Sign In
What's On This Month In Chicago | May 2016
Save to wishlist

What's On This Month In Chicago | May 2016

Picture of Culture Trip
Updated: 12 October 2016
While technically May isn’t summer, Chicagoans don’t have to wait to start enjoying warm temperatures outside and all the outdoor programming that comes with it. From the city’s largest beer festival to kite flying, not to mentioned your chance to ride a bicycle down Lake Shore Drive, you’ll have plenty of reasons to be outside this month. On the occasional day the weather is less than stellar? There are legendary musical performances and notable art exhibitions going on as well.


SHOPPING   |   Maxwell Street Market Summer Kickoff

Sun May 1st

Take advantage of the warmer weather while shopping and grooving at the Maxwell Street Market. More details here.


PARADE   |   Cinco de Mayo Parade

Sun May 1st

Start off May on a festive note in the Little Village with the Cinco de Mayo parade. Find details here.


FOOD   |   Tiki Luau at Three Dots and a Dash

Sun May 1st

Three Dots and a Dash is always a cool place for a drink, but their annual luau is even cooler. Find out more here.


FESTIVAL   |   World Fair Trade Day at Daley Plaza

Wed May 4th – Thurs May 5th

Shop and eat with a clear conscience in the middle of downtown for World Fair Trade Day. Click here for more information.


THEATRE   |   Chicago Improv Festival

Mon May 2nd – Sun May 8th

Just when you thought Chicago couldn’t have any more improv shows, the Chicago Improv Festival comes to town. Check for more info here.


ADVENTURE   |   Lincoln Park Zoo Challenge

Fri Mon 6th

Grab some friends and go on a scavenger hunt in a one of kind venue. Find out more here.


FESTIVAL   |   Chicago Kids and Kites Festival

Sat May 7th

There are few family days better than the Chicago Kids and Kites Festival, from kites to face painting and more. Find more information on the event here.


FESTIVAL   |   Chicago Beer Classic

Sat May 7th

Chicago’s largest beer festival is set to open again on the grass of Soldier Field. Find out more information here.



ART   |   Van Gogh’s Bedrooms

closes Tues May 10th

Don’t miss your last chance to see the Art Institute of Chicago’s hit exhibit Van Gogh’s Bedrooms before it’s set to close this month. Find out more here.


SCIENCE   |   Neil deGrasse Tyson at the Chicago Theatre

Tues May 10th

The world’s coolest astrophysicist is coming to Chicago to drop some knowledge. Find details of the event here.


NATURE   |   For the Love of Stars at the 606

Fri May 13th

Want a chance to see the stars without leaving the city? Head to the 606 on the 13th. Find details here.


VOLUNTEER   |   Chicago River Day

Sat May 14th

It’s time to do your part to keep the Chicago River clean and beautiful with this coordinated volunteer effort. Find out how to sign up to help here.


LITERATURE   |   BookCon

Sat May 14th

Bookworms unite for first access to new literature from the industry. Find out more information about the event here.



THEATRE   |   The King and I

closes Sun May 22nd

The Lyric Opera of Chicago’s production of the King and I closes this month. Find more information on this visually stunning show here.


FESTIVAL   |   Chicago Craft Beer Week

Thurs May 19th – Sun May 29th

Chicagoans love their craft beer and this is the beer event to appreciate that fact fully throughout the city. Find out details of events here.


FILM   |   The Chicago Critics Film Festival

Fri May 20th – Thurs May 26th

A curated list of this season’s best festival offerings will be screened this month at the Music Box Theatre. Find details here.


DANCE   |   Counter Balance VII: An Evening of Physically Integrated Dance

Sat May 21st

Chicago’s contemporary dance scene is on full display at this event. Find out more here.


FITNESS   |   Yoga in the Sky at Navy Pier

Sun May 22nd

Do yoga while taking in breathtaking views of the city and lake with this event. Find more information here.



FOOD   |   Pocky Truck

Wed May 11th – Sun Jun 12th

Keep your eyes peeled for a red truck giving out free Pocky around the city. Find out how to find it on purpose here.


ART   |   Invisible Man: Gordon Parks and Ralph Ellison in Harlem

opens Sat May 21st

The Art Institute of Chicago is showcasing the collaboration works of these major cultural figures. Find out more here.


MUSIC   |   Tom Petty at the Riviera Theatre

Sat May 28th

Tom Petty and his band Mudcrutch are coming to Chicago as part of a limited tour. Find out more here.


MUSIC   |   Belmont-Sheffield Music Festival

Sat May 28th – Sun May 29th

You don’t have to wait until the summer to start enjoying the city’s music festivals. Find more information on the festival here.


FITNESS   |   Bike the Drive

Sun May 29th

Once a year bicyclists shut down Lake Shore Drive for a chance to ride the drive in a more relaxed manner. Find more information here.