Events

The 12 Best Things to Do in Chicago This May

Published On 05/01/2015 Published On 05/01/2015

Date

Event

Location

May 2 Sat

Cinco de Mayo Cantina Crawl Why go to one fiesta on Cinco de Mayo when you can go to five? On this cantina crawl, specialty margaritas flow like the Rio Grande at Municipal Bar + Dining Co., Shay, Epic, Hubbard Inn, and Taco Joint, while mariachi bands and DJs provide a party-hard soundtrack.

River North

Cinco de Mayo Cantina Crawl River North Why go to one fiesta on Cinco de Mayo when you can go to five? On this cantina crawl, specialty margaritas flow like the Rio Grande at Municipal Bar + Dining Co., Shay, Epic, Hubbard Inn, and Taco Joint, while mariachi bands and DJs provide a party-hard soundtrack.

Flickr/Jared Eberhardt

Date

Event

Location

May 3 Sun

Skyline Plunge Benefiting the Respiratory Health Association, the annual Skyline Plunge allows participants to rappel 278ft down the side of theWit Hotel, just like in the skyscraper scene from Mission: Impossible -- Ghost Protocol. Well, almost like it. Kind of. Just, sssshhhhhhh.

theWit Hotel

Skyline Plunge theWit Hotel Benefiting the Respiratory Health Association, the annual Skyline Plunge allows participants to rappel 278ft down the side of theWit Hotel, just like in the skyscraper scene from Mission: Impossible -- Ghost Protocol. Well, almost like it. Kind of. Just, sssshhhhhhh.

Date

Event

Location

May 8 Fri

Point Break, Live! If your girlfriend/boyfriend has been complaining nonstop about how you never see a play together, tell him/her to throw on their finest parachute and strap in for the pedal-to-the-floor stage adaptation of one of the gnarliest movies around, BRAH.

Bottom Lounge

Point Break, Live! Bottom Lounge If your girlfriend/boyfriend has been complaining nonstop about how you never see a play together, tell him/her to throw on their finest parachute and strap in for the pedal-to-the-floor stage adaptation of one of the gnarliest movies around, BRAH.

Flickr/QZAP - Photo archive

Date

Event

Location

May 9 Sat

Chicago Zine Fest If you thought the Internet was weird, wait until you check out the head-spinning array of wacky, hilarious, and bong-brained zines (homemade, pamphlet-like magazines) at this annual fest.

Plumber's Union Hall

Chicago Zine Fest Plumber's Union Hall If you thought the Internet was weird, wait until you check out the head-spinning array of wacky, hilarious, and bong-brained zines (homemade, pamphlet-like magazines) at this annual fest.

Date

Event

Location

May 9 Sat

American Beer Classic What’s more American than drinking a borderline-cartoonish amount of beer at a football stadium? Yeah, nothing. Show Putin how it’s done at the American Beer Classic.

Soldier Field

American Beer Classic Soldier Field What’s more American than drinking a borderline-cartoonish amount of beer at a football stadium? Yeah, nothing. Show Putin how it’s done at the American Beer Classic.

Flickr/Quinn Dombrowski

Date

Event

Location

May 14-24

Chicago Craft Beer Week Prepare your liver for 10 straight days of barley and hops at this boozy version of Chicago Restaurant Week. Beer geeks will take down $4 specialty tastings, tap takeovers, beer dinners, and even live art interpretations of beer/food pairings. With more than 300 venues participating, the event kicks off Thursday with Beer Under Glass at Garfield Park Conservatory.

Multiple locations

Chicago Craft Beer Week Multiple locations Prepare your liver for 10 straight days of barley and hops at this boozy version of Chicago Restaurant Week. Beer geeks will take down $4 specialty tastings, tap takeovers, beer dinners, and even live art interpretations of beer/food pairings. With more than 300 venues participating, the event kicks off Thursday with Beer Under Glass at Garfield Park Conservatory.

Lottie’s Pub

Date

Event

Location

May 16 Sat

Lotties 81st Anniversary Lotties is kind of like your grandma because it’s awesome, has been around forever, and still thinks everything costs 81 cents. Case in point: the bar is offering 81-cent burgers from noon ‘til 4pm and 81-cent drafts all day in celebration of its 81st b-day. Smash the hell out of that piggy bank and get ready to rock.

Lotties Pub

Lotties 81st Anniversary Lotties Pub Lotties is kind of like your grandma because it’s awesome, has been around forever, and still thinks everything costs 81 cents. Case in point: the bar is offering 81-cent burgers from noon ‘til 4pm and 81-cent drafts all day in celebration of its 81st b-day. Smash the hell out of that piggy bank and get ready to rock.

Date

Event

Location

May 19 Tue

Local Option Beer Dinner Part of the Chicago Craft Beer Week festivities, the Local Option Beer Dinner teams up one of the city’s best craft beer bars and most classic restaurants, which in turn go all Captain Planet (and the Planeteers) on your taste buds.

Gino's Brewing Co.

Local Option Beer Dinner Gino's Brewing Co. Part of the Chicago Craft Beer Week festivities, the Local Option Beer Dinner teams up one of the city’s best craft beer bars and most classic restaurants, which in turn go all Captain Planet (and the Planeteers) on your taste buds.

Flickr/Isabelle

Date

Event

Location

May 26-30

The 2nd Annual 26th Annual Comedy Festival With a name like that, you can pretty much tell from outer space that this is an event put on by The Onion. Expect tomfoolery, stand-up comedy by Eric Andre and Kyle Kinane, and wacky film screenings such as Cabin Boy.

Multiple locations

The 2nd Annual 26th Annual Comedy Festival Multiple locations With a name like that, you can pretty much tell from outer space that this is an event put on by The Onion. Expect tomfoolery, stand-up comedy by Eric Andre and Kyle Kinane, and wacky film screenings such as Cabin Boy.

Flickr/Powderphotography

Date

Event

Location

May 28 Thu

Roscoe Village Wine Stroll If there’s one neighborhood in Chicago that would take a wine stroll as seriously as a heart attack, it’s definitely Roscoe Village. So, throw something on with a floral pattern and get ready to sample the hell out of some malbec.

Roscoe Village

Roscoe Village Wine Stroll Roscoe Village If there’s one neighborhood in Chicago that would take a wine stroll as seriously as a heart attack, it’s definitely Roscoe Village. So, throw something on with a floral pattern and get ready to sample the hell out of some malbec.

Date

Event

Location

May 28 Thu

I Sh!t You Not We’re going to give you one chance to guess what the theme of this monthly comedy night is. Hint: it has something to do with pants.

Logan Theatre

I Sh!t You Not Logan Theatre We’re going to give you one chance to guess what the theme of this monthly comedy night is. Hint: it has something to do with pants.

Flickr/lobstar28

Date

Event

Location

May 29-31

Do Division Street Fest Everyone has their favorite Chicago street festival, and Do Division is definitely one of ours. We like to think of it as the unofficial kick-off to summer party season, and its music lineup is more adventurous than most others. This year, throw back a few brewskis while checking out performances by Black Mountain, Tobacco, and Murder by Death.

Wicker Park

Do Division Street Fest Wicker Park Everyone has their favorite Chicago street festival, and Do Division is definitely one of ours. We like to think of it as the unofficial kick-off to summer party season, and its music lineup is more adventurous than most others. This year, throw back a few brewskis while checking out performances by Black Mountain, Tobacco, and Murder by Death.

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