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Upcoming Chicago Events

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Thursday Night Out
Aug21
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 21st
5:00 p.m.9:00 p.m.
1010 Lake Street
1010 Lake Street
Adults Night Out: Block Party at Lincoln Park Zoo
Aug21
Festivals, Fairs & Special Events

Adults Night Out: Block Party at Lincoln Park Zoo

It’s the last hurrah of summer! Adults Night Out: Block Party is a night out at the zoo for the 21+ crowd, complete with carnival…

Thursday, August 21st
6:30 p.m.10:00 p.m.
Division Street Farmers Market
Aug22
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 22nd
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Chicago International Boat Show
Aug22
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…

Friday, August 22nd
2:00 p.m.5:00 p.m.
Chicago Vegan Farmers Market
Aug22
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 22nd
4:00 p.m.8:00 p.m.
Liberation Kitchen
2054 W Grand Ave
Wicker Park Bucktown’s “First Fridays” Art Walk
Aug22
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 22nd
6:00 p.m.8:00 p.m.
Jackson Junge Gallery
1389 N Milwaukee Ave
EEEEEATSCON Chicago
Aug23
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…

Saturday, August 23rd
1357 N Elston Ave., Chicago, IL
1357 N Elston Ave.
Division Street Farmers Market
Aug23
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 23rd
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Englewood Village Market
Aug23
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 23rd
9:00 a.m.2:00 p.m.
Englewood Village Plaza
5800 S Halsted
Summer Wine Down at Gallagher Way
Aug23
Festivals, Fairs & Special Events

Summer Wine Down at Gallagher Way

On Saturday, August 23, Gallagher Way transforms into wine country with a laid-back tasting event featuring plenty of wines to sample, live music, floral bouquet…

Saturday, August 23rd
1:00 p.m.8:00 p.m.
Gallagher Way
3635 North Clark Street
Chicago International Boat Show
Aug23
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…

Saturday, August 23rd
2:00 p.m.5:00 p.m.
Thirsty Ears Festival
Aug23
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…

Saturday, August 23rd
2:00 p.m.11:00 p.m.
ACM School of Music
1758 W. Wilson St.
2025 Chicago Summer Whiskey Tasting Festival
Aug23
Festivals, Fairs & Special Events

2025 Chicago Summer Whiskey Tasting Festival

Special Perks from TastingFestivals.com HERE: https://www.eventbrite.com/e/2025-chicago-summer-whiskey-tasting-festival-august-23-tickets-1005024624707?aff=choosechicag&discount=3rd30 Calling all whiskey lovers and connoisseurs… Take your taste buds on a flavor adventure at The Summer Whiskey Tasting…

Saturday, August 23rd
2:30 p.m.6:00 p.m.
Galeria Chicago
9 West Division Street
DreamLoud Day Fest
Aug23
Festivals, Fairs & Special Events

DreamLoud Day Fest

🎤 DreamLoud Day Fest presented by Nialand is a one-of-a-kind outdoor experience celebrating music, creativity, and connection—curated for urban Black creatives and art lovers who…

Saturday, August 23rd
5:00 p.m.9:00 p.m.
SOUTHSIDE SANCTUARY
4702 S KING DRIVE
Zoo Uncorked: Wines & Vines
Aug23
Festivals, Fairs & Special Events

Zoo Uncorked: Wines & Vines

Sip, savor, and explore at Wines & Vines, Brookfield Zoo Chicago’s exclusive 21+ event featuring the grand opening of our breathtaking Tropical Forests habitat! Enjoy a…

Saturday, August 23rd
6:00 p.m.9:00 p.m.
Brookfield Zoo Chicago
3300 Golf Rd
Chicago Fireworks Signature Dinner Cruise on Lake Michigan
Aug23
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 23rd
6:00 p.m.10:00 p.m.
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.
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