Chicago Oktoberfest
WHAT: The Field Museum hosts the Chicago Beer Festival, which brings together more than 65 breweries, and attendees will have access to some of the exhibits.
OR: 1400 S. Lake Shore Dr., Chicago
WHEN: Saturday October 5, 7 p.m.
Lincoln Park Wine Festival
WHAT: The 7th annual Lincoln Park Wine Fest transforms Jonquil Park into an open-air market with tons of wine and food pavilions.
OR: 1001 W. Wrightwood, Chicago
WHEN: Friday October 4 – Sunday October 6
Lincoln Square Ravenswood Apple Festival
WHAT: The 37th Annual Lincoln Square Ravenswood Apple Festival, presented by the Lincoln Square Ravenswood Chamber of Commerce, features unique apple-inspired food and drinks from local vendors and Midwestern farmers.
OR: Lincoln Avenue between Lawrence and Sunnyside
WHEN: Saturday October 5 – Sunday October 6
Naper Colony Oktoberfest
WHAT: Enjoy traditional German food, beer, and tons of music at Naper Settlement’s Oktoberfest.
OR: 523 S. Webster Street, Naperville, IL
WHEN: Friday October 4 – Saturday October 5
The Great Highwood Pumpkin Festival
WHAT: The 14th annual Great Highwood Pumpkin Festival will aim for two world records: longest pumpkin pie line (2,209, set in 2021) and most jack-o-lanterns on display (30,581, held by Keene , NH, as of 2013). .
OR: 17 Highwood Avenue, Highwood, Illinois
WHEN: Friday October 4 – Sunday October 6
Boo! At the zoo
WHAT: Put on your Halloween costume and gather your ghoul, little ghost and goblin friends for Boo! At the Zoo, a fun family event.
OR: 3300 Golf Road, Brookfield, IL
WHEN: Every Saturday and Sunday in October, until October 20
Chicago Sukkah Design Festival Opening Celebration
WHAT: The Chicago Sukkah Design Festival partners community organizations in Chicago’s North Lawndale neighborhood with various architects to design and build sukkahs, small outdoor pavilions built for the Jewish holiday of Sukkot.
OR: James Stone Liberty Place, 3615 W. Douglas Boulevard, North Lawndale
WHEN: Sunday October 6, 1 p.m.
On stage: ‘1776’
WHAT: “1776” puts a human face on the pages of history as the people behind national icons are determined to do the right thing for a fledgling nation.
OR: Marriott Theater, 10 Marriott Dr., Lincolnshire, Illinois
WHEN: On stage until October 13
Steve Martin and Martin Short: “The Dukes of Funnytown”
WHAT: Often redefining comedy with self-deprecating and subversive humor, Steve Martin and Martin Short bring their “The Dukes of Funnytown” to the Chicago suburbs.
OR: Rosemont Theater, 5400 N. River Road, Rosemont, Illinois
WHEN: Saturday October 5, 8 p.m.
Latin comedy festival
WHAT: The 3rd Annual Latin Comedy Festival features comedians from across the country.
OR: Several locations
WHEN: Takes place from Thursday October 3 to Sunday October 6
Patti LuPone: “A Life in Notes”
WHAT: Actress and singer Patti LuPone makes her Lyric Opera of Chicago debut with her new concert, “A Life in Notes.”
OR: Lyric Opera, 20 N. Wacker
WHEN: Friday October 4, 7 p.m.
Anderson .Paak and the Free Nationals
WHAT: Singer, rapper, drummer and record producer Anderson .Paak and the Free Nationals perform at Huntington Bank Pavilion on the North Island.
OR: 1300 S. Linn White Dr., Chicago
WHEN: Friday October 4, 8 p.m.
Michael Kiwanuka and Brittany Howard
WHAT: American and British singer-songwriters Michael Kiwanuka and Brittany Howard perform their joint concert tour at the Chicago Theater.
OR: 175 N. State St., Chicago
WHEN: Saturday October 5, 7:30 p.m.
Meghan Trainor
WHAT: Pop singer Meghan Trainor performs “The Timeless Tour” at Allstate Arena.
OR: 6920 Mannheim Road, Rosemont, Illinois
WHEN: Saturday October 5, 6:30 p.m.
