Can’t get out of the city? Never fear: Consider this your go-to guide for getting the most out of the season. As part of our 100 Days of Summer package, we'll be giving you tips on how to have the most fun in the sun in five cities across the country. We’ve already journeyed to New York and Washington D.C., but we certainly can’t skip out on all of the fun there’s to be had in the Windy City.
Plus: Enter to win a four-night trip to Chicago in our current sweepstakes! You'll get two four-day passes to Lollapalooza and a four-night stay at the Kimpton Hotel Monaco, as well as $500 toward your flight and $100 to the South Water Kitchen.
1. Spend the day sunbathing in your favorite bikini at Oak Street Beach. Or, indulge like never before in “Chicago Style” hot dogs and cocktails on the boardwalk. Either way, you’re winning.
2. Score tickets and prepare your festival-wear for the 12th annual Pitchfork Music Festival (July 14-16) featuring over 40 different performers over the course of three days in Union Park, and Lollapalooza, where, in addition to jamming, you can nosh on treats from 34 different food vendors (enter to win tickets here!).
3. Enjoy a free outdoor movie or concert at Chicago’s famous Millennium Park.
4. For the ultimate fun-filled day, head to Navy Pier to ride the Centennial Wheel, check out a public art exhibition (foam, anyone?), or shop your heart out.
5. Cindy’s Rooftop is a must-stop rooftop experience (it’s one of our favorite in the city) for stunning panoramic views and the most picturesque cocktails, entrees, and desserts you’ve ever seen.
6. Load up on fresh produce for summer cookouts and brighten up your space with flowers from Chicago’s beloved farmers markets.
7. Scope out the best paintings, ceramics, photography, and furniture at the Millennium Art Festival. Plus, catch some live performances, good food, and interactive art experiences.
8. Explore the 12-acre Garfield Park Conservatory for a romantic stroll through lush gardens.
9. Discover the city on bike, whether on a leisurely trip down the Chicago Lakefront Trail or a rowdy bike and brewery tour.
10. Spend a sunny day kayaking around the Chicago river and take in the gorgeous skyline view—go the less strenuous route and book one of the famed architecture boat tours.
11. We can’t talk about Chicago without talking about deep-dish pizza. Make it a mission to snag a slice (or an entire pie) at Lou Malnati’s, Giordano’s, and/or Pequod’s.
12. Imbibe to your heart’s content at the Chicago Craft Beer Festival from July 22-23.
13. Try one of everything at Taste of Chicago: a foodie’s dream come true. Deemed the world’s largest food festival, this one definitely deserves a rightful mark on your calendar.
14. Catch a show by The Second City, Chicago’s famed (and seriously hilarious) improv group to scope out the next Tina Fey or Steve Carell.
15. Unwind with a chic picnic full of chilled brews, bite-sized snacks, and Insta-worthy decor by the lake at Promontory Point Park.
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