From Al Capone’s old jazz club hang out to freshly baked Swedish pastries
In Solidarity Vibes
The DuSable Museum, founded in 1961 during the Civil Rights Movement, is the oldest independent Black history museum in the nation. The National Museum of Mexican Art in Pilsen is another enlightening museum celebrating Chicago's diversity, and the neighborhood's public art murals are worth discovering, too. Pick up a book for your flight home at Women & Children First, an indie bookstore specializing in feminist and children's literature. Sip the most experimental beers in Chicago at Pilot Project Brewing, a brewery incubator and tasting room that lowers the barrier to entry for indie craft brewers. Get dinner at Wherewithall in Avondale – the four-course, prix fixe menu changes nightly and during the pandemic chef Beverly Kim founded mentorship program The Abundance Setting to help more working moms become executive chefs.
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Old School Vibes
Pay homage to Michael Jordan's GOAT status while snapping a selfie with the statue of Jordan dunking at United Center. The waffle fries and burgers at Bandit are good, but the bathrooms are the real highlight – plastered with collages of Justin Timberlake and Britney Spears bringing 1990s sexy back. Dress the way you did back when those two were still a couple with a vintage outfit from Kokorokoko. Double fist dessert at Pretty Cool Ice Cream, where the colorful ice cream pops make you feel like a kid again. End the evening with a late night jam session at The Green Mill in Uptown, where Billie Holliday used to perform and Al Capone and gang used to hang.
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Playtime Vibes
Stock up on souvenirs and all the toys you need for every kid in your life at Play then try the bumper cars, lacrosse and basketball mash-up that's Whirlyball. Then check out fantastical spray paint animations and step inside a Yayoi Kusama Infinity Room at WNDR Museum in the West Loop before wandering over to Gaijin for Osaka-style okonomiyaki (savory Japanese pancakes) and kakigori shaved ice. Laugh out loud from the front row of an improv show at The Second City, then head upstairs to play super-sized Jenga and Plinko while sipping cocktails at Utopian Tailgate. Save room for cheesecake tic-tac-toe.
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Quiet Energy Vibes
Begin your day with heated vinyasa flow yoga at The Lab Chicago followed by a cup of tea at Fairgrounds Coffee & Tea a few blocks away. It's easy to lose yourself and spend all day at Chuan Spa in The Langham, Chicago. You'll want to arrive early for the bathing ritual, which includes an herbal sauna, aromatherapy shower and heated recliners that will lull you to sleep. Get a simple plant-based, raw meal at Uncooked (the cacio e pepe is outstanding) or opt for a more elegant Michelin-starred meal at Sepia.
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Together Vibes
Start your day with coffee and a cardamom bun or croissant at Lost Larson, a Swedish bakery owned by a talented brother and sister duo. Then, soar high above the skyline with your loved ones for the best views of the city's spectacular architecture with Chicago Helicopter Experience. If you prefer water to the air, paddle the Chicago River with Urban Kayaks. With your feet planted firmly back on the ground, meet the farmers behind Chicago's top restaurants at Green City Market. For dinner, enjoy freshly made pasta and vegetable-forward fare at Daisies, where much of the produce comes from chef Joe Frillman's family farm.
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