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Chicagoist's Guide To May: 20 Fun Things To Do This Month

By Michelle Meywes Kopeny in Arts & Entertainment on May 1, 2017 5:40PM

Bark in the Park is May 21. Image via Bark in the Park's Facebook event page.

Chicago comes alive in May. Here are 20 of our favorite things to do this month to make the most of it.

May 5-6


Attention all indie press and writers, the eighth annual Chicago Zine Fest is this weekend, championing independent self publishing with an exhibition, panels, readings, workshops, hands-on activities and more. The fest kicks off on Friday evening at Co-Prosperity Sphere and then continues on Saturday at Plumbers Union Hall from 11 a.m. to 6 p.m. For the full schedule of events, check the fest website. Free.

Chicago's Leather Archives and Museum. Image via Obscura Day's website.

May 6


Atlas Obscura celebrates discovery and exploration with all kinds of hidden gems and facts, and for one day, they’ll take curious learners with them out into the wild. This Saturday is Obscura Day and Chicago has five events of our very own. Get a private tour of Chicago’s Leather Archives and Museum, explore some of the biggest disasters to shape downtown or have "Breakfast with Tiffany’s...Mosaics." Check out all of the available events and ticketing info on their website.

Kids and Kites Festival. Image via the DCASE Facebook event page.

May 6


The 19th annual Kids and Kites Festival gets at Montrose Harbor gets us outside for a classic springtime activity. The family friendly event will feature the Windjammers Kite Team this year with their synchronized kite flying maneuvers, and the city will provide kite kits to the kids to fly their own. You’ll surely want to stick around for the Big Kite Candy Drop and other activities like face painting, balloon animals and crafts. Free.

Image via Chicago Beer Classic's Facebook page.

May 6


With all the festivals at Soldier Field, drinking on the turf seems like it’s becoming an old pastime. Continue the tradition this weekend with the 5th annual Chicago Beer Classic. There are more than just tastings (from 30+ Chicago breweries) on tap at the beer event. There will be “Beer Education,” games, activities and more, plus extra perks like a stadium tour and premium seating if you splurge for VIP. Two sessions to choose from: 11:30 a.m. or 4:30 p.m. Tickets are $65 ($95 for VIP).

Photo by Quinn B Wharton via Hubbard Street's Facebook page.

May 10-14


Chicago’s top contemporary company Hubbard Street Dance Chicago returns to the Museum of Contemporary Art for danc(e)volve: New Works Festival. The program will feature the latest creations from four Chicago-based choreographers including company member Robyn Mineko Williams and Lucky Plush founder Julia Rhoads. Visit the company’s website for the full schedule of shows. Tickets are $65.

Chicago Farmers Markets. Image courtesy of DCASE.

May 11-November 1


Farmers Markets are back! Chicago’s City Markets open this week across the city and that includes Farmers Markets and other outdoor community markets like Maxwell Street Market. Shop produce, flowers, baked goods and more from regional farmers and growers. The season kicks off on Thursday at Daley Plaza Market where they’ll announce the winners of the 10th Annual Reusable Bag Design Contest and pass out free, reusable bags.

Image courtesy of the Museum of Science and Industry.

May 11-February 4, 2018


The Robot Revolution has arrived. The touring exhibit opens at the Museum of Science and Industry on Thursday and they’ll be showing off how robots can play soccer, make faces and even help in search and rescue efforts. Robots can even fix and repair their own kind in the "RoboGarage." Meet more than 40 robots, including a few new guys like RoboThespian, a life-sized humanoid robot who will greets guests at the entrance, and The Cube Solver, who puts all of us mere humans to shame as he solves a Rubik’s Cube with lightning fast ability. Tickets to Robot Revolution are $12 for adults and $9 for kids in addition to Museum Entry.

May 13-14


The Chicago History Museum kicks off their summer tour series with 24 hours straight of different neighborhood tours. Take in the city’s diverse history during the ChicaGO24 event where you can learn about Logan Square’s street art and graffiti, Gold Coast architecture or the final resting place of city master planner Daniel Burnham in Graceland Cemetery. There are dog friendly walking tours, running tours, even bus, boat and CTA L tours led by curators, historians, authors, artists and other experts. Ticket prices vary by tour. For the full schedule, visit ChicaGO24’s website.

Beer Under Glass. Image courtesy of Garfield Park Conservatory.

May 18


It’s become tradition at Garfield Park Conservatory, celebrating the start of Craft Beer Week and raising funds for the GPCAlliance. The Conservatory’s eight indoor display houses and outside gardens will be open after-hours for Beer Under Glass while guests sip on samples from more than 100 craft breweries. There will also be bites available from local food trucks. General admission begins at 6:30 p.m. Tickets are $60.

May 19-21


Kick off the summer street fest season with Mayfest this weekend at Ashland & Barry Aves. They’ll have food, drink music and fun with popular cover bands playing the main stage and a beer garden under the big-top tent. Admission is $10.

Photo via Chicagoist Flickr pool user Jim Watkins Street Photography

May 20


The Riverwalk has become a hotbed for summer fun since beautification began a few years ago. The Riverwalk Celebration on Saturday will kick off the season’s programming with walking tours from Chicago Architecture Foundation, parades, paddles, puppets and the “Dance of the Bridges.” It all concludes with a pyrotechnic waterfall display. The celebration runs the whole day, from 9 a.m. to 9 p.m. For a full schedule of events, visit the Riverwalk website. Free.

Lincoln Park Wine Fest. Image courtesy of Special Events Management.

May 20-21


Lincoln Park Wine Fest in Jonquil Park boasts two acres for tastings tunes and shopping. Brand ambassadors and sommeliers will be on hand for questions, conversations and food-wine pairings. They’ll also have live music and an open-air market. One-day wine tasting passes are $50. There are also single day VIP passes available for $75 and two-day VIP for $90. For more details on ticketing, visit the fest’s website.

May 20-21


Learn to flip, balance and fly at this year’s Acroyoga Festival at Moonlight Studios. The two-day festival features classes for all levels, whether you’re a pro or have never tried acroyoga. The partner practice combines yoga, acrobatics and therapeutics and encourages community, trust, communication and most importantly, play. Tickets are $95 for one day or $180 for both days. Get 10% off with the code “CHICAGOIST.”

May 21


Oh em gee, it’s a stadium full of dogs. The Anti-Cruelty Society hosts the 23rd annual Bark in the Park in the Soldier Field Stadium Green from 10 a.m. to 2 p.m. Bring your furry friend for the 5K walk, agility course, “pawdicure” spa and shopping at the open air “Barket Place.” Picnics encouraged. Tickets are $40 for adults and $20 for kids. All proceeds benefit The Anti-Cruelty Society.

Jurassic World. Image courtesy of The Field Museum.

May 26-January 7, 2018


This is SUE’s lucky day. The T-Rex’s dreams come true as Jurassic World: The Exhibition comes to life at the Field Museum. The exhibit based on the blockbuster Spielberg film (starring SUE’s celebrity crush, the one and only Jeff Goldblum) shows us what it would be like to walk among living dinosaurs of the prehistoric era. Guests are in for an immersive interactive experience drawn from the real-world science of dinosaur DNA. Tickets are $10 for children and $15 for adults for daytime entry (9 a.m. to 5 p.m.) in addition to general museum admission ($20 for children and $25 for adults for evening entry).

Memorial Day Parade. Image via DCASE's website.

May 27


The City of Chicago’s Memorial Day Parade and Wreath Laying Ceremony begins at 11 a.m. on Daley Plaza honoring fallen heroes and Gold Star family members. The parade will follow at noon and proceed south on State Street. Lt. General Kenneth R. Dahl of the United States Army is this year’s Grand Marshal. Free.

Belmont-Sheffield Music Fest. Image courtesy of Special Events Management.

May 27-28


One of the city’s quintessential street fests, the Belmont-Sheffield Music Fest takes over the streets this weekend with tribute bands, food and libations. It’s the 32nd anniversary for the festival, and this year’s lineup includes Wedding Banned, Boy Band Review, Catfight and more. Entry is a $5 suggested donation benefitting the Central Lakeview Merchants Association.

May 27-28


It’s a weekend full of grapes, gyros and more at the inaugural Greektown Mediterranean Wine Fest in the heart of Greektown. Taste the flavors of the neighborhood’s restaurants and sip on 50 Greek and Mediterranean varietals. Fest hours are Noon to 9 p.m. with ticketed tastings from 2 to 6 p.m. each day. Wine tasting passes are $40.

May 28


Cruising Lake Shore Drive is one of our favorite things to do in the city, and on Sunday the 28th, you can feel the wind in your hair without a car in sight. It’s the annual Bike the Drive event, benefitting the non-profit Active Transportation Alliance and promoting alternative transportation like bicycling, walking and public transit. Beginning at 5:30 a.m. riders will get five hours of car-free time on the drive between Bryn Mawr and 57th Street. Registration is $54 in advance.

Patton Oswalt. Image via the 26th Annual Comedy Festival's website.

May 31-June 4


The Onion’s AV Club is back for their fourth annual 26th Annual Comedy Festival. Patton Oswalt, Mike Judge, Christopher Guest headline the festival that crosses venues around the city for the next five days. Oswalt will be taping a live Netflix special at Lincoln Hall while Music Box Theatre will be screening Idiocracy on 35mm with Mike Judge. Be sure to catch The Adventures of Pete & Pete Reunion and whatever viral weirdness ensues at their very own Clickhole Live! For ticket information and schedule, visit the festival’s website.