeling completely renewed. Reservations are a must—it books up fast—but it’s absolutely worth planning ahead for.

Dinner at Oriole

This place reminds you why tasting menus are worth the splurge. Chef Noah Sandoval makes every course feel like a revelation. The wine pairings are lovely, but if you’re skipping alcohol, the spirit-free pairings are just as thoughtful. If you can, book the kitchen table—it’s the best seat in the house: you get a front-row view of the magic happening behind the scenes.

Morning at the Lincoln Park Zoo

This Zoo, like so many of the biggies, is a treasured Chicago landmark. And you don’t have to be a kid to enjoy it. There are over 200 animals, from tiny pygmy hippos to giant African lions and endangered black eastern rhinos. Admission is always free, though you should check the site ahead of time for a list of special exhibits. Think of it as a particularly eventful walk in the park, and know you’re supporting the zoo’s conservation and animal welfare efforts.

Lunch at Le Colonial

At Le Colonial, visit 1920s Saigon via modern-day Chicago. Right above the Gold Coast is where you go for refined Vietnamese cuisine–crispy spring rolls, shaken beef, Thai chili Margaritas–with a side of tropical wallpaper and more charm than you’ll find in all of Paris.

Dinner at Tre Dita

Make your way to Tre Dita for Italian done right, or rather, done Chef Evan Funke’s way, ie. masterfully. Conveniently situated inside the St. Regis, it’s got soaring 40-foot windows framing Chicago’s skyline and a menu that’s all handmade pasta, wood-fired meats, and a perfectly seasoned bistecca. Reservations are required, but you might have luck at the bar, where you can get a taste of whatever you’re craving with a negroni (or a selection from their 400-bottle spirits collection) in hand.

Cocktails at The Pearl Club

End your evening on an unapologetically opulent note, draped in deep blue velvet and gilded details, at The Pearl Club. The small bites are decadent (wagyu pigs in a blanket are a revelation), but the cocktails are the show-stoppers here. Their signature drink, The Pearl—Cucumber Sneaky Fox Vodka, Aelred Melon, and Chareau—is a safe order if you’re looking to try something new. Reservations are encouraged, but you should still try your luck if it’s a last-minute decision.

Brunch at Lula Cafe

Ease into the day at Lula Cafe, the heart and soul of Logan Square. Since 1999, this neighborhood staple has been churning out seasonal dishes so good they’ve been written up in The New York Times, Food & Wine, and Bon Appétit. With a James Beard Award for Best Hospitality under its belt, Lula is a just as good at atmosphere as it is at food. Grab a seat on the patio or at the counter and dig into their legendary brunch—perhaps a sweet and savory strata or their local-beloved breakfast burrito.

Architecture Boat Tour on the Chicago River

Chicago’s First Lady cruise is for a front-row seat to the city’s legendary skyline. As the official river cruise of the Chicago Architecture Foundation, this tour is equal parts luxury and education. With a full bar, plush seating, and an open-air upper deck, it’s a stylish way to take in the soaring skyscrapers while expert docents share the stories behind the city’s most iconic buildings.

Stroll the Riverwalk

Once back on land, take a sunset stroll along the Chicago Riverwalk, where the city’s past and present converge in a dazzling urban escape. Explore the McCormick Bridgehouse & Chicago River Museum to see the inner workings of the city's famous bridges, or simply soak in the atmosphere of waterfront dining, kayak rentals, and open-air bars. As dusk falls, don’t miss Art on the Mart, a breathtaking digital projection that transforms the massive Merchandise Mart into a living, ever-changing canvas of contemporary art.

Dinner at Kumiko

After a day of exploring, settle in at Kumiko—it’s going to be a fun night. This is a sort of refined restaurant-slash-bar where the experience is as much about the drinks as it is about the food. The operation is led by Julia Momosé, a recipient of Michelin’s Exceptional Cocktails Award, while the space subscribes to a refreshingly understated ethos. Opt for the seasonal tasting menu to experience the full harmony of Japanese technique and world-class spirits, or graze à la carte on small plates and cocktails.

Jazz at The Green Mill

End the night at The Green Mill, a jazz club with a past as smoky and sultry as its music. Once a speakeasy under the control of Al Capone’s crew, this legendary haunt is steeped in Prohibition-era lore. Slip into a velvet booth, order an old-fashioned, and let the live jazz transport you to another time. Whether you’re here for the music, the history, or just the perfectly dim lighting, The Green Mill is a Chicago experience that lingers long after the last note fades.

Hotels We Love: The St. Regis

Nightly Champagne sabering is one of the many moments that prove The St. Regis Chicago is all luxury, all the time—and Shrtlst members (that’s you) get all the Virtuoso perks, too: upgrades, daily breakfast, a $100 credit, and more.

Wishi Styles Chicago: The Windy City Edition

We asked our friends at Wishi to put together the perfect Windy City look, complete with pile-on-or-peel-off layers that'll keep you comfortable in the shifting Chicago weather this spring. As a Shrtlst member, you get 30% off all Wishi styling services, plus access to destination-specific inspirations like this one.

Itinerary Curator:

Meet Kate. Being that she started out under the legendary Chef Nancy Silverton and weaved her way through L.A. and Chicago’s world-class food and wine circles, KG, as we lovingly call her, knows how to craft a worthy experience. Curating unforgettable events, pairing wine with vinyl records, or something else entirely—her taste is impeccable.

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