The My Imperfect Life guide to: Chicago

From martini spots to brunch favorites to classic sightseeing, here's where we love to spend time in Chicago

The best things to do in Chicago, from pizza tours to art museums
(Image credit: Getty Images; Virgin Hotels)

It's no secret: it's a cool time to be Chicago. Whether it's the influence of a certain acclaimed TV show starring a certain Internet boyfriend (hello, Jeremy Allen White) or the fact that, year after year, the Windy City is regularly voted as one of the best big cities on the planet, but Chicago is the big-city cool-kid these days and there's never been a better time to visit. 

From Filipino brunches to boutique hotels, inventive cocktail bars to that impressive skyline, here's your guide on what to see, where to stay and what to do in Chicago, the My Imperfect Life way. 

Top things to do in Chicago: the MIL guide

Stay here: Virgin Hotels Chicago

Its prime location in the Loop in downtown Chicago—right around the corner from the Chicago Theater, mere blocks from Millennium Park and Cloud Gate (a.k.a. The Bean) and less than a five-minute walk to the Chicago Riverfront—might fool you into thinking you that it's a cookie-cutter "tourist area" hotel, devoid of personality or playfulness. 

The Virgin Hotels Chicago proves all of those misconceptions wrong, offering charm, cheekiness and comfort in every corner of its 250-room property, located inside the refurbished Old Dearborn Bank Building on North Wabash Avenue. Guest rooms, called "chambers," feel more like a chic city apartment than nondescript hotel lodging, complete with midcentury-modern furnishings, an ample bathroom with a spacious vanity and dressing quarters, and thoughtful touches like Stelle Bluetooth speakers, yoga mats and a cherry-red Smeg fridge for all of your snack needs. (At press time, the average nightly rate for a base room was $266 per night.) 

Its proximity to downtown means that there are great restaurants, bars and amusements within walking distance but there are also plenty of options directly on the property, from the ground-level Miss Ricky's—serving up diner favorites by day and Italian-accented plates by night—to the rooftop bar Cerise, offering city views and seasonal cocktails from 26 floors up. 

Brunch here: Kasama

You might recognize this laidback bakery–slash–Michelin-starred Filipino restaurant from season two of The Bear, specifically episode three where Ayo Edebiri's Sydney gets to live out all of our dreams and eat her way through Chicago's best restaurants. 

Though Syd being able to waltz straight into Kasama and get a table is an unrealistic bit of TV magic because this acclaimed spot from Timothy Flores and Genie Kwon in Ukrainian Village attracts lines out the door for good reason: the place has some of the best pastries in the country, from black-truffle croissants to buttery Basque cakes flavored with ube and huckleberry, as well as hearty, flavorful Filipino fare, like garlicky rice plates loaded with longanisa sausage or mushroom adobo and crowned with a perfectly runny fried egg. And that inevitable wait in line is made way sweeter with one of Kasama's red-bean cold brews!

Mosey around: The Museum of Contemporary Art Chicago

Chicago is a world-class art town, and its Museum of Contemporary Art is stunning proof. Though the museum's permanent collection is smaller than those found at other local art centers, like the Art Institute of Chicago (another must-visit!), it's MCA's rotating exhibitions that set it apart: past subjects have ranged from iconic British rocker David Bowie to Japanese fine artist Takashi Murakami to Illinois-born fashion god Virgil Abloh. 

As of press time, collections on view include Entre Horizontes, which examines "the artistic genealogies and social justice movements that connect Puerto Rico with Chicago," as well as the early documented performances and video works of British-Palestinian artist Mona Hatoum, 25 years after her first MCA solo show. 

Drink this: A deconstructed martini at Kumiko

Marketed as a "Japanese dining bar," Kumiko's elegant, inventive upgrades to your usual "sip and snack situation" scored the West Loop watering hole a much-deserved spot on the World's 50 Best Bars list. Owner-mixologist Julia Momosé breaks down her cocktail menu into delightfully descriptive categories—think "Provocative and Spiritous" and "Bright, Light and Supple"—one of which is "Component Flights," classic cocktails broken down into their most elemental parts and cleverly updated with Japanese saké. Momosé's crisp, three-part take on an olive martini is just the thing to cut through the kitchen's savory small plates like crispy karaage fried chicken with kanzuri mayo and creamy red-crab croquettes with cabbage salad. 

Instagram this: That riverfront architecture

Chi-town has one of the most famous skylines in the world and the best way to take it all in is via a scenic riverboat tour hosted by the Chicago Architecture Center. Grab a seat aboard the Chicago's First Lady (there's room for 250 passengers across two decks but pro tip, you want a spot up top for the best view!) for a 90-minute open-air rundown of the riverfront's most famous buildings, led by the CAC's expertly trained docents. While there's a daytime tour, the evening cocktail cruise allows you to see the Willis Tower, Old Post Office, Wrigley Building and more bathed in the soft glow of sunset, which would make a gorgeous addition to the grid.

Learn about: Chicago pizza culture

You've definitely heard of Chicago's sauce-drenched deep-dish pizza and you might even be familiar with the city's tavern-style pies, the thin-crust, square-cut rounds originally served in bars after Prohibition. But Pizza City USA, "the only pizza tour in America run by a James Beard Award winner"—food reporter Steve Dolinsky, to be precise—proves that the city actually boasts 10 distinct styles, which you can explore through neighborhood bus tours and pizza walks around areas like West Loop, Wicker Park and Bucktown. Each tour includes pizza tastings, obviously, but also kitchen tours, expert analysis and more, so come hungry and ready with all of your 'za-related questions!

Shop here: Lindsay Lewis

Take a piece of your Second City trip home with you with a lovely, locally-made piece of jewerly from Chicago-based designer Lindsay Lewis. Her handmade pieces—which include dangling double-strung earrings, delicate chain necklages and decorative cigar-band ring—modern, minimalist but with architectural intrigue to have onlookers questioning, "Hey, where did you get that?" You can check out the goods for yourself at the designer's studio and showroom at 2712 W North Avenue in Logan Square by appointment on Tuesdays through Thursdays from 3pm to 6:30pm. 

Don't miss: Garfield Park Conservatory

We always love a bit of greenery in our travels, especially in otherwise urban locales like Chicago, and Garfield Park Conservatory is a plant parent's wet dream. One of the largest botanical conservatories in the nation, the green space features thousands of plant species from around the world in its landmark field house, indoor display gardens (such as the tropical Palm Room and the cacti-filled Desert House) and sprawling park grounds, complete with lagoons, lily pools and flower gardens. And adding even more peacefulness to the place, the conservatory also hosts painting workshops, yoga sessions, beekeeping classics, origami open houses and more. 

Want even more travel recommendations? Check out our destination guides to New York City, Lisbon and the Amalfi Coast

Christina Izzo

Christina Izzo is the Deputy Editor of My Imperfect Life. 

More generally, she is a writer-editor covering food and drink, travel, lifestyle and culture in New York City. She was previously the Features Editor at Rachael Ray In Season and Reveal, as well as the Food & Drink Editor and chief restaurant critic at Time Out New York

When she’s not doing all that, she can probably be found eating cheese somewhere.