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11 ways to spend Memorial Day weekend in Chicago

Zach Long
Written by
Zach Long

A three-day spring weekend in Chicago means that there's far more than the annual Memorial Day Parade to look forward to. Those sticking around the city will find early-morning bike rides, an outdoor house music dance party, lucha libre wrestling in Pilsen, a circus south of Soldier Field and more interesting events. Check out 11 amazing things to do during Memorial Day weekend that you can try to squeeze in between your cookouts, back porch hangouts and trips to the beach.

RECOMMENDED: Our guide to Memorial Day weekend in Chicago

1. Show off your dance moves on a roller rink

In celebration of its fourth anniversary, Chicago Athletic Association is hosting two Skate Nights this weekend, allowing you to strap on a pair of skates (BYO or rent them for $5) and cruise around its makeshift roller rink in the building's former basketball court. No matter which of the four sessions you choose, you'll be greeted by a DJ spinning tunes and a complimentary cocktail from Apologue Liqueurs.
Chicago Athletic Association. May 24, 25 at 6 and 9pm; $20.

2. Ride your bike on Lake Shore Drive

One of Chicago's most hallowed Memorial Day weekend traditions involves shutting down Lake Shore Drive to traffic and allowing cyclists to take over the scenic road for five hours during Bike the Drive. You'll have to wake up early (the event kicks off at 5:30am) and make sure your ride is tuned up, but experiencing the lakefront in its car-free state is worth the trouble.
Lake Shore Drive from Hollywood Ave to 57th St. May 26 5:30–10:30am; $55.

3. Let someone else man the grill

Looking for something a bit more exciting than burgers and hot dogs on the grill this weekend? At Sunday's edition of the Sportsman’s Club Summer BBQ Series, you'll be able to chow down on dishes cooked by the folks behind Korean/Polish fusion eatery Kimski and contemporary Mexican restaurant Quiote. It's just $20 to join this party (which includes a complimentary beverage).
Sportsman's Club. May 26 at 3pm; $20.

4. Snap an epic selfie

Even if you've already been to wndr museum, you might want to consider a return visit this weekend. At the beginning of May, the exhibition unveiled its second chapter, boasting an array of new experiences such as LED walls that guests can "draw" on with water and an interactive dance station that replicates your moves on a screen. Of course, your journey still ends with a visit to one of Yayoi Kusama's famous Infinity Mirror Rooms.
wndr museum. May 24–27 at various times; $32.

5. Enjoy lucha libre wrestling in Pilsen 

Pilsen's Mole de Mayo street festival may be named for the Mexican delicacy being served by many of the local vendors lining 18th Street, but it's also one of the best places to see lucha libre wrestlers squaring off in the ring. Catch multiple matches during each day of the event, accompanied by live music, an open-air market and lots of delicious food.
18th St and Ashland Ave. May 24, 25 noon–10pm, May 26 noon–9pm; $5 suggested donation.

6. Join a dance party in Millennium Park

The annual Chicago House Music Festival is bigger than ever this year, with sets from legendary local DJ Gene Hunt, London house band Reel People and New York DJ Tony Humphries at Pritzker Pavilion on Saturday (plus footwork DJs and dancing in front of the Bean!). On Friday night, the weekend kicks off with a performances from 8FatFat8 and the duo of Mr Ali and Carla Prather.
Millennium Park. May 24 6:30–9pm, May 25 8am–9pm; free.

7. Hear soulful tributes to historical figures

Local poet and singer-songwriter Jamila Woods headlines a hometown show in support of her sophomore album LEGACY! LEGACY!, which devotes each track to a different artists of color, celebrating the achievements and lessons imparted by figures like Muddy Waters, Betty Davis and James Baldwin.
Thalia Hall. May 26 at 7pm; $31–$66.

8. Ride a Ferris wheel that's not on Navy Pier

Another annual holiday tradition, the Memorial Day Carnival brings all manner of spinning rides and attractions to a parking lot near Lane Tech High School. If you want to see the North Side from atop a Ferris wheel or risk losing your lunch of a Tilt-a-Whirl, this is the place to be.
Lane Tech College Prep High School. May 24 4–10pm, May 25, 26 noon–10pm, May 27 noon–8pm; free, ride passes $25–$30.

9. Take in amazing physical feats beneath a big top tent

Cirque du Soleil's latest touring performance, Volta, attempts to differentiate itself from the Canadian circus company's previous shows, adding BMX bikers, trampoline gymnasts and a pulsating soundtrack (composed by M83 frontman Anthony Gonzalez) to the usual array of trapeze artists, tumblers and dancers.
Soldier Field South Parking Lot. May 24–26 at various times; $49–$245.

10. See one of Shakespeare's strangest plays

Featuring a monologue from the personification of Time and a narrative that balances royal drama with comedic beats in the kingdom's countryside, The Winter’s Tale is one of William Shakespeare's most surreal creations—and the Goodman Theatre's latest staging does it justice.
The Goodman Theatre. May 24–26 at various times; $20–$80.

11. Check out some French masterpieces

The Art Institute of Chicago's latest exhibition “Manet and Modern Beauty” opens this weekend, showcasing French painter Édouard Manet depictions of fashionable women, flowers and fruit. Sure, you could look at photos of stylish debutants (and centerpieces) from the late 1800s, but Manet's impressionist renderings are far more beautiful.
The Art Institute of Chicago. May 26, 27 10:30am–5pm; $7 in addition to regular museum admission.

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