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A FASHION Guide to Chicago, the Second City That’s Second to None

Maybe Kim and Kanye should have moved here after all.

According to a study from, over a third of Canadian travellers (38%) plan to take more weekend trips in 2019. If you’re one of those weekend warriors looking for a trip that’s a good time but not a long time (shout out to Trooper), might we suggest…Chicago?

Long known as the Second City, Chicago has undergone a reputation rehab in the past few years – remember those rumours that Kanye West and Kim Kardashian were moving to Chicago full-time? – the city has long been home to some of the continent’s best art, architecture and, believe it or not, shopping. Plus, it’s only an hour and a half flight from Toronto or New York, which makes it the perfect destination for anyone seeking a quick getaway without the burden of jet-lag.

Read on for some of FASHION’s must-sees in the city of Chicago.

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EAT: Portillo’s

Forget Chicago-style deep-dish pizza, Chicago-style hot dogs are arguably the best regional food the city has to offer. Topped kitchen sink style with mustard, relish, onions, a hefty dill pickle spear, tomato wedges and pickled peppers – no ketchup! – the best ones can be found at Portillo’s, a fast-food institution opened in 1963 bearing testimonials from the likes of Guy Fieri on the walls. Open until 1am (at least at the River North location), Portillo’s is packed day and night but entirely worth the wait. Order a slice of the “word-famous” chocolate cake, which owes it’s gooey richness to a dollop of mayonnaise in the recipe.

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Lula Cafe

Located in the heart of leafy Logan Square, Lula Café exudes a ‘locals only’ vibe; every customer looks like they could have played bass in a ‘90s indie rock band, and the servers are the best-dressed art school kids in the city. (I would probably have hit up my server to ask for tips on the best thrift stores in the city, had I not been too embarrassed.) Even if you come for the vibe, stay for the food. They’re one of the original restaurants leading the farm-to-table movement (they’ve been open since 1999!) and serve the best breakfast burritos I’ve ever had in my life.

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SHOP: Asrai Garden

Part flower shop, and part witch’s apothecary, walking into Asrai Garden is like entering a nether realm where everything on offer is just a little bit mystical. Amidst the lush floral arrangements that look like something out of a Dutch still life painting, are taxidermy antelope heads and curiosity cabinets stocked with an array of fine jewellery and healing crystals. It’s the perfect place to pick up a gift for that friend who loves both antiques and astrology.

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A New York Timesarticle from 2009 once called Ikram Goldman’s inimitable boutique, “not so much a temple of high fashion as a pitching ocean liner captained by your favourite eccentric aunt.” Behind a red lacquered façade lies 16,000 square feet of some of the most incredible clothes I’ve ever seen. Since 2002, Ikram has been a pilgrimage site for fashion lovers who flock from all over the Midwest to peep the absolutely breathtaking edit of pieces by Comme des Garcons, Simone Rocha and Maison Rabi Kayrouz. If that’s not enough to convince you, take it from Michelle Obama. The former first lady showed her hometown pride by selecting an angelic white Jason Wu dress from the store to wear to her husband’s first inauguration.

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STAY: St. Clair Hotel

Smack dab in the middle of Chicago’s Magnificent Mile shopping district – and perilously close to a Burberry store – lies the St. Clair Hotel. The beds are uber-comfortable and it was the perfect place to crash after walking all over the city. (It’s only a 15-minute walk to the Art Institute!) Plus, if you’re too tired from all that walking to get dinner, it’s right across the street from local delicacy Garrett Popcorn. (Note: This accommodation was covered by global accommodations leader, where you can find other boutique hotels, rental apartments, and unique property styles.)

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Hotel Felix

A towering painted metal sculpture resembling the Tin Man (perhaps a homage to L. Frank Baum, who wrote The Wizard of Oz while living in Chicago?) guards the entrance to Hotel Felix, suggesting this boutique property skews a bit more bohemian than your average hotel. Inside, the lobby boasts quirky decor such as hanging glass orbs and a wishing well, and happens to smell like recently snuffed candles. The beds are cozy, the staff is kind, and it’s less than a block away from Portillo’s, so get your appetite ready. (Note: This accommodation was covered by global accommodations leader, where you can find other boutique hotels, rental apartments, and unique property styles.)

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VISIT: Wright Around Chicago Tours

Legendary American architect Frank Lloyd Wright spent his formative years in Chicago and left a formidable impact on the city’s architectural history. This bus tour explores his regional legacy beginning at The Rookery, a luxe office building Wright renovated in 1905, then heading to Oak Park, Unity Temple, and is preserved home and studio exist. The daylong tour is perfect for Frank Lloyd Wright disciples, architecture nerds, or history buffs alike (I happen to be all three) – or anyone who just wants to get a good shot for Instagram. (Again, guilty.)

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Quimby’s Bookstore

Quimby’s bookstore rests on founder Steven Svymbersky’s philosophy that, “Everything I like is generally not very popular, and I have to be interested in everything I sell.” According to a generous Google review: “Normal people will find stuff [here] but they will have to look a bit harder.” Indeed, the only words I can conjure to adequately describe Quimby’s are: “freak palace.” Founded in 1991, the bookstore is a hotbed for queer and alternative culture and sells an impressive number of zines, aka self-published pamphlets showcasing their creator’s unique creativity. The Barnes & Noble bestseller table, this is not. In fact, I’d wager there’s nowhere else like Quimby’s in the entire world.