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

Upcoming Chicago Events

Check out what's happening all around Chicago.

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
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.
Fleurs de Villes Downton Abbey
May25
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Tours & Attractions

Fleurs de Villes Downton Abbey

Fusing floral design and bespoke fashion, global sensation Fleurs de Villes returns to 900 North Michigan Shops May 21-25 with new show Fleurs de Villes Downton Abbey – a fresh…

Sunday, May 25th
11:00 a.m.6:00 p.m.
900 North Michigan Shops
900 North Michigan Avenue
Sunday Funday Lake Cruise
May25
Festivals, Fairs & Special Events

Sunday Funday Lake Cruise

🚨 Sunday Funday Alert! 🚨 Bloody Mary Fest & Chicago Social Presents: A Sunday Funday Lake Cruise 🗓 Sunday, May 25 | ⏰ 12:30PM –…

Sunday, May 25th
12:30 p.m.2:00 p.m.
Island Party Boat
355 East Riverwalk South
Ravensburger Puzzle Race – Snakes & Lattes Chicago
May25
Festivals, Fairs & Special Events

Ravensburger Puzzle Race – Snakes & Lattes Chicago

Compete for prizes! Come and try to win the puzzle contest with your friends! Join us every second Sunday of the month from 3PM to…

Sunday, May 25th
3:00 p.m.5:00 p.m.
Snakes & Lattes Chicago
1965 N. Milwaukee Avenue
Every Brilliant Thing
May25
Music & Comedy, Theatre & Performing Arts

Every Brilliant Thing

CIRCA Pintig, Chicago’s Filipino American theatre company in its 34th year, presents EVERY BRILLIANT THING, the groundbreaking one-performer play written by Duncan Macmillan with Jonny Donahue.…

Sunday, May 25th
7:00 p.m.8:30 p.m.
1332 W Irving Park Rd, Chicago, IL 60613
1332 W Irving Park Rd
Rockin’ in the Park 2025 Free Summer Concert Series
May25
Music & Comedy

Rockin’ in the Park 2025 Free Summer Concert Series

Rosemont’s Parkway Bank Park entertainment district (5501 Park Place, Rosemont) will turn up the volume this summer with the return of its popular “Rockin’ in…

Sunday, May 25th
7:00 p.m.10:00 p.m.
Parkway Bank Park Entertainment District
5501 Park Place
Division Street Farmers Market
May26
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.

Monday, May 26th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Board Game Designer Night – Snakes & Lattes Chicago
May26
Festivals, Fairs & Special Events

Board Game Designer Night – Snakes & Lattes Chicago

Join us at Snakes & Lattes Chicago for our Board Game Designer Night, hosted every month twice. Interested in game design? Have board game ideas? Want to playtest…

Monday, May 26th
6:00 p.m.10:00 p.m.
Snakes & Lattes Chicago
1965 N. Milwaukee Avenue
Late Nite Mic with Vik Pandya at The Comedy Bar
May26
Music & Comedy

Late Nite Mic with Vik Pandya at The Comedy Bar

IMPORTANT HOUSE POLICIES: PLEASE READ 📍 All shows take place at 162 E Superior St. – The entrance to the venue is on Superior Street, just east of the…

Monday, May 26th
7:30 p.m.9:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Division Street Farmers Market
May27
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.

Tuesday, May 27th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
The Farmer at The Green
May27
Festivals, Fairs & Special Events

The Farmer at The Green

The Farmer at The Green, presented by BMO, is a downtown Chicago farmers market. Shop for fresh, seasonal produce and locally made products from Chicago-based…

Tuesday, May 27th
11:00 a.m.3:00 p.m.
The Green at 320
320 S. Canal St.
Tuesday Good Show
May27
Music & Comedy

Tuesday Good Show

Showcasing some of the best performers in the city, Tuesday Good Show is a free weekly variety show hosted by Nick Bonsignore and Keller Paulson.…

Tuesday, May 27th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Tomato Throw Show at The Comedy Bar
May27
Music & Comedy

Tomato Throw Show at The Comedy Bar

Join us for the most fun interactive comedy show in Chicago, where the audience determines who’s the funniest (and the most unfunny) by throwing [fake]…

Tuesday, May 27th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Comic Court: The Best Comedy Show in the World
May27
Music & Comedy, Theatre & Performing Arts

Comic Court: The Best Comedy Show in the World

Would you rather be able to fly or be able to turn invisible? Who are we more tired of: Ryan Reynolds or Dwayne Johnson? Would…

Tuesday, May 27th
9:00 p.m.10:30 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
Division Street Farmers Market
May28
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.

Wednesday, May 28th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Dame Myra Hess Memorial Concerts | Johannes Gray, Cello and Anastasiya Magamedova, Piano
May28
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Dame Myra Hess Memorial Concerts | Johannes Gray, Cello and Anastasiya Magamedova, Piano

DAME MYRA HESS MEMORIAL CONCERTS | JOHANNES GRAY, CELLO ANASTASIYA MAGAMEDOVA, PIANO  Program Jean Sibelius – Malinconia, Op. 20 Felix Mendelssohn – Cello Sonata No.…

Wednesday, May 28th
12:15 p.m.1:00 p.m.
Seventeenth Church of Christ, Scientist, Chicago
55 E. Wacker Drive
Joe Fenti at The Comedy Bar
May28
Music & Comedy

Joe Fenti at The Comedy Bar

Joe Fenti is a Boston-based comedian who sometimes makes silly videos for the internet (@FentiFriedChicken). He also has a full time job working in Corporate…

Wednesday, May 28th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Las Locas Comedy Presents: Delightfully Unbothered
May28
Music & Comedy

Las Locas Comedy Presents: Delightfully Unbothered

Las Locas Comedy Presents is back at Lincoln Lodge with a brand new comedy showcase – with a brand new name (formerly known as Women…

Wednesday, May 28th
8:00 p.m.9:30 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
Hooch & Holler Comedy Show
May28
Music & Comedy, Theatre & Performing Arts

Hooch & Holler Comedy Show

Every Wednesday The Best Speakeasy In Chicago Hosts The Hottest Comedians The City Has To Offer! Indulge In Our Amazing Craft Cocktails And Enjoy An…

Wednesday, May 28th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Division Street Farmers Market
May29
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.

Thursday, May 29th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Maifest Chicago 2025
May29
Festivals, Fairs & Special Events

Maifest Chicago 2025

Maifest is Back! Admission is free & open to all agesJoin us May 29 – June 1, 2025at our same awesome temporary spot:4521 N. Lincoln…

Thursday, May 29th
5:00 p.m.10:00 p.m.
Maifest Chicago
4521 N. Lincoln Avenue
Teatro Zinzanni
May29
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…

Thursday, May 29th
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Rockin’ in the Park 2025 Free Summer Concert Series
May29
Music & Comedy

Rockin’ in the Park 2025 Free Summer Concert Series

Rosemont’s Parkway Bank Park entertainment district (5501 Park Place, Rosemont) will turn up the volume this summer with the return of its popular “Rockin’ in…

Thursday, May 29th
7:00 p.m.10:00 p.m.
Parkway Bank Park Entertainment District
5501 Park Place
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