Seven Cool Things to Do on a Warm Weekend in Chicago

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Chicago winters ain’t nothing easy. Cold air and wind that goes right through you, months of overcast skies—not ideal conditions!

But that all changes once things warm up. Once you’re past a dead-cold winter and a spring that doesn’t quite hit, outside gets warm enough to enjoy fully. It’s an energy you can feel throughout the city, which is why its summers are so famous. The nice weather lets you enjoy Chicago’s fantastic food scene, lovely lake beaches, and a joyful, dynamic culture with the grit you expect from a city, minus the gruffness. Midwestern friendliness is strong here, so you’ll catch a vibe if you go with a crew or venture out solo.

If you’re venturing out to Chicago this summer, here are seven cool things to check out while you’re there.


Art Institute of Chicago

Almost anyone will tell you to check out the Art Institute of Chicago, as it is home to some of the country’s finest art collections. It’s always worth a visit, whether or not you actually paid attention in art history class. Through its labyrinth halls, you’ll find works from Van Gogh, Diego Rivera, Georgia O’Keefe, and many more. Have your Ferris Bueller moment in front of Georges Seurat’s iconic pointillism masterpiece, A Sunday Afternoon on the Island of La Grande Jatte. Imagine yourself in a smoky 1940s nightclub, the air spiced with the aroma of rum and whiskey, twirling with a well-dressed partner to a live jazz band as you view Archibald John Motley Jr.’s Nightlife.

Special exhibits open right now and to come include Salvador Dalí: The Image Disappears (Feb 18-Jun 12),  Gio Swaby: Fresh Up (Apr 8-Jul 3), Kwame Brathwaite: Things Well Worth Waiting For (Feb 25-Jul 24), and Van Gogh and the Avant-Garde: The Modern Landscape.


Garfield Park Conservatory


Exploring nature at summer camp

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An afternoon walking amongst plants is an afternoon well spent. Head over to the Garfield Park Conservatory and wander through 12 acres of gardens (10 outdoor, two indoor), which house several species of plants that grow in all different climates and landscapes. Visit the Conservatory’s Desert House and peruse its collection of succulents. Walk over to the Fern Room and get a feel of Chicago—millions of years ago. The Conservatory’s largest room, the Palm House, is a 65-foot high enclosure laden with palms, as well as plants and animals that feel right at home in warm places. 

When you’re done exploring the sunning enclosures, you can tour through the Conservatory’s 10 acres of outdoor gardens, including an art garden and a demonstration garden where you can get some tips on how to sustain your plant life.


Vintage Shopping + Mexican Brunch in Pilsen

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There’s a lovely little afternoon to be had in Pilsen if preloved threads are your thing. The Lower West Side Neighborhood is eclectic, and on its 18th Street strip, you’ll find several vintage clothing stores with selections that make it impossible not to find something suitable for a major steal. There are several spots to explore, but make sure you stop in at Trash (lots of cool well-priced T-shirts), Knee Deep Vintage, and Pilsen Vintage, where you can find some truly stunning and unique pieces tucked away in its racks.

When you’re done shopping, hop into Azul 18 for its delicious fusion of American and Mexican cuisine, done with an obvious appreciation and deep understanding of both. Trust, whatever you have will be delicious.


Gangster Tour

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Chicago’s a pretty exciting history of mobsters (the name Al Capone rings any bells?). Several tours highlight these notorious troublemakers and how their deeds influenced the city’s history and culture.

If you’re craving something more spooky, you can also find haunted tours that touch on the metaphysical consequences of these gangsters’ exploits.


Frank Lloyd Wright Trust


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An architect’s dream home: Frank Lloyd Wright’s two-story residence. Wright is responsible for some of Chicago’s historic buildings, like the Unity Temple in Oak Park and the Rookery, which you’ll find in the city’s financial district.

Wright’s prairie-style homes, which he built near the beginning of the 20th Century, are stunning examples of American architecture. You’ll find many of them in Oak Park, where he built his family home where he was allowed to flex his creativity and artistry fully. Stop in to see its stunning murals, skylights, ceilings, and spaces.


Morton Arboretum

fall romantic getaway

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Where would we be without trees? The folks at the Morton Arboretum want you to remember how crucial these plants are to our survival. Walk through its gardens, take a birdwatching class, do a wine tasting, see an outdoor exhibition, and bike through the ground—all against a verdant midwestern backdrop. It’s a great place to spend a warm afternoon and a nice little respite from the city landscape.


Visit a beach

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Chicago’s beaches are probably its summer’s best feature. Located all around Lake Michigan, the city has about 26 miles of lakefront, and they come alive once it gets warm enough. Montrose, Oak Street, North Avenue, and South Shore beaches have dining options with a water view. 31st st beach has beautiful views of the Chicago Skyline, Foster Beach is great for families, and Hollywood Beach is very LGBTQ-friendly.