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Upcoming Chicago Events

Check out what's happening all around Chicago.

Wolff’s Flea Market Opening Day
Aug24
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, August 24th
6:00 a.m.2:00 p.m.
Wolff’s Flea Market
6920 N Mannheim Rd
Division Street Farmers Market
Aug24
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, August 24th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
EEEEEATSCON Chicago
Aug24
Festivals, Fairs & Special Events

EEEEEATSCON Chicago

EEEEEATSCON Chicago 2025 Details Tickets: On sale July 1 at 10 a.m. CT at eeeeeatscon.com exclusively for Chase cardholders. When: August 23-24, 2025 Chase Sapphire…

Sunday, August 24th
1357 N Elston Ave., Chicago, IL
1357 N Elston Ave.
Glenwood Sunday Market in Rogers Park
Aug24
Festivals, Fairs & Special Events

Glenwood Sunday Market in Rogers Park

The nonprofit Rogers Park Business Alliance (RPBA) announces 23 local vendors for the 16th anniversary season of the Glenwood Sunday Market, which will operate every…

Sunday, August 24th
9:00 a.m.2:00 p.m.
Glenwood Alfresco
The Lawndale Route 66 Festival
Aug24
Festivals, Fairs & Special Events

The Lawndale Route 66 Festival

The Lawndale Route 66 Festival, taking place on Sunday, August 24, 2025, from 10:00 AM to 7:00 PM, along a historic stretch of Route 66…

Sunday, August 24th
10:00 a.m.7:00 p.m.
Chicago’s Historic Route 66 (Lawndale)
3800 W. Ogden Ave.
Thirsty Ears Festival
Aug24
Festivals, Fairs & Special Events

Thirsty Ears Festival

The Thirsty Ears Festival, now in its tenth year, is Chicago’s only classical music street festival.  For two days we close Wilson Ave. to feature…

Sunday, August 24th
1:00 p.m.9:00 p.m.
ACM School of Music
1758 W. Wilson St.
Chicago International Boat Show
Aug24
Festivals, Fairs & Special Events

Chicago International Boat Show

Chicago International Boat Show August 21–24, 2025 | Navy Pier Marina & Festival Grounds The Chicago International Boat Show launches this summer with an all-new…

Sunday, August 24th
2:00 p.m.5:00 p.m.
Division Street Farmers Market
Aug25
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, August 25th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Broadway Night at the Grant Park Music Festival
Aug25
Festivals, Fairs & Special Events, Music & Comedy, Tours & Attractions

Broadway Night at the Grant Park Music Festival

For over 90 years, the Grant Park Music Festival has offered free classical music in the heart of Chicago. This weekend, Celebrate the enduring legacy…

Monday, August 25th
6:30 p.m.10:45 p.m.
Millennium Park
201 E Randolph Street
Division Street Farmers Market
Aug26
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, August 26th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
The Farmer at The Green
Aug26
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, August 26th
11:00 a.m.3:00 p.m.
The Green at 320
320 S. Canal St.
Division Street Farmers Market
Aug27
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, August 27th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Chicago Fireworks Signature Dinner Cruise on Lake Michigan
Aug27
Festivals, Fairs & Special Events, Tours & Attractions

Chicago Fireworks Signature Dinner Cruise on Lake Michigan

Elevate your evening with a delicious dinner and jaw-dropping panoramic views of the Navy Pier fireworks display illuminating the Chicago city skyline! On our Fireworks…

Wednesday, August 27th
6:00 p.m.10:00 p.m.
Division Street Farmers Market
Aug28
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, August 28th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Thursday Night Out
Aug28
Festivals, Fairs & Special Events

Thursday Night Out

Thursday is the new Friday in Downtown Oak Park! Thursday Night Out opens for its 20th Season, every Thursday from June 5 through August 28,…

Thursday, August 28th
5:00 p.m.9:00 p.m.
1010 Lake Street
1010 Lake Street
Division Street Farmers Market
Aug29
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.

Friday, August 29th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Chicago Vegan Farmers Market
Aug29
Festivals, Fairs & Special Events

Chicago Vegan Farmers Market

A weekly farmers market featuring fresh produce, baked goods, vintage clothing and other items has kicked off in West Town — and its offerings are…

Friday, August 29th
4:00 p.m.8:00 p.m.
Liberation Kitchen
2054 W Grand Ave
Taste of Polonia
Aug29
Festivals, Fairs & Special Events

Taste of Polonia

Join us for an unforgettable four-day festival featuring nonstop live music, captivating dance performances, authentic Polish cuisine and beer, engaging exhibitions, local vendors, a lively…

Friday, August 29th
5:00 p.m.10:30 p.m.
Copernicus Center
5216 W Lawrence Avenue
Wicker Park Bucktown’s “First Fridays” Art Walk
Aug29
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions

Wicker Park Bucktown’s “First Fridays” Art Walk

The “First Fridays Art Walk,” organized by the Wicker Park Bucktown Chamber of Commerce, welcomes art enthusiasts to explore the neighborhoods’ vibrant arts scene. All…

Friday, August 29th
6:00 p.m.8:00 p.m.
Jackson Junge Gallery
1389 N Milwaukee Ave
Division Street Farmers Market
Aug30
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.

Saturday, August 30th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Englewood Village Market
Aug30
Festivals, Fairs & Special Events

Englewood Village Market

Grow Greater Englewood’s 6th Annual Englewood Village Market kicks off on Saturday, June 14th to connect residents with Black-owned businesses and activities rooted in Black…

Saturday, August 30th
9:00 a.m.2:00 p.m.
Englewood Village Plaza
5800 S Halsted
WingOut Chicago 2025
Aug30
Festivals, Fairs & Special Events

WingOut Chicago 2025

Discover WingOut Chicago: The Ultimate Chicken Wing Block Party Join us at Gallagher Way in Wrigleyville for Chicago’s most mouth-watering outdoor event of the summer!…

Saturday, August 30th
11:30 a.m.8:00 p.m.
Gallagher Way
3635 North Clark Street
Taste of Polonia
Aug30
Festivals, Fairs & Special Events

Taste of Polonia

Join us for an unforgettable four-day festival featuring nonstop live music, captivating dance performances, authentic Polish cuisine and beer, engaging exhibitions, local vendors, a lively…

Saturday, August 30th
12:00 p.m.10:30 p.m.
Copernicus Center
5216 W Lawrence Avenue
Chicago Fireworks Signature Dinner Cruise on Lake Michigan
Aug30
Festivals, Fairs & Special Events, Tours & Attractions

Chicago Fireworks Signature Dinner Cruise on Lake Michigan

Elevate your evening with a delicious dinner and jaw-dropping panoramic views of the Navy Pier fireworks display illuminating the Chicago city skyline! On our Fireworks…

Saturday, August 30th
6:00 p.m.10:00 p.m.
bean-night

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