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Our top picks this week in Chicago

EsDeeKid

September 26

· 07:30pm

Byline Bank Aragon Ballroom

Alicia Witt

September 26

· 07:30pm

Evanston Space

Sunday In The Park With George

February 28

· 05:30pm

Paramount Theatre - Aurora

Chicago Cubs vs. Los Angeles Dodgers

June 6

· 03:30am

Wrigley Field

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Discover what’s next

Concerts

Souvenirs: A Celebration of John Prine

October 8

· 07:30pm

The Chicago Theatre

Houseplant

October 22

· 08:00pm

Garcias Chicago

Couples Therapy

August 29

· 03:30pm

Zanies Comedy Club - Rosemont

Dave Matthews Band

November 7

· 07:30pm

United Center

Theatre

Ragtime

August 30

· 03:00pm

Beverly Arts Center

The Book Of Mormon

November 1

· 06:30pm

Cadillac Palace

West Side Story

August 30

· 02:00pm

George Van Dusen Theatre At North Shore Center For The Performing Arts

Operation Mincemeat

October 11

· 01:00pm

CIBC Theatre

Sports

Boston Red Sox vs. Chicago Cubs

September 27

· 03:05pm

Fenway Park

Premium Tailgate Party: Detroit Lions vs. Chicago Bears

November 26

· 03:30am

Premium Tailgate Lot - Detroit

Milwaukee Brewers vs. Chicago Cubs

September 9

· 06:40pm

American Family Field

Premium Tailgate Party: Chicago Bears vs. New Orleans Saints

November 22

· 03:30am

Premium Tailgate Lot - Chicago

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Chicago Events Schedule 2026

Experience the vibrant Chicago events scene with a diverse lineup of sports, concerts, and entertainment happening throughout the year. One of the most anticipated events is the Chicago Cubs baseball season at Wrigley Field, where fans can enjoy thrilling games against top teams like the Cincinnati Reds, Milwaukee Brewers, Pittsburgh Pirates, and Atlanta Braves. Key dates include games from late august through mid-september, with main performers and notable moments expected to draw large crowds in iconic venues. Wrigley Field, renowned for its historic charm and lively atmosphere, hosts multiple games each week, providing unforgettable experiences for sports enthusiasts.

Beyond baseball, Chicago's top venues such as the United Center and Auditorium Theatre host concerts featuring renowned performers and bands during various festivals and special events. The city also offers a rich calendar of cultural festivals, comedy shows, and live performances, making it a hub for entertainment year-round. Whether you're passionate about sports, music, or cultural experiences, Chicago's dynamic event calendar ensures there's always something exciting to see and do in the Windy City.