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Outdoor festival events in Chicago, IL

Flower Expo Illinois 2025
Tue, Sep 23, 10:00 AM
Heart of Chicago · The Geraghty
Flower Expo Illinois 2025
Tue, Sep 23, 10:00 AM
Heart of Chicago · The Geraghty
Sales end soon
5th Annual COI Connect on the Water in Support of Fellowship Housing
Thursday at 5:00 PM
Near North Side · Wendella Tours & Cruises
Sales end soon
5th Annual COI Connect on the Water in Support of Fellowship Housing
Thursday at 5:00 PM
Near North Side · Wendella Tours & Cruises
Lakefront Sun Set // Solstice’s Summer DJ Lakefront Takeover
Sun, Sep 14, 4:00 PM
Lincoln Park · Theater on the Lake
Lakefront Sun Set // Solstice’s Summer DJ Lakefront Takeover
Sun, Sep 14, 4:00 PM
Lincoln Park · Theater on the Lake
CHICAGO HALLOWEEN BAR CRAWL - 10+ Bars - Nov 1st
Sat, Nov 1, 7:00 PM
Lakeview · Wrigleyville
CHICAGO HALLOWEEN BAR CRAWL - 10+ Bars - Nov 1st
Sat, Nov 1, 7:00 PM
Lakeview · Wrigleyville
Authorless Release Party Tourist Season by Brynne Weaver
Tue, Sep 23, 7:00 PM
Roscoe Village · The Last Chapter Book Shop
Authorless Release Party Tourist Season by Brynne Weaver
Tue, Sep 23, 7:00 PM
Roscoe Village · The Last Chapter Book Shop
Nearly full
Pretty In Pink Skyline Yacht Cruise (Chicago)
Today at 12:45 PM
Grant Park · Anita Dee Yacht Charters
Nearly full
Pretty In Pink Skyline Yacht Cruise (Chicago)
Today at 12:45 PM
Grant Park · Anita Dee Yacht Charters
Sales end soon
Cultures and Conversation
Wednesday at 5:00 PM
West Town · Time Out Market Chicago
Sales end soon
Cultures and Conversation
Wednesday at 5:00 PM
West Town · Time Out Market Chicago
Thrift Denim Festival
Sat, Sep 20, 12:00 PM
Chicago Lawn · Thrift LLC
Thrift Denim Festival
Sat, Sep 20, 12:00 PM
Chicago Lawn · Thrift LLC
Flamenco & Fashion: A Legacy in Motion – World Fashion Festival
Thu, Sep 18, 8:00 PM
The Loop · Macy's
Flamenco & Fashion: A Legacy in Motion – World Fashion Festival
Thu, Sep 18, 8:00 PM
The Loop · Macy's
Chicago Entrepreneurs & Small Business Networking Dinner
Wed, Sep 24, 7:00 PM + 1 more
Lakeview · Barcocina Lakeview
Chicago Entrepreneurs & Small Business Networking Dinner
Wed, Sep 24, 7:00 PM + 1 more
Lakeview · Barcocina Lakeview
“The Recipe” Opening Solo Exhibition by Calvin Coleman!
Fri, Sep 19, 6:00 PM
Bronzeville · Gallery Guichard
“The Recipe” Opening Solo Exhibition by Calvin Coleman!
Fri, Sep 19, 6:00 PM
Bronzeville · Gallery Guichard
La Vie: Afrobeats Day party at Vu Rooftop (SEP 6)
Sat, Sep 6, 3:00 PM
South Loop · VU Rooftop Bar
La Vie: Afrobeats Day party at Vu Rooftop (SEP 6)
Sat, Sep 6, 3:00 PM
South Loop · VU Rooftop Bar
Nearly full
RNB Vs Hip Hop Skyline Yacht Cruise FT: DJ Nehpets (Chicago)
Today at 12:45 PM
Grant Park · Anita Dee Yacht Charters
Nearly full
RNB Vs Hip Hop Skyline Yacht Cruise FT: DJ Nehpets (Chicago)
Today at 12:45 PM
Grant Park · Anita Dee Yacht Charters
The Ultimate Latino Singles Cruise!
Fri, Sep 5, 7:00 PM
South Loop · Chicago Lakefront Cruises
The Ultimate Latino Singles Cruise!
Fri, Sep 5, 7:00 PM
South Loop · Chicago Lakefront Cruises
Tour the Arts Block
Thu, Oct 2, 5:00 PM
Washington Park · Green Line Performing Arts Center
Tour the Arts Block
Thu, Oct 2, 5:00 PM
Washington Park · Green Line Performing Arts Center
First Monday Jazz: Tom Tom's Big Band
Mon, Sep 8, 7:00 PM
Washington Park · The Arts Lawn
First Monday Jazz: Tom Tom's Big Band
Mon, Sep 8, 7:00 PM
Washington Park · The Arts Lawn
Crawloween: River North Halloween Bar Crawl
Fri, Oct 31, 6:00 PM
River North · 222 W Ontario St
Crawloween: River North Halloween Bar Crawl
Fri, Oct 31, 6:00 PM
River North · 222 W Ontario St
Slow It Down Sundays “Sundresses on The Rooftop”
Sun, Sep 21, 4:00 PM
South Loop · VU Rooftop Bar
Slow It Down Sundays “Sundresses on The Rooftop”
Sun, Sep 21, 4:00 PM
South Loop · VU Rooftop Bar
Selling quickly
2025 Chicago Halloween Bar Crawl All Access (13th Annual)
Fri, Oct 31, 8:00 PM
River North · Lincoln Park, River North, Wicker Park Venues
Selling quickly
2025 Chicago Halloween Bar Crawl All Access (13th Annual)
Fri, Oct 31, 8:00 PM
River North · Lincoln Park, River North, Wicker Park Venues
The Design Summit for Friends of Friends
Fri, Sep 26, 1:00 PM
Maplewood · Kimball Arts Center
The Design Summit for Friends of Friends
Fri, Sep 26, 1:00 PM
Maplewood · Kimball Arts Center

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