Mandatory Photo Credit: Abel Arciniega :: @tequilagraphics

Upcoming Chicago Events

Name: Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival
Start: 2026-01-10T19:00:00-06:00
End: 2026-01-10T21:30:00-06:00
Location: Chicago Dramatists

Check out what's happening all around Chicago.

December 19, 2025: Dec19
Sports & Recreation
PBR – Unleash The Beast
Professional Bull Riders (PBR) is bringing the thunder back to the Windy City for the 16th time as the premier PBR: Unleash The Beast series…
West Loop
Event details
Friday, December 19th
7:45 p.m. – 10:00 p.m.
See all events in series
United Center
1901 W Madison St,
December 20, 2025: Dec20
Theatre & Performing Arts
The Beatrix Potter Holiday Party
Four adorable Beatrix Potter favorites come to life in this mesmerizing, interactive trunk and puppet show, complete with original music. Storytellers weave Potter’s classic narration…
West Loop
Event details
Saturday, December 20th
9:30 a.m. – 10:30 a.m.
See all events in series
Chicago Children’s Theatre
100 S Racine Ave
Dec20
Sports & Recreation
PBR – Unleash The Beast
Professional Bull Riders (PBR) is bringing the thunder back to the Windy City for the 16th time as the premier PBR: Unleash The Beast series…
West Loop
Event details
Saturday, December 20th
6:45 p.m. – 9:00 p.m.
See all events in series
United Center
1901 W Madison St,
December 21, 2025: Dec21
Theatre & Performing Arts
The Beatrix Potter Holiday Party
Four adorable Beatrix Potter favorites come to life in this mesmerizing, interactive trunk and puppet show, complete with original music. Storytellers weave Potter’s classic narration…
West Loop
Event details
Sunday, December 21st
9:30 a.m. – 10:30 a.m.
See all events in series
Chicago Children’s Theatre
100 S Racine Ave
December 23, 2025: Dec23
Sports & Recreation
Chicago Blackhawks vs. Philadelphia Flyers
Come cheer on the Blackhawks!
West Loop
Event details
Tuesday, December 23rd
8:00 p.m. – 9:30 p.m.
United Center
1901 W Madison St,
December 26, 2025: Dec26
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
Friday, December 26th
6:00 p.m. – 11:30 p.m.
See all events in series
City Winery
1200 West Randolph Street
Dec26
Sports & Recreation
Chicago Bulls vs. Philadelphia 76ers
Come cheer on the Bulls!
West Loop
Event details
Friday, December 26th
7:00 p.m. – 8:30 p.m.
United Center
1901 W Madison St,
December 27, 2025: Dec27
Theatre & Performing Arts
The Beatrix Potter Holiday Party
Four adorable Beatrix Potter favorites come to life in this mesmerizing, interactive trunk and puppet show, complete with original music. Storytellers weave Potter’s classic narration…
West Loop
Event details
Saturday, December 27th
9:30 a.m. – 10:30 a.m.
See all events in series
Chicago Children’s Theatre
100 S Racine Ave
Dec27
Sports & Recreation
Chicago Bulls vs. Milwaukee Bucks
Come cheer on the Bulls!
West Loop
Event details
Saturday, December 27th
7:00 p.m. – 8:30 p.m.
United Center
1901 W Madison St,
December 28, 2025: Dec28
Theatre & Performing Arts
The Beatrix Potter Holiday Party
Four adorable Beatrix Potter favorites come to life in this mesmerizing, interactive trunk and puppet show, complete with original music. Storytellers weave Potter’s classic narration…
West Loop
Event details
Sunday, December 28th
9:30 a.m. – 10:30 a.m.
See all events in series
Chicago Children’s Theatre
100 S Racine Ave
Dec28
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
Sunday, December 28th
5:00 p.m. – 10:30 p.m.
See all events in series
City Winery
1200 West Randolph Street
Dec28
Sports & Recreation
Chicago Blackhawks vs. Pittsburgh Penguins
Come cheer on the Blackhawks!
West Loop
Event details
Sunday, December 28th
6:00 p.m. – 7:30 p.m.
United Center
1901 W Madison St,
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
January 2, 2026: 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
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 9, 2026: 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
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