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Photograph: Courtesy CC/Flickr/Ray S

56 exciting openings in May in Chicago

Written by
Nick Kotecki

May is perhaps the most fickle month of spring in Chicago, with days that leap well into the high 70s only to crash into the 40s. So be it. Spend the good days outside at one of the city's best rooftop bars or best outdoor restaurants, and the rest attending the best May 2016 events. When you're not out basking on our favorite Chicago beaches, be sure to keep up with the latest goings on and things to do in Chicago with our complete guide to May's best openings.


Apr 30–May 2: Baconfest is here! Baconfest is here! Sample bacon-infused dishes from a veritable who's-who of Chicago restaurants, including of Black Dog Gelato, Piece, Glazed and Infused, Bang Bang Pie Shop and Taco in a Bag.

May 7: The Polish Constitution Day Parade steps off from a new location this year, marching along State Street from Lake Street to Van Buren Street.

May 8: You love your mom, don't you? Treat the most important woman in your life to the best day ever with our guide to things to do on Mother's Day in Chicago.

May 11–13: The book industry's largest gathering, BookExpo America, holes up in McCormick Place, the largest convention center in America, for three days.

May 13: The Chicago Loop Alliance kicks off one of the coolest parties in town with ACTIVATE, which takes over alleys in the Loop all summer long with live art performances and food and bar service. Save the date(s) because locations are announced only two weeks prior!

May 13–15: The Chicago Department of Cultural Affairs and Special Events taps local entrepreneurs and thought leaders to give talks at the annual Lake FX Summit + Expo.

May 14: For the second year, BookCon brings together authors and readers for Q&A sessions, literary trivia, panel discussions and more. 

May 19: Sip on a nearly unlimited supply of beer from local breweries while in the beautiful confines of the Garfield Park Conservatory at Beer Under Glass.

May 20–22: The biggest anime party in the Midwest is Anime Central, packed with snacks and costumed fans of the Otaku variety.

May 28: Take part in the Memorial Day Parade, which has been a Chicago tradition since 1870.

May 28: Local makers and crafters set up shop in the Plumbers Union Hall for the monthly Randolph Street Market.

May 29: Welcome the start of Memorial Day weekend with one of the most celebrated events in Chicago, Bike the Drive, when Lake Shore Drive is shut down to all traffic that isn't human-powered.

May 30: Another spring, another long Memorial Day weekend. Check out our guide to the veterans' holiday for parades, road trip getaways and more.

Last week of May: Secure your spot in one of Chicago Sport and Social's beach volleyball leagues at your Lake Michigan beach of choice: North Avenue, Oak Street or Montrose.


Apr 28–30: NFL Draft Town returns to Chicago for the second year of possibly many to come.

Apr 30: Chicago Zine Fest brings together makers of DIY publications of all kinds as hundreds fill the Journeyman Plumbers Union Hall.

May 5–7: The newly re-named Off the Trax Music Fest lands in Edison Park with three days of music from more than 45 local and regional bands.

May 7: The colorfully annual (and free!) Kids and Kites Festival floods the sky above Lincoln Park's Cricket Hill with kites and pretty much anything that can float on a string.

May 7: The American Beer Classic has been renamed the Chicago Beer Classic this year, and for good reason—Chicago's local beer makers are getting better and better. Attendees can receive up to 48 two-ounce samples of local and national beers.

May 13: See what the kids are up to in the arts scene at Columbia College's annual Manifest Urban Arts Festival.

May 14: Lincoln Park Zoo's annual fundraiser, Zoo-ologie, helps keep admission free year-round and features close encounters of the animal kind, as well as fair fare and live music.

May 19–29: The Illinois Craft Brewers Guild hosts another Chicago Craft Beer Week at various venues throughout Chicago.

May 20–22: The coming of Mayfest signals the beginning of Chicago's festival season. Hang out in Lakeview in a heated tent while guzzling down local beer and fair-style food.

May 21 & 22: Sample more than 80 wines from all over the world while listening to classical music at the inaugural Lincoln Park Wine Fest

May 21 & 22: Get worldly at the Skokie Festival of Cultures just outside of Chicago and take in all of the ethnic music, dance, food and arts.

May 20–26: The Chicago Critics Film Festival takes over the Music Box Theatre for a movie series handpicked by the Chicago Film Critics Association.

May 20–22: Long Grove Chocolate Fest has local vendors covering tasty treats in chocolate while also serving up live music, beer and brats.

May 28–30: Celebrate the next best thing to St. Patrick's Day in May with Gaelic Park Irish Fest.


May 5: Rick Bayless’s empire grows with Leña Brava and Cruz Blanca, with mescal, tacos and craft beer.

May: Angry Crab, of lowcountry boil fame, will open a second larger location in Wicker Park.

May: Upstairs at the Gwen will serve “elevated libations and bites” above River North.

May: The bar from the group that brought you Tanta, Arbella will open as a “globally minded cocktail lounge."

Mid May: The Hyatt Centric’s rooftop, AIRE, will open, bringing another after-work spot for folks in the Loop.

Note: Restaurant and bar openings are subject to change and can be delayed; call ahead before setting out.


May 3: Soak up the synth-dappeled indie rock of Wild Nothing, which rests somewhere between Philadelphia soul and shoegaze.

May 6: Anything could happen when Ellie Goulding takes the stage at Allstate Arena—we're guessing her glitzy electronica will inspire some dancing.

May 10: Melding R&B and psych-rock, Unknown Mortal Orchestra comes to Thalia Hall with woozy melodies from its latest, Multi-Love.

May 13 & 14: The Punch Brothers throws a progressive hoedown at Thalia Hall, drawing on bluegrass and chamber music influences.

May 15: Zone out to the melancholy arrangements of Swedish prog-rockers Dungen during this intimate performance at the Empty Bottle.

May 15–17: New Wave pioneer Gary Numan turns in a three-night residency at Metro, performing his Replicas, The Pleasure Principle and Telekon albums in full.

May 19 & 20: Texas post-hardcore act At the Drive-In reunites again, taking over the Riviera for two sure-to-be-raucous shows.

May 26–29: More than 100 bands swarm seven stages down south at Summer Camp Music Festival in Three Sisters Park just outside of Peoria.

May 27 & 28: Get in formation and put some hot sauce in your purse as pop superstar Beyoncé brings her stadium tour to Soldier Field.

May 28: Singer-songwriter Damien Jurado plays the science fiction-inspired songs from his latest album, Visions of Us on the Land, at Lincoln Hall.


May 1–Jul 24: See large-format photos taken by Alice Hargrave in "Paradise Wavering," which explores how images can conjure up memories.

May 15–Aug 14: Collage artist (and ornithologist) Tony Fitzpatrick presents "The Secret Birds," a collection of his most recent avian-centric work.

May 22–Aug 13: Inspired by the fabled Chicago Beach Hotel, Karen Reimer creates an ocean out of fabric in her installation "Shoretime Spaceline.”


Apr 27–July 31: Death of a Streetcar Named Virginia Woolf: A Parody is a mash-up of several of the 20th century's most iconic dramas.

Apr 30–Jun 5: The Sign in Sidney Brustein's Window follows a group of intellectuals and activists wrestling with the social movements of the 1960s.

May 12–Jun 12: Charles Newell directs the Midwest premiere of One Man, Two Guvnors, a mod 1960s-set riff on 18th-century farce Servant of Two Masters.


May 11–22: The Joffrey Ballet performs Frederick Ashton's 1948 version of the classic Cinderella story, set to Sergei Prokofiev's score.


May 2–8: The 19th annual Chicago Improv Festival celebrates the art of "yes, and…" with a week of off-the-cuff performances at various venues.

May 23: Adam Sandler and pals David Spade, Nick Swardson and Rob Schneider perform at the Chicago Theatre.

May 17–20: Beloved comedienne and author Carol Burnett takes the Chicago Theatre stage for an evening of memories, audience questions and earlobe tugging.


May 19: Scholars from Northwestern University discuss the development of LGBT hookup culture, from hanky codes to chat rooms to mobile apps in “Looking? The History of Hooking Up.”

May 27–30: Woof your way through a weekend's worth of bear-centric dance parties and other events at the 22nd annual Bear Pride Chicago.

May 27–30: The International Mr. Leather Weekend brings together leather enthusiasts from across the country for a four-day event featuring parties, a fetish and leather market, a physique competition, a sexy shoe-polishing competition and more.

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