Chicago
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Chicago is far more than deep-dish and wind chill. Hopscotch the dense clusters of museums, shop hip Wicker Park and keep your head up – the city’s iconic architecture includes works by Frank Lloyd Wright, who started his career here (you can still visit his buildings downtown).
Eat & Drink
Smyth
With two tasting menus – including a one-table-a-night experience where the chefs serve and explain each course – dinner at the two-Michelin-starred Smyth is pricey, but worth the splurge. Husband-and-wife team John and Karen Shields have many ingredients grown specifically for them on a nearby farm, and the resulting dishes, which change daily, are an inventive take on Midwestern fare. Reservations are a must.
Dark Matter Coffee
One of Chicago’s best local coffee roasters, Dark Matter has multiple locations (including one in Avondale, Caravanserai, with Mexican drinking chocolate), but the first location, dubbed the Mothership, is a good place to start. Try barrel-aged coffee, or cool down with an iced Chocolate City coffee, served on draft.
Luella’s Southern Kitchen
Indulge in the comforting flavours of the South at this tiny spot in Lincoln Square, which serves classic dishes like fried chicken, shrimp and grits, and collard greens. With warm hospitality and a laid-back ambiance, Luella’s has become a Windy City icon, and now has a second location within the Time Out Market food hall.
Bagel Miller
Husband-and-wife duo Megan and Dave Miller are well known on the Chicago food scene. They opened Bagel Miller as a pop-up store in 2020 and have been delighting breakfast enthusiasts ever since. Try the pastrami sandwich and the Doughboy Cinnamon, a fluffy brioche-style doughnut rolled in sugar and cinnamon, and take a bag of bagels back home.
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What to Do
Chicago Architecture Center: Art Deco Skyscrapers Tour
A river cruise will show you the sights, but understanding the city’s rich architectural history demands closer attention. This 90-minute walking tour through the Loop includes visits to the lobbies of four art deco landmarks, including the quintessential Chicago Board of Trade building, for a more detail-oriented experience.
Wicker Park
Milwaukee Avenue in Wicker Park is packed with local independent shops, including Una Mae’s (a destination for new and vintage clothing and home decor), Reckless Records and Volumes Bookcafe. Pick up flowers and jewellery at Asrai Garden, or men’s denim at Mildblend Supply Co. Between stops, refuel at Chicago favourite Intelligentsia Coffee.
Garfield Park Conservatory
When Chicagoans need a dose of lushness in the depths of winter, they head to this conservatory – free and open 365 days a year – for lofty spaces filled with palms and ferns (the latter evoking the prehistoric local landscape). Come summer, explore 12 acres of outdoor gardens, including a Play & Grow area designed for kids.
Humboldt House
Claire Tibbs has stocked her sunny shop with finds by Chicago makers, perfect as gifts for others or yourself. Find brass cuffs by Lindsay Lewis, speckled mugs by Commune Pottery and hand-poured scented candles by Tatine Candles. Sister shop Little Peach Fuzz, a block south, features toys and books for kids.
Art Institute of Chicago
With thousands of works of art on display, including Edward Hopper’s Nighthawks and Grant Wood’s American Gothic, two wings and special exhibits, it’s easy to lose yourself here for the day. If you don’t have that long, snag a brochure at the entrance that details how to fit the museum’s highlights within an hour.
Lost Girls Vintage
This funky, brightly coloured shop is a popular haunt for vintage-clothing lovers, whether you’re scouring the city for a Victorian blouse or 1970s glitter dress. Clothing sizes range from 00 to 26 – a partnership with Luvsick Plus, which specializes in vintage for curvy women, means you will find inclusive options on offer.
Unabridged Bookstore
It’s hard to leave this beloved store without a tote full of new books, thanks to personal recommendations from staff (on handwritten notes peppered around the shelves), a featured book of the week highlighting lesser-known writers, and a large selection of marked-down titles.
iO Theater
This comedy club, which also offers improv classes, is the best spot to see up-and-coming acts: Alums include Tina Fey, Amy Poehler and Stephen Colbert. Most shows begin with an audience suggestion, then spiral from there. Grab a drink or snack at the central bar post-show and mingle with the performers.
Independence
Owner George Vlagos stocks indie American brands like Ebbets Field Flannels at this upscale menswear boutique. Sift through vintage finds to snag perfectly worn-in Levi’s, or bring home new shoes by Oak Street Bootmakers, Vlagos’ other endeavour.
The Green Mill
This more-than-century-old jazz club is legendary – Al Capone was a regular – but somehow manages to be non-touristy. Expect a fresh lineup of jazz acts nightly, plus weekly events like open poetry slams. You can catch music until the wee hours most nights (with some shows running until 5 a.m.), so it’s a perfect stop for a lively nightcap.
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