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Upcoming Chicago Events

Check out what's happening all around Chicago.

December 29, 2025: Dec29
Music & Comedy
Raheem DeVaughn – 20 Lessons of Love Tour
Get ready for a night of soulful vibrancy as multi‑platinum R&B artist Raheem DeVaughn heads to Chicago. Known for his silky vocals and heartfelt lyrics,…
West Loop
Event details
Monday, December 29th
6:00 p.m. – 11:30 p.m.
See all events in series
City Winery
1200 West Randolph Street
Dec29
Sports & Recreation
Chicago Bulls vs. Minnesota Timberwolves
Come cheer on the Bulls!
West Loop
Event details
Monday, December 29th
7:00 p.m. – 8:30 p.m.
United Center
1901 W Madison St,
December 30, 2025: Dec30
Sports & Recreation
Chicago Blackhawks vs. New York Islanders
Come cheer on the Blackhawks!
West Loop
Event details
Tuesday, December 30th
7:30 p.m. – 9:00 p.m.
United Center
1901 W Madison St,
December 31, 2025: Dec31
Sports & Recreation
Chicago Bulls vs. New Orleans Pelicans
Come cheer on the Bulls!
West Loop
Event details
Wednesday, December 31st
6:00 p.m. – 7:30 p.m.
United Center
1901 W Madison St,
Dec31
Music & Comedy
Dru Hill: Tell Me it’s New Years Eve!
Get ready, Chicago — the smooth‑and‑soulful harmony of Dru Hill is hitting the Windy City! Known for their R&B anthems like In My Bed and How Deep Is Your Love, Dru Hill…
West Loop
Event details
Wednesday, December 31st
7:00 p.m. – 11:30 p.m.
See all events in series
City Winery
1200 West Randolph Street
January 1, 2026: Jan1
Music & Comedy
Dru Hill: Tell Me it’s New Years Eve!
Get ready, Chicago — the smooth‑and‑soulful harmony of Dru Hill is hitting the Windy City! Known for their R&B anthems like In My Bed and How Deep Is Your Love, Dru Hill…
West Loop
Event details
Thursday January 1, 2026
6:00 p.m. – 11:30 p.m.
See all events in series
City Winery
1200 West Randolph Street
Jan1
Sports & Recreation
Chicago Blackhawks vs. Dallas Stars
Come cheer on the Blackhawks!
West Loop
Event details
Thursday January 1, 2026
7:30 p.m. – 9:00 p.m.
United Center
1901 W Madison St,
January 2, 2026: Jan2
Sports & Recreation
Chicago Bulls vs. Orlando Magic
Come cheer on the Bulls!
West Loop
Event details
Friday January 2, 2026
7:00 p.m. – 8:30 p.m.
United Center
1901 W Madison St,
Jan2
Theatre & Performing Arts
Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival
Pegasus Theatre Chicago presents the 39th Annual Young Playwrights Festival, January 1 – 24, 2026 at Chicago Dramatists, 798 N. Aberdeen. For nearly four decades,…
West Loop
Event details
Friday January 2, 2026
7:00 p.m. – 9:30 p.m.
See all events in series
Chicago Dramatists
1105 W. Chicago Ave. , Chicago, IL, 60642
January 3, 2026: Jan3
Theatre & Performing Arts
Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival
Pegasus Theatre Chicago presents the 39th Annual Young Playwrights Festival, January 1 – 24, 2026 at Chicago Dramatists, 798 N. Aberdeen. For nearly four decades,…
West Loop
Event details
Saturday January 3, 2026
2:30 p.m. – 4:00 p.m.
See all events in series
Chicago Dramatists
1105 W. Chicago Ave. , Chicago, IL, 60642
Jan3
Sports & Recreation
Chicago Bulls vs. Charlotte Hornets
Come cheer on the Bulls!
West Loop
Event details
Saturday January 3, 2026
7:00 p.m. – 8:30 p.m.
United Center
1901 W Madison St,
Jan3
Theatre & Performing Arts
Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival
Pegasus Theatre Chicago presents the 39th Annual Young Playwrights Festival, January 1 – 24, 2026 at Chicago Dramatists, 798 N. Aberdeen. For nearly four decades,…
West Loop
Event details
Saturday January 3, 2026
7:00 p.m. – 9:30 p.m.
See all events in series
Chicago Dramatists
1105 W. Chicago Ave. , Chicago, IL, 60642
January 4, 2026: Jan4
Sports & Recreation
Chicago Blackhawks vs. Vegas Golden Knights
Come cheer on the Blackhawks!
West Loop
Event details
Sunday January 4, 2026
6:00 p.m. – 7:30 p.m.
United Center
1901 W Madison St,
January 7, 2026: Jan7
Sports & Recreation
Chicago Blackhawks vs. St. Louis Blues
Come cheer on the Blackhawks!
West Loop
Event details
Wednesday January 7, 2026
8:30 p.m. – 10:00 p.m.
United Center
1901 W Madison St,
January 8, 2026: Jan8
Sports & Recreation
Chicago Bulls vs. Miami Heat
Come cheer on the Bulls!
West Loop
Event details
Thursday January 8, 2026
7:00 p.m. – 8:30 p.m.
United Center
1901 W Madison St,
January 9, 2026: Jan9
Sports & Recreation
Chicago Blackhawks vs. Washington Capitals
Come cheer on the Blackhawks!
West Loop
Event details
Friday January 9, 2026
7:00 p.m. – 8:30 p.m.
United Center
1901 W Madison St,
Jan9
Theatre & Performing Arts
Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival
Pegasus Theatre Chicago presents the 39th Annual Young Playwrights Festival, January 1 – 24, 2026 at Chicago Dramatists, 798 N. Aberdeen. For nearly four decades,…
West Loop
Event details
Friday January 9, 2026
7:00 p.m. – 9:30 p.m.
See all events in series
Chicago Dramatists
1105 W. Chicago Ave. , Chicago, IL, 60642
January 10, 2026: Jan10
Theatre & Performing Arts
Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival
Pegasus Theatre Chicago presents the 39th Annual Young Playwrights Festival, January 1 – 24, 2026 at Chicago Dramatists, 798 N. Aberdeen. For nearly four decades,…
West Loop
Event details
Saturday January 10, 2026
2:30 p.m. – 4:00 p.m.
See all events in series
Chicago Dramatists
1105 W. Chicago Ave. , Chicago, IL, 60642
Jan10
Sports & Recreation
Chicago Bulls vs. Dallas Mavericks
Come cheer on the Bulls!
West Loop
Event details
Saturday January 10, 2026
7:00 p.m. – 8:30 p.m.
United Center
1901 W Madison St,
Jan10
Theatre & Performing Arts
Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival
Pegasus Theatre Chicago presents the 39th Annual Young Playwrights Festival, January 1 – 24, 2026 at Chicago Dramatists, 798 N. Aberdeen. For nearly four decades,…
West Loop
Event details
Saturday January 10, 2026
7:00 p.m. – 9:30 p.m.
See all events in series
Chicago Dramatists
1105 W. Chicago Ave. , Chicago, IL, 60642
January 12, 2026: Jan12
Sports & Recreation
Chicago Blackhawks vs. Edmonton Oilers
Come cheer on the Blackhawks!
West Loop
Event details
Monday January 12, 2026
7:30 p.m. – 9:00 p.m.
United Center
1901 W Madison St,
January 14, 2026: Jan14
Sports & Recreation
Chicago Bulls vs. Utah Jazz
Come cheer on the Bulls!
West Loop
Event details
Wednesday January 14, 2026
7:00 p.m. – 8:30 p.m.
United Center
1901 W Madison St,
January 16, 2026: Jan16
Theatre & Performing Arts
Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival
Pegasus Theatre Chicago presents the 39th Annual Young Playwrights Festival, January 1 – 24, 2026 at Chicago Dramatists, 798 N. Aberdeen. For nearly four decades,…
West Loop
Event details
Friday January 16, 2026
7:00 p.m. – 9:30 p.m.
See all events in series
Chicago Dramatists
1105 W. Chicago Ave. , Chicago, IL, 60642
January 17, 2026: Jan17
Theatre & Performing Arts
Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival
Pegasus Theatre Chicago presents the 39th Annual Young Playwrights Festival, January 1 – 24, 2026 at Chicago Dramatists, 798 N. Aberdeen. For nearly four decades,…
West Loop
Event details
Saturday January 17, 2026
2:30 p.m. – 4:00 p.m.
See all events in series
Chicago Dramatists
1105 W. Chicago Ave. , Chicago, IL, 60642

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