Glenwood Avenue Arts Festival Celebrates 25 Years
Aug15
Festivals, Fairs & Special Events

Glenwood Avenue Arts Festival Celebrates 25 Years

The Glenwood Avenue Arts Fest (GAAF), the much-anticipated annual tradition in the Rogers Park neighborhood, showcases the work of over 130 artists and more than…

Saturday, August 15th
11:00 a.m.9:00 p.m.
Rogers Park
Ainslie Winmore Block Party
Aug15
Festivals, Fairs & Special Events

Ainslie Winmore Block Party

YOU’RE INVITED! The Ainslie Winmore Block Party is a completely FREE community event designed to bring our diverse neighborhood together for a day of connection…

Saturday, August 15th
12:00 p.m.6:00 p.m.
4848 N Kenmore Ave.
4848 N Kenmore Ave
Taylor Street Little Italy Festival
Aug15
Festivals, Fairs & Special Events

Taylor Street Little Italy Festival

THIS FESTIVAL IS HELD ON TAYLOR STREET (BETWEEN ASHLAND AVENUE AND THROOP STREET) IN CHICAGO, IL. Taylor Street is one of the most historic neighborhoods…

Saturday, August 15th
12:00 p.m.10:00 p.m.
Taylor Street
Soulful Saturday
Aug15
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Soulful Saturday

Join us Saturday, August 15, for an evening of great food, handcrafted cocktails, and smooth R&B vibes featuring a live performance by Sonic Healing. Doors…

Saturday, August 15th
4:30 p.m.8:00 p.m.
Truth Chicago
56 East Pershing Rd
Summer Screenings: On the Road Again
Aug15
Festivals, Fairs & Special Events

Summer Screenings: On the Road Again

In celebration of the 100th anniversary of the founding of Route 66—America’s most iconic highway—this year’s Summer Screenings program will pay homage to the classic…

Saturday, August 15th
6:30 p.m.9:00 p.m.
Chicago Cultural Center and Chicago History Museum
Beethoven Symphony No. 9
Aug15
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Beethoven Symphony No. 9

Giancarlo Guerrero brings the 2026 season to an epic close with none other than Beethoven’s Symphony No. 9, a musical affirmation of humanity on a…

Saturday, August 15th
7:30 p.m.9:30 p.m.
Millennium Park
201 E Randolph Street
Wicker Park Farmers Market
Aug16
Festivals, Fairs & Special Events

Wicker Park Farmers Market

The Wicker Park Farmers Market will return on May 3 for its 26th outdoor season. The market will be open from 8 a.m. to 2…

Sunday, August 16th
8:00 a.m.2:00 p.m.
Wicker Park
1425 N. Damen Ave
Chicago Air and Water Show
Aug16
Festivals, Fairs & Special Events

Chicago Air and Water Show

The Chicago Air and Water Show presented by the City of Chicago is the largest FREE show of its kind in the United States. The…

Sunday, August 16th
10:30 a.m.3:00 p.m.
North Avenue Beach
1600 N. Lake Shore Dr.
Flight Deck: Air Show Rooftop Watch Party at Offshore
Aug16
Festivals, Fairs & Special Events, Sports & Recreation

Flight Deck: Air Show Rooftop Watch Party at Offshore

The Chicago Air & Water Show meets the world’s largest rooftop at Offshore on Navy Pier, the prime spot to watch as fighter jets thunder…

Sunday, August 16th
11:00 a.m.4:00 p.m.
Offshore Chicago
1000 East Grand Avenue
Glenwood Avenue Arts Festival Celebrates 25 Years
Aug16
Festivals, Fairs & Special Events

Glenwood Avenue Arts Festival Celebrates 25 Years

The Glenwood Avenue Arts Fest (GAAF), the much-anticipated annual tradition in the Rogers Park neighborhood, showcases the work of over 130 artists and more than…

Sunday, August 16th
11:00 a.m.7:00 p.m.
Rogers Park
12th Annual South Shore Summer Fest
Aug16
Festivals, Fairs & Special Events, Music & Comedy

12th Annual South Shore Summer Fest

Join us for the 12th Annual South Shore Summer Festival at the historic South Shore Cultural Center, where thousands of residents, families, businesses, and visitors gather…

Sunday, August 16th
12:00 p.m.8:00 p.m.
South Shore Cultural Center
7059 South South Shore Drive
Taylor Street Little Italy Festival
Aug16
Festivals, Fairs & Special Events

Taylor Street Little Italy Festival

THIS FESTIVAL IS HELD ON TAYLOR STREET (BETWEEN ASHLAND AVENUE AND THROOP STREET) IN CHICAGO, IL. Taylor Street is one of the most historic neighborhoods…

Sunday, August 16th
12:00 p.m.10:00 p.m.
Taylor Street
Sound Bath Live – Lincoln Park
Aug16
Festivals, Fairs & Special Events

Sound Bath Live – Lincoln Park

Looking to relax? This is for you. For 60 minutes, lie back, close your eyes, and let crystal singing bowls, chimes, ocean drum, buffalo drum…

Sunday, August 16th
1:00 p.m.2:00 p.m.
2217 n clybourn ave
2217 N Clybourn Ave
Bespoke Living: Enter the World of Niche Luxury by FGI Chicago and PROVENANCE
Aug16
Festivals, Fairs & Special Events

Bespoke Living: Enter the World of Niche Luxury by FGI Chicago and PROVENANCE

PROVENANCE by Diana Michelle and FGI Chicago welcome guests into the world of bespoke living through an immersive experience of creative bespoke designs, niche fragrances,…

Sunday, August 16th
2:00 p.m.4:00 p.m.
900 North Michigan Shops
900 North Michigan Avenue
Millennium Park Summer Film Series
Aug18
Festivals, Fairs & Special Events

Millennium Park Summer Film Series

Presenting Sponsor Wells Fargo Sinners (2025, R) Guests may take a seat at the Jay Pritzker Pavilion or lounge on the Great Lawn as crowd-pleasing…

Tuesday, August 18th
6:30 p.m.9:00 p.m.
Millennium Park – Jay Pritzker Pavilion
201 E Randolph St
Blackstone Book Club
Aug19
Festivals, Fairs & Special Events

Blackstone Book Club

The Community Reads Book Club bridges the world of the stage with the lives of Chicagoans, transforming the traditional theatregoing experience into a vibrant, neighborhood-driven…

Wednesday, August 19th
Blackstone Branch at the Chicago Public Library
4904 S. Lake Park Avenue
Spotlight Reading Series: A Century of Black Progress
Aug19
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Theatre & Performing Arts, Tours & Attractions

Spotlight Reading Series: A Century of Black Progress

Featuring the most ambitious programming to date, Court Theatre’s 2026 landmark Spotlight Reading Series is organized around the theme “A Century of Black Progress” and…

Wednesday, August 19th
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
NoMI Garden Golden Hour
Aug19
Festivals, Fairs & Special Events

NoMI Garden Golden Hour

NoMI Garden Golden Hour Wednesdays from 5:00 p.m. – 7:00 p.m. Reserve a Table   |   View Menu Introducing our new summer series, NoMI Garden Golden…

Wednesday, August 19th
5:00 p.m.7:00 p.m.
NoMI Garden
800 N. Michigan Ave
HACK JOB, A Comedy Show
Aug19
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

HACK JOB, A Comedy Show

HACK JOB COMEDY A biweekly showcase of Chicago’s best comedians at Blind Barber in Fulton Market! SHOW DETAILS: Doors @ 6 pm Show @ 7…

Wednesday, August 19th
6:00 p.m.8:30 p.m.
Blind Barber
948 W Fulton Market
Summer Screenings: On the Road Again
Aug19
Festivals, Fairs & Special Events

Summer Screenings: On the Road Again

In celebration of the 100th anniversary of the founding of Route 66—America’s most iconic highway—this year’s Summer Screenings program will pay homage to the classic…

Wednesday, August 19th
6:30 p.m.9:00 p.m.
Chicago Cultural Center and Chicago History Museum
The Dramatic Improv Festival
Aug20
Festivals, Fairs & Special Events, Theatre & Performing Arts

The Dramatic Improv Festival

The Dramatic Improv Festival returns to Chicago, August 20-23 for four days celebrating the art of grounded, human, emotionally authentic improvisation. Hosted by Theatre Momentum,…

Thursday, August 20th
The Edge Theater
5451 N Broadway Ave, Chicago, IL, 60640
Daley Plaza Farmers Market
Aug20
Festivals, Fairs & Special Events

Daley Plaza Farmers Market

Chicago Farmers Markets sell fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds – at Chicago’s longest running farmers market on Daley…

Thursday, August 20th
7:00 a.m.2:00 p.m.
Daley Civic Center
50 W. Washington St.
Water Tower Place Hosting “City Market IRL” Weekly Summer Night Market Series
Aug20
Festivals, Fairs & Special Events

Water Tower Place Hosting “City Market IRL” Weekly Summer Night Market Series

Starting July 9, 2026, Water Tower Place will play host to City Market IRL, a new evening market experience that blends local food, artisan vendors,…

Thursday, August 20th
4:00 p.m.8:00 p.m.
WATER TOWER PLACE – Level 4, Michigan Ave.
835 N. Michigan Ave.
Thursday Night Farmers Market
Aug20
Festivals, Fairs & Special Events

Thursday Night Farmers Market

The Wicker Park Bucktown Chamber of Commerce has announced the launch of a new weekly Farmers Market at Walsh Park, beginning June 4 and continuing…

Thursday, August 20th
4:00 p.m.8:00 p.m.
Walsh Park
1722 N Ashland Ave