Rose Mary
Touching down in Chicago, the first thing you’ll notice is that the city is drop-dead gorgeous, thanks in no small part to the pristine shores of Lake Michigan butting up against some of the world’s most iconic skyscrapers, and the endless green parks dotting the urban sprawl.
Looks aside, the city’s real heartbeat comes from its inhabitants—a culturally diverse mix who happily stick out the notoriously nasty winters in exchange for some of the best food, architecture, and entertainment in the country. From admiring the city’s concrete masterpieces via boat to treating yourself to Michelin-starred fine dining to catching world-class improv comedy, there’s something for everyone in Chicago.
And no matter where you go, that Midwestern charm is ever present. We’re not just talking about polite strangers here—though you’ll find plenty of those, too–but a metropolitan mood that’s more interesting, flavorful, and welcoming than many of its coastal counterparts. Here are our picks for everywhere to eat, play, and stay in the Windy City.
This sophisticated yet homey Fulton Market restaurant—Top Chef champ Joe Flamm’s hotly anticipated solo debut—pulls in passersby with nautical accents, a roaring open kitchen, and blonde wood furnishings, all inspired by the coastal shores of Italy and Croatia. The menu follows suit, with fresh dishes like zucchini & eggplant tortellini and corn risotto with pickled peppers, which rotate with the seasons.
Courtesy of Rose Mary
Widely recognized as Chicago’s top museum, Grant Park’s Art Institute of Chicago holds an astounding collection of artwork. Built in 1876, AIC is one of the oldest museums in the United States, and the building itself is a precious relic, with magnificent arches preserved from the old Stock Exchange, and two stern bronze lions guarding the entryway. Inside, you’ll find exhibitions spanning every cultural epoch, so whether you appreciate the delicate majesty of a Renoir, gravitate toward stark modern sculpture, or find yourself drawn to the fan-favorite Thorne Miniature Rooms’ meticulously detailed constructions, The Art Institute is sure to impress.
Spend a day wandering the art institute
One of the only boutique hotels on the South Side, this art-strewn, four-star, 98-room recent addition is tucked less than a mile from the University of Chicago, Museum of Science and Industry, and beautiful historical parks like Jackson Park and Midway Plaisance. The rooms are sophisticated and roomy, with unique modern amenities and gorgeous wood flooring. The beach, historic architecture, and tons of restaurants are within walking distance, giving visitors a unique perspective they wouldn’t get staying farther north. Enjoy brunch or dinner at their in-house restaurant, Mesler Kitchen, which offers a crowd-pleasing menu of seasonal American classics.
SOPHY
HOTEL
credits
Established as a bustling publishing house in the 1900s (obviously), this urban bed and breakfast downtown comes with 11 elegantly designed rooms, complete with clawfoot soaking tubs and an abundance of refined details. With plenty of reading nooks throughout, the dining room and living room serve as additional common spaces for relaxing, and the service is friendly and professional.
Publishing house bed & breakfast
The Robey sits in the heart of Wicker Park, a destination for forward-thinking restaurants, trendy cafes, and eclectic shopping from casual vintage to carefully curated boutiques. Stashed inside an art deco landmark building, this repurposed office tower sports opulent lounges plus the rooftop Cabana Club, the perfect place to enjoy a poolside snack while taking in skyline views from atop the standalone tower. The hotel also has lofted rooms inside its Annex building, a renovated adjacent warehouse steeped in urban style, while in-house eatery Cafe Robey serves up elevated local seasonal cuisine below.
THE ROBEY
A wonderfully preserved 1893 Venetian Gothic building houses this luxury boutique four-star hotel. What was once an elite private athletic club is now a renovated landmark where you can enjoy a blend of vintage detail and more modern creature comforts. Beyond its high-end amenities, the hotel occupies prime real estate—perched on Michigan Avenue directly across from downtown’s iconic Millennium Park, it’s also two blocks from Lake Michigan and within walking distance to the Gold Coast. There’s standout food on-site, including the spectacularly scenic Cindy’s Rooftop and the intimate Milk Room.
Chicago athletic association
Preserving trendy Fulton Market’s historically industrial look, the Chicago branch of this Euro import offers sweeping skyline views plus charming rooms with a tasteful mid-century modern aesthetic. No need to venture far from the neighborhood, which is bursting with the city’s top restaurants, shops, and galleries. Or you could always robe up and stay in—the hotel is home to two standout restaurants, including Stephanie Izard’s poolside Peruvian-inspired Cabra on the roof, while in the lobby, Cira serves up a modern take on Mediterranean cuisine.
THE HOXTON
Attracting a laid-back mix of locals and visitors, Big Star’s vibrant Wicker Park homebase has long been a hub for the see-and-be-seen crowd, who come for tasty tacos, nachos, and queso fundido out of a defunct 1940s gas station. The menu is inspired by Mexican street food, and highlights include classic al pastor and barbacoa tacos and chips & guac. As long as it’s warm enough to sit outside without freezing your toes off, expect the sprawling patio to be packed.
BIG STAR
A pioneering operation along Chicago’s Restaurant Row, Girl & the Goat’s chef Stephanie Izard adds her own spin to each of her menu’s rotating global dishes, from shisito peppers with harissa tahini to pork shanks with stone fruit kimchi. Naturally, there’s plenty of goat meat, too, in the form of goat liver mousse and empanadas, among others. The service is far from pretentious yet always exceptional, all delivered within a lofty, elegantly designed room. A broad, open-hearth kitchen spanning the restaurant’s rear adds to the allure.
GIRL & THE GOAT
This approachable yet elevated restaurant serves an upmarket take on Americanized Chinese food. The vibe is sleek and modern, littered with subtle nods to Chinatown staples like vibrant wallpaper, booth seating, and warm vintage lighting. The menu boasts classics like Mongolian beef with crispy cellophane noodles and twice-cooked pork with pickled bok choy, and desserts including housemade almond cookies.
Chef's Special
A standout among Chicago’s deep dish pizza heavy-hitters, this old-school joint serves classic pan-style pizza with a distinctive caramelized crust. The late-night institution has been slinging dough since 1970, and after opening a Lincoln Park location in the 1990s, its loyal following has only grown stronger. Pies arrive in a hot pan laden with perfectly spiced tomato sauce, a surprising layer of cheese stuffed beneath the airy crust, and hearty toppings like sausage, fresh garlic, and fiery giardiniera. In a town saturated with deep dish, this is your ideal introduction.
pequod's
At his long-standing Pilsen taqueria, Mexican-born chef Inocencio Carbajal shares his roots via family recipes and the best Michoacán carnitas in the state (that, unfortunately, routinely sell out in a matter of hours). Everything on the menu is teeming with flavor, with standouts including a chicharrón guisado topped with a mild tomatillo salsa to the carnitas, slow-roasted chunks of pork that are sold both by the pound and taco. Have we mentioned that their tortillas are handmade, too?
CARNITAS
URUAPAN
This no-frills family-run smokeshack will transport you to another era (it opened in 1954) with its prominent neon signage and the mouthwatering scent of smoked meats. It’s the oldest Black-owned barbecue spot in Chicago, and remains the No. 1 destination for all things rib tips and hot links. Lem’s smokes their ribs in an aquarium smoker, a Chicago-style barbecue cooker with glass sliding doors resembling a large fish tank—then, for that extra touch, finishes the racks over a hickory wood fire before finishing it off with a brush of tangy sauce. Don’t skip the Southern sides like creamy coleslaw and homestyle potato salad.
LEM'S BAR-B-Q
Lula brought farm-to-table to buzzy Logan Square before farm-to-table was even a thing. They’ve weathered every storm since, cooking up sophisticated dishes that are as forward-thinking as they are unbound by genre. Open from breakfast (try the brioche French toast) to dinner (the pappardelle with oyster mushroom and walnut bolognese is a highlight), Lula is a reliable source for a delicious meal any time of day.
LULA CAFE
A classic Chicago chophouse with a classy French twist, Bavette’s is the place for a nouveau take on the steakhouse experience. The dimly lit dining room is seductively styled with leather and wood, while the beef, dry-aged and non, is the obvious star of the show. That said, there’s fried chicken and Ōra King salmon for those feeling less carnivorous, along with upmarket sides like truffle mac 'n cheese and Dijon-Parm Brussels sprouts.
BAVETTE'S
Ethiopian-born chef Tigist Reda founded this cozy Uptown outpost, dishing up vibrant dishes informed by her heritage and imbued with rich spices and farm-fresh ingredients. Start with the fried sambusas—pillowy dumplings filled with meat or veggies—before digging into an order of kitfo, Ethiopian-style minced raw beef served with an herbed butter sauce, mitmita seasoning, and side of traditional farmer’s cheese. In typical fashion, main courses are served family-style, featuring a variety of stewed meats, starches, and vegetables plopped atop a round of tangy, spongy injera.
DEMERA
RESTAURANT
Courtesy of Girl & The Goat
Photo Courtesy of Chef's Special, Galdo Photo
Photo by Matt & Sarah Haas
Photo by Matt & Sarah Haas
Photo by Matt & Sarah Haas
Lula Cafe
Courtesy of Bavette's
Courtesy of Demera
Courtesy of Big Star
Opened in 1914, Wrigley Field is home to the world famous Chicago Cubs, and has stood the test of time as one of the most treasured stadiums for America's favorite pastime. The signature coating of ivy along the outfield walls, the makeshift bleachers jutting from the rooftops of neighboring buildings, the original manual scoreboard, and with the contagious energy of the doggedly loyal crowd—it’s tough to resist getting into the spirit of The Show with a Cubbie Dog in hand.
TAKE YOURSELF OUT TO THE BALLGAME AT HISTORIC WRIGLEY FIELD
Chicago’s architecture is among the most jaw-dropping in the country, if not the world, and the best way to discover it is from a comfortable seat smack dab in the middle of the winding Chicago River. Climb aboard one of the First Lady’s many modern rigs and prepare to float along while soaking up everything there is to know about Chicago’s architectural landscape, from art deco and neoclassical to beaux-arts and midcentury modern. Along with a witty sense of humor, the fleet’s trained guides have an encyclopedic knowledge about the structures and their stories.
SNAG A SEAT ON CHICAGO'S FIRST LADY ARCHITECTURE TOUR
Chicago has long been home to energetic stand-up and improv scenes, with all-star homegrown talent like Bill Murray, Amy Poehler, and Jane Lynch, among others. No matter the day of the week, legendary venue Second City offers sketch shows, improv games, and themed events, plus a slew of all-ages and all-levels classes—each of which come with full-belly laughs, promise. Open since the 1950s, the program evolved from a small group of visionary improvers to a comedy powerhouse, playing host to a revolving door of influential comics along the way.
Catch live Chicago-style comedy at Second City
This Ukrainian Village live music venue has been churning out the best of indie rock, metal, rock ‘n' roll, hip-hop, electronic, experimental, punk, jazz, and everything in between since the early 1990s. Its allure lies in the venue’s unbeatable intimacy—a small raised stage creates a personal, unpretentious experience between you and whoever happens to be topping the bill. There’s a pool table and vintage photo booth, only adding to the hole-in-the-wall charm.
POST UP FOR SOME INDIE
MUSIC AT EMPTY BOTTLE
The recently completed Chicago Riverwalk is a 1.2-mile urban pedestrian stretch spanning from Lake Michigan to Lake Street. Meander down the scenic path while admiring rotating art installations along the way. The walk is broken up into four sections—Confluence, Arcade, Civic, and Market—each with their own features, and all with terrific views of the city’s skyline. After a nice jaunt, jump on a boat tour launching from Wacker Drive to see the sights from a different angle.
STROLL ALONG THE RIVERWALK
The namesake of this ethnically diverse westside neighborhood, Humboldt Park sprawls over 200 acres of lush green space and sports a boathouse, the National Museum of Puerto Rican Arts and Culture, a fieldhouse, tennis courts, playgrounds, rentable paddle boats, various ponds, beaches, and fishing areas, wildlife sanctuaries, and a playable replica of Wrigley Field known as “Little Cubs Field." There’s always something going on, from Shakespeare in the Park and live musical performances to film screenings and cultural festivals. Bag up some snacks, drinks, and a blanket, and lose yourself in this little slice of urban wilderness.
PACK A PICNIC FOR HUMBOLDT PARK
This once-abandoned elevated railroad track runs across the northwest side of Logan Square and passes through Humboldt Park, Bucktown, and Wicker Park over its near-three-mile journey. The open-air pathway aimed to convert an underutilized city structure into a green space for Chicagoans to enjoy—an urban park on stilts. The 606 is a fantastic place to break a sweat, and committing to the whole stretch will eventually spit you out at John Walsh Park, a worthy destination in itself.
BIKE, JOg, or walk
the 606
Courtesy of the Art Institute of Chicago
Felix Lipov/Shutterstock
James Andrews/Getty Images
Bruce Leighty/Getty Images
stocklapse/getty Images
Courtesy The Empty Bottle
Courtesy The Second City
Photos by Alan Shortall
Photo by Joshua Haines
Courtesy of Robey
Courtesy of Chicago Athletic Association
Courtesy of Hoxton
Felix Lipov/Shutterstock
First lady
Courtesy The Second City
Courtesy The Empty Bottle
stocklapse/getty Images
Bruce Leighty/Getty Images
Photos by Alan Shortall
Photo by Joshua Haines
Courtesy of Robey
Courtesy of Chicago Athletic Association
Courtesy of Hoxton
FPO
First Lady
Writer: Elanor Bock
Editors: Kelly Dobkin
Editor-in-Chief: Helen Hollyman
Editorial Director: Pete Dombrosky
Photographer: Matt & Sarah Haas
Director of Photography: Drew Swantak
Senior Designers: Grace Han, Maggie Rossetti
Creative Director: Audra V Pace
The flashy Gold Coast neighborhood is known for its high-end retailers, just steps away from even more shopping along Michigan Avenue’s Magnificent Mile. The neighborhood, as its name suggests, is verifiably glitzy, and littered with stunning embellished architecture. Whether maxing out your credit cards or simply window shopping, you’ll find a bounty of luxury boutiques, upmarket showrooms, and designer stores along beautiful Oak Street. On the flipside, longtime hipster enclave Wicker Park hosts a string of outstanding vintage stores, streetwear boutiques, and other casual outposts like Adidas, Toms, and Urban Outfitters, alongside inviting coffee shops, bookshops, and independent restaurants.
Shop for designer duds or vintage finds
Peeter Viisimaa/Getty Images
The flashy Gold Coast neighborhood is known for its high-end retailers, just steps away from even more shopping along Michigan Avenue’s Magnificent Mile. The neighborhood, as its name suggests, is verifiably glitzy, and littered with stunning embellished architecture. Whether maxing out your credit cards or simply window shopping, you’ll find a bounty of luxury boutiques, upmarket showrooms, and designer stores along beautiful Oak Street. On the flipside, longtime hipster enclave Wicker Park hosts a string of outstanding vintage stores, streetwear boutiques, and other casual outposts like Adidas, Toms, and Urban Outfitters, alongside inviting coffee shops, bookshops, and independent restaurants.
Shop for designer duds or vintage finds
Peeter Viisimaa/Getty Images
James Andrews/Getty Images
Wherever you go, your phone goes, so you’ll need on-the-go coverage for all your big adventures. Being America’s leader in 5G coverage, T-Mobile has you covered. In fact, T-Mobile has the most interstate highway miles with 5G (92% coverage to be exact). So go where the open road takes you — and be confident you’ll stay connected to what matters most.
See 5G device, coverage, & access details at T-Mobile.com
COURTESY OF: T-MOBILE
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Wherever you go, your phone goes, so you’ll need on-the-go coverage for all your big adventures. Being America’s leader in 5G coverage, T-Mobile has you covered. In fact, T-Mobile has the most interstate highway miles with 5G (92% coverage to be exact). So go where the open road takes you — and be confident you’ll stay connected to what matters most.
See 5G device, coverage, & access details at T-Mobile.com
COURTESY OF: T-MOBILE
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