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The best of what to do in Chicago this month

The sun’s out in the Windy City, so get outside! There will be unbelievable kite-flying performances at Cricket Hill’s Kids and Kites Festival, and Jonquil Park will become a tranquil vineyard for a weekend at the Lincoln Park Wine Fest. Get up early to bike scenic Lake Shore Drive, which is closed to cars for a few hours in the name of charity.

AFAR Local is our monthly insider guide to the best of what’s happening in cities around the U.S.

May 6 | Drink
Chicago Beer Classic
You may have sipped a beer in the stands of Soldier Field, but have you sipped one on the grass? At the Chicago Beer Classic, you can do just that. A ticket to the event includes 48 two-ounce beer samples, and with 100 breweries represented on the Chicago Bears’ front lawn, you won’t be lacking in options. There will also be food and entertainment and, if you spring for VIP, a tour of the field, among other bonus goodies.
11:30 AM | 1410 S. Museum Campus Dr., Chicago | From $60 | website

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May 6 | Outdoors
Kids and Kites Festival
The wind in the Windy City is picking up this time of year, which makes for perfect kite-flying weather. The Kids and Kites Festival takes advantage of the season with high-flying performances courtesy of kite professionals such as the Windjammers International Kite Team, known for their eerily synchronized flying moves. The fest also hosts the Big Kite Candy Drop—basically a piñata in the sky—and child and adult amateurs and professionals alike can use the open sky to practice their own kite skills.
10:00 AM - 4:00 PM | Cricket Hill, West Montrose Dr. between Montrose and Wilson Aves., Chicago | Free | website

May 10 - 14 | Dance
Hubbard Street’s Danc(E)volve: New Works Festival
Chicago’s Hubbard Street dancers are returning to the Museum of Contemporary Art for their annual Danc(E)volve event. Catch the contemporary dance troupe performing four choreographies, including two world premieres, ideated by the award-winning choreographers Robyn Mineko Williams and Penny Saunders, Chicago-based Julia Rhoads, and Hubbard Street veteran Alice Klock.
Museum of Contemporary Art, 220 E. Chicago Ave., Chicago | $65 | website

May 17 | Music
Barry Manilow
No matter your age, it’s hard not have a good time to the soundtrack of Barry Manilow’s smooth contemporary. (Just try to keep from singing along to the chorus of “Copacabana”—we dare you.) He’s currently on a tour of Chicago, New York, and Los Angeles, performing songs from his new album along with all his hits, such as “I Write the Songs” and “Looks Like We Made It.”
7:30 PM | Allstate Arena, 6920 N. Mannheim Rd., Rosemont | From $37 | website

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May 20 - 21 | Drink
Lincoln Park Wine Fest
The trendy Northside neighborhood will be transformed into a two-acre wine mecca for a weekend during the Lincoln Park Wine Fest, an annual event where you can sip local and international wines, snack on artisan eats, and discover the best pairings of the two. Your admission ticket buys you 12 tastings with options ranging from bottles of Argentinian malbec to Californian cabernet. Don’t want to drink? Buy a designated driver ticket for only $20 and get access to the event sans tastings.
12:00 PM - 4:00 PM | Jonquil Park, 1001 W. Wrightwood Ave., Chicago | From $50 | website

Chicago Beer Classic

May 26 - 28 | Entertainment
Chicago Watch
If you’re a fan of any of NBC’s Chicago-based dramas, including Chicago Fire, Chicago PD, Chicago Med, and Chicago Justice, or just a crime drama fan in general, then you’ll be among like-minded folks at Chicago Watch. The event brings the stars of these television shows (Taylor Kinney, Torrey DeVitto, and Gregg Henry, to name a few) out for photo ops, autographs, Q&A panels, plus trivia and other games. This is the first of what’s expected to become an annual event, so now’s your chance to say you knew about it first.
Hyatt Regency McCormick Place, 2233 S. Martin Luther King Dr., Chicago | From $45 | website

May 27 | Parade
Chicago Memorial Day Parade
Chicago doesn’t skimp when it comes to parades: Some of the biggest ones in the country are held right here in the Windy City. Memorial Day is no exception. The annual event has been running since 1870, and plenty of people come out to watch the march of politicians, veterans, marching bands, and decked-out floats. Get there early to snag a front-row seat along the route, and bring a lawn chair if you really want to settle in comfortably.
12:00 PM | State St. from Lake to Van Buren Sts., Chicago | Free | website

May 27 - 28 | Music festival
Belmont-Sheffield Music Festival
A Memorial Day Weekend tradition for over 30 years, the Belmont-Sheffield Music Festival highlights the city’s best homegrown tribute bands, from the Led Zeppelin–honoring band Kashmir to genre- and generation-spanning cover band Rod Tuffcurls and the Bench Press. Plus, the festival is located within walking distance of the Belmont Red Line, making transportation a no-brainer.
12:00 PM - 10:00 PM | 3200 N. Sheffield Ave., Chicago | $5 | website

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May 28 | Outdoors
Bike the Drive
On just one day a year, the city closes the entirety of Lake Shore Drive, a scenic highway that runs along Lake Michigan. For five hours in the early morning, no cars will be allowed, but cyclists of all levels and ages are welcome to bike the route as the sun comes up. Your ticket to this breathtaking ride is attractive for another reason, too: All proceeds from the event go to benefit the Active Transportation Alliance, which is constantly working to improve biking trails, walking paths, and public transit throughout the city.
5:30 AM | Multiple starting points along Lake Shore Dr., Chicago | From $17 | website

June 17 | Book ahead: Music
Aretha Franklin
We don’t have to tell you that Aretha Franklin’s performance at the Ravinia Festival will sell out fast. Snag tickets ASAP so you’re not left wishing you were headed to hear live versions of “Chain of Fools,” “(You Make Me Feel Like) A Natural Woman,” and “Respect.” While you’re at it, consider checking out some of the other concerts during Highland Park’s Ravinia Fest—One Republic, the Beach Boys, Andrew Bird, and Stevie Nicks are just a few of the musicians gracing the fest’s multi-month lineup.
8:30 PM | 200 Ravinia Park Rd., Highland Park | From $38 | website

Danielle Braff lives in Chicago with her husband, two daughters, two cats, and her dog. When she’s not writing, she’s out photographing her city and running around frantically trying to fit as many events as she can into her day. You can check out her other articles at Daniellebraff.com.

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