Skip to consent to cookiesSkip navigation
Mandatory Photo Credit: Abel Arciniega :: @tequilagraphics

Upcoming Chicago Events

Check out what's happening all around Chicago.

Drink the Past Dry
May24
Theatre & Performing Arts

Drink the Past Dry

The nondescript neighborhood bar in the middle of Chicago looks like every other bar in every other neighborhood in the city. A few regulars sit…

Saturday, May 24th
7:30 p.m.9:30 p.m.
Mrs. Murphy & Sons Irish Bistro
3905 N Lincoln Ave
Redtwist Theatre Presents “Gary: A Sequel to Titus Andronicus”
May24
Theatre & Performing Arts

Redtwist Theatre Presents “Gary: A Sequel to Titus Andronicus”

Award-winning Redtwist Theatre, currently presenting, the recently extended through April 6, Titus Andronicus, one of the top rated plays in Chicago, according to TheaterInChicago.com, presents …

Saturday, May 24th
7:30 p.m.9:30 p.m.
Redtwist Theatre
1044 W. Bryn Mawr Ave
Chicago Cop Macbeth
May24
Theatre & Performing Arts

Chicago Cop Macbeth

The Conspirators present Chicago Cop Macbeth by William Shakespeare, adapted and directed by Wm. Bullion, at the Otherworld Theatre, 3914 N. Clark St., May 16…

Saturday, May 24th
8:00 p.m.10:00 p.m.
Otherworld Theatre
3914 N. Clark St.
Here 4 A Bit *Naughty Improv
May24
Music & Comedy, Theatre & Performing Arts

Here 4 A Bit *Naughty Improv

Join us again for a whose line styled night of explosive laughter that will titillate your “funny” bone. Fast paced short form improv, hilarious songs,…

Saturday, May 24th
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
The Antiquities
May24
Theatre & Performing Arts

The Antiquities

A “brilliantly imagined drama” (Wall Street Journal) for anyone whose computer has asked them to prove that they’re a human. Which is to say, everyone.…

Saturday, May 24th
7:30 p.m.9:30 p.m.
Goodman Owen Theatre
170 N. Dearborn, Chicago, IL, 60601
Left Unheard
May24
Theatre & Performing Arts

Left Unheard

Jude has a secret, Ruth has a disability, and Alodia has both. When three siblings reunite, they confront old resentments and new conflicts. What do…

Saturday, May 24th
7:30 p.m.10:00 p.m.
The Theatre School at DePaul University
2350 N. Racine Ave, Chicago, IL, 60614
R.U.R. (Rossum’s Universal Robots)
May24
Theatre & Performing Arts

R.U.R. (Rossum’s Universal Robots)

In 1920, Karel Čapek’s early science fiction classic R.U.R. coined the term “robot” and looked ahead to the wonders and dangers of artificial intelligence decades…

Saturday, May 24th
7:30 p.m.9:30 p.m.
City Lit Theater
1020 W. Bryn Mawr, Chicago, IL, 60660
The Lincoln Lodge
May24
Theatre & Performing Arts

The Lincoln Lodge

The Lincoln Lodge stand-up comedy and variety showcase plays every Friday and Saturday night in Chicago’s glamorous Logan Square! In addition to The Lodge’s rotating…

Saturday, May 24th
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
LET’S PLAY A GAME: Chicago’s scariest short-form show
May24
Music & Comedy, Theatre & Performing Arts

LET’S PLAY A GAME: Chicago’s scariest short-form show

Who’s Line is it Anyways meets Fear Factor in LETS PLAY A GAME, a new short form show that’s a unique blend of comedy, chaos,…

Saturday, May 24th
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Galileo
May24
Theatre & Performing Arts

Galileo

Galileo is a humanizing and compelling portrait of the great scientist, torn between his scientific principles and his desire for the comfortable life that compliance with…

Saturday, May 24th
8:00 p.m.9:30 p.m.
Trap Door Theatre
1655 W. Cortland St.
Paul Simon – A Quiet Celebration Tour
May24
Music & Comedy

Paul Simon – A Quiet Celebration Tour

During “A Quiet Celebration Tour,” Paul Simon will present the live-debut performance of his critically acclaimed, Grammy-nominated album Seven Psalms, as well as perform a…

Saturday, May 24th
8:00 p.m.11:00 p.m.
Chicago Symphony Center
220 S Michigan Ave
Chicago Fireworks Cruise Sail into the Night, with Sparkles in the Sky
May24
Tours & Attractions

Chicago Fireworks Cruise Sail into the Night, with Sparkles in the Sky

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in…

Saturday, May 24th
9:00 p.m.10:30 p.m.
Tall Ship Windy
600 East Grand Avenue Navy Pier
Bright Star
May24
Theatre & Performing Arts

Bright Star

With a Tony-nominated score written by Steve Martin and Edie Brickell, Bright Star follows literary editor Alice Murphy as the introduction of up-and-coming writer Billy Cane leads…

Saturday, May 24th
7:30 p.m.10:00 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
Best Of Annoyance Sketch
May24
Music & Comedy, Theatre & Performing Arts

Best Of Annoyance Sketch

Enjoy the best sketch comedy Chicago has to offer! The Annoyance Theatre has been at the crux of the comedy scene in Chicago for over…

Saturday, May 24th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
ComedySportz Chicago
May24
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Saturday, May 24th
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Chicago Style Improv
May24
Music & Comedy, Theatre & Performing Arts

Chicago Style Improv

Get ready to experience “classic” improvisation that will leave you laughing long after the curtains close! Combining lightning-fast wit, razor-sharp skills, and boundless creativity, Chicago…

Saturday, May 24th
8:00 p.m.9:00 p.m.
The Revival
906 S Wabash Ave
Evanston Salt Costs Climbing
May24
Theatre & Performing Arts

Evanston Salt Costs Climbing

Winters keep getting worse in Evanston, IL, where salt truck drivers Peter and Basil battle the ice and snow and pass the time with jokes…

Saturday, May 24th
8:00 p.m.9:30 p.m.
The Den Theatre
1331 N Milwaukee Ave
AC/DC: Power Up Tour with The Pretty Reckless
May24
Music & Comedy

AC/DC: Power Up Tour with The Pretty Reckless

AC/DC return to the road in the United States for the first time in nine years on the 2025 Power Up North American Tour! Much…

Saturday, May 24th
8:00 p.m.11:00 p.m.
Soldier Field
1410 Special Olympics Dr, Chicago, IL 60605
The Orbit
May24
Music & Comedy, Theatre & Performing Arts

The Orbit

The Orbit is Chicago’s only improv show performed in the round. This 45-minute avant-garde experience takes the audience on a full-circle journey, showcasing a bold…

Saturday, May 24th
11:00 p.m.11:30 p.m.
iO Theater
1501 N. Kingsbury St.
Marriott Theatre Presents: Titanic The Musical
May25
Theatre & Performing Arts

Marriott Theatre Presents: Titanic The Musical

Chicagoland’s longest running musical theatre, Marriott Theatre, continues its 50th Anniversary Season celebration with the epic production of Titanic The Musical, directed and choreographed by…

Sunday, May 25th
Marriott Theatre
10 Marriott Dr.
Franz West: Millennium Park
May25
Museums, Galleries & Exhibitions, Tours & Attractions

Franz West: Millennium Park

Franz West” Millennium Park features two monumental installations by West: Stonehenge (2011) and Dorit (2002), set against the iconic backdrop of Millennium Park. Stonehenge, with…

Sunday, May 25th
Millennium Park
201 E Randolph St
Wolff’s Flea Market Opening Day
May25
Festivals, Fairs & Special Events

Wolff’s Flea Market Opening Day

Wolff’s Flea Market announces opening day April 20, 2025. Join us for our 34th season outdoors at the Allstate Arena, Rosemont. Sundays 6am-2pm through October…

Sunday, May 25th
6:00 a.m.2:00 p.m.
Wolff’s Flea Market
6920 N Mannheim Rd
Teatro Zinzanni
May25
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Sunday, May 25th
5:00 a.m.9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Division Street Farmers Market
May25
Festivals, Fairs & Special Events

Division Street Farmers Market

Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.

Sunday, May 25th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
bean-night

Explore Chicago hotels, flights, deals, and more

Plan your trip

Expedia
Expedia
Expedia
Expedia

CTA Newsletter

Chicago Newsletter

Stay in the know

Sign up

OVG25_enews_cover_for website footer

Chicago Visitors Guide

Start planning today

Get the guide