2021 Chicago Summer Festival Guide

The Taste of Lincoln Avenue returns July 24-25, 2021. (Courtesy of Special Events Management)The Taste of Lincoln Avenue returns July 24-25, 2021. (Courtesy of Special Events Management)

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Neighborhood street festivals, art shows, outdoor concerts — including Lollapalooza and the Taste of Chicago — are returning this summer as the Chicago area reopens.

As with most things this year, the coronavirus pandemic has put its stamp on summer events: some have been postponed until later in the season, some outright canceled for 2021; others are finalizing dates and details. We’ll keep this list updated as more information is available.

Learn more about each event from the organizers themselves by clicking the links below.

September Jump to: October

Roscoe Village Burger Fest fires up the grills Sept. 4-5, 2021. (Courtesy of Special Events Management)Roscoe Village Burger Fest fires up the grills Sept. 4-5, 2021. (Courtesy of Special Events Management)

Sept. 23-26: Manteno Oktoberfest | Map

Sept. 24: Brookfield Art Walk | Map

Sept. 24-25: West Town Art Walk | Map

Sept. 24-26: Andersonville Homecoming | Map

Sept. 24-25: Chicago Gourmet (Loop) | Map

Sept. 24-26: Apple Fest (Long Grove) | Map

Sept. 24-26: Oktoberfest Chicago (Lakeview) | Map

Sept. 25: Elim Dutch Fest (Crestwood) | Map

Sept. 25: Homewood Fall Fest | Map

Sept. 25: Beer in the Woods (North Park) | Map

Through Sept. 25: Fall Bulb Festival | (virtual)

Sept. 25-26: Puerto Rican Festival (Humboldt Park) Map

Sept. 25-26: Hyde Park Jazz Festival | Map

Through Sept. 26: American Craft Exposition | virtual


Fiesta Back of the Yards

Harvest Day (Garfield Park) 

— Hyde Park Summer Fest

Little Italy Fest-West (Addison) 

Oaktoberfest (Oak Park)

— Taste of Polonia (Jefferson Park) 

October Jump to: September 

(The Great Highwood Pumpkin Festival / Facebook) (The Great Highwood Pumpkin Festival / Facebook)

Oct. 1-2: Oktoberfest (Naperville) | Map

Oct. 1-3: Chicago Pride Fest (Lakeview) | Map

Oct. 1-3: Lincoln Square Greek-tober Fest | Map

Oct. 1-3: St. Benedict’s Oktoberfest (North Center) | Map

Oct. 2: Woodstock Ale Fest | Map

Oct. 2: Chicago Food Truck Festival (North Park) | Map

Oct. 2: Glenview Blocktoberfest | Map

Oct. 2-3: WingOut Chicago (Old Town) | Map

Oct. 2-3: Lincoln Square Ravenswood Apple Fest | Map

Oct. 2-3: Spring Awakening Autumn Equinox (Near West Side) | Map

Oct. 3: Autumn Opener (Woodridge) | Map

Oct. 3: Fall Downtown Wine Walk (Naperville) | Map

Oct. 3: The Last Straw Fall Event (Westmont) | Map

Oct. 3: Andersonville Wine Walk | Map

Oct. 8-10: Lincoln Park Wine Fest | Map

Oct. 8-10: The Great Highwood Pumpkin Festival | Map

Oct. 8-31: Fall Fest (Lincoln Park) | Map

Oct. 9: Fall Festival at Cantigny Park (Wheaton) | Map

Oct. 9: Uptown Church Fall Festival | Map

Oct. 9: Northbrook Autumn Fest | Map

Oct. 9-10: Fall Family Festival (Glenview) | Map

Oct. 9-24: Boo at the Zoo (Brookfield) | Map

Oct. 13-17: Night of 1,000 Jack-o-‘Lanterns (Glencoe) | Map

Oct. 16: Family Fall Fest (Elmhurst) | Map

Oct. 16: Fall Family Festival (Hinsdale) | Map

Oct. 17: Fall Fest Express at Lombard Common | Map

Oct. 20-24: Night of 1,000 Jack-o-‘Lanterns (Glencoe) | Map

Oct. 23: Fall Festival at North Park Village Nature Center | Map

Oct. 24: Halloween Happening (Naperville) | Map

Oct. 29: Boo Bash (Northfield) | Map

Oct. 30: Day of the Dead (Pilsen) | Map

Oct. 30: Arts in the Dark (Loop) | Map

Oct. 30: Wheaton Haunted Flea Market | Map

Oct. 30: BatFest (Batavia) | Map

Oct. 31: Northalsted Halloween Parade (Lakeview) | Map


— Autumn Brews (Glencoe)

Nightmare on Chicago Street (Elgin) 

Spooky Pooch Parade (Glencoe) 

Events listed are subject to change. We recommend double-checking times and locations before you head out the door. Do you know of a festival that we missed?  Send us an email.

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