Chicago Beer Fest
WHAT: The Field Museum hosts the Chicago Beer Festival, featuring over 65 breweries, and attendees will have access to some of the exhibits.
WHERE: 1400 S. Lake Shore Dr., Chicago
WHEN: Saturday, Oct. 5, 7 p.m.
Lincoln Park Wine Fest
WHAT: The 7th annual Lincoln Park Wine Fest transforms Jonquil Park into an open-air market with tons of wine and food pavilions.
WHERE: 1001 W. Wrightwood, Chicago
WHEN: Friday, Oct. 4 - Sunday, Oct. 6
Lincoln Square Ravenswood Apple Fest
WHAT: The 37th annual Lincoln Square Ravenswood Apple Fest, presented by the Lincoln Square Ravenswood Chamber of Commerce, featuring unique, apple-inspired food and drinks from local vendors and Midwest farmers.
WHERE: Lincoln Avenue between Lawrence and Sunnyside
WHEN: Saturday, Oct. 5 - Sunday, Oct. 6
Naper Settlement Oktoberfest
WHAT: Enjoy traditional German cuisine and beer and tons of music at Naper Settlement Oktoberfest.
WHERE: 523 S. Webster St., Naperville, IL
WHEN: Friday, Oct. 4 - Saturday, Oct. 5
The Great Highwood Pumpkin Festival
WHAT: The 14th annual Great Highwood Pumpkin Festival will go for two World Records: the longest line of pumpkin pies (2,209, set in 2021) and the most jack-o'-lanterns on display (30,581, held by Keene, NH, from 2013).
WHERE: 17 Highwood Ave., Highwood, IL
WHEN: Friday, Oct. 4 - Sunday, Oct. 6
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Boo! At the Zoo
WHAT: Put on your Halloween costume and gather your ghoulfriends, little ghosts and goblins for Boo! At the Zoo, a fun-filled family event.
WHERE: 3300 Golf Road, Brookfield, IL
WHEN: Every Saturday and Sunday in October, through Oct. 20
Chicago Sukkah Design Festival Opening Celebration
WHAT: The Chicago Sukkah Design Festival pairs community organizations in Chicago’s North Lawndale neighborhood with diverse architectural designers to design and construct sukkahs, small outdoor pavilions built for the Jewish holiday of Sukkot.
WHERE: James Stone Freedom Square, 3615 W. Douglas Blvd., North Lawndale
WHEN: Sunday, Oct. 6, 1 p.m.
On Stage: '1776'
WHAT: "1776" puts a human face on the pages of history as the people behind the national icons are determined to do the right thing for a fledgling nation.
WHERE: Marriott Theatre, 10 Marriott Dr., Lincolnshire, IL
WHEN: On stage through Oct. 13
Steve Martin & 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 Chicago's suburbs.
WHERE: Rosemont Theatre, 5400 N. River Road, Rosemont, IL
WHEN: Saturday, Oct. 5, 8 p.m.
Latina Comedy Festival
WHAT: The 3rd annual Latina Comedy Festival features comediennes from all over the country.
WHERE: Multiple venues
WHEN: Runs Thursday, Oct. 3 - Sunday, Oct. 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."
WHERE: Lyric Opera House, 20 N. Wacker
WHEN: Friday, Oct. 4, 7 p.m.
Anderson .Paak and the Free Nationals
WHAT: Singer, rapper, drummer and record producer Anderson .Paak along with the Free Nationals perform at Huntington Bank Pavilion on Northerly Island.
WHERE: 1300 S. Linn White Dr., Chicago
WHEN: Friday, Oct. 4, 8 p.m.
Michael Kiwanuka & Brittany Howard
WHAT: The American and British singer-songwriters Michael Kiwanuka & Brittany Howard bring their joint concert tour to the Chicago Theatre.
WHERE: 175 N. State St., Chicago
WHEN: Saturday, Oct. 5, 7:30 p.m.
Meghan Trainor
WHAT: Pop singer Meghan Trainor brings "The Timeless Tour" to the Allstate Arena.
WHERE: 6920 Mannheim Road, Rosemont, IL
WHEN: Saturday, Oct. 5, 6:30 p.m.