Things to Do in Chicago This Weekend -- Sports, Other & More
Discover the best things to do in Chicago this weekend (16 Oct - 18 Oct 2026). Find top Sports and Other events at Wrigley Field and more.
Activities in Chicago This Weekend - Your Weekly Events Hub
In a hurry? Here are this weekend's top picks (16 Oct - 18 Oct 2026), directly from our curated event listings:
- National League Championship Series: Chicago Cubs vs. TBD - Home Game 3 (Date: TBD - If Necessary) at Wrigley Field - Sunday, 18 October 2026. Tickets From $615.
- Chicago Architecture Foundation - River Cruise (Multiple Dates and Times) at Chicago Architecture Center - Sunday, 18 October 2026. See tickets on the event page.
- Rising Stars Burlesque Revue at Stars & Garters Theater - Friday, 16 October 2026. Tickets From $79.
- Bright Star Circus at Stars & Garters Theater - Saturday, 17 October 2026. Tickets From $68.
- Carded at Stars & Garters Theater - Saturday, 17 October 2026. Tickets From $63.
- The Seance (Multiple Dates and Times) at Stars & Garters Theater - Saturday, 17 October 2026. See tickets on the event page.
- Sweetest Day Comedy Jam at Wintrust Arena - Saturday, 17 October 2026. Tickets From $123.
- PFL - Professional Fighters League: Liz Carmouche vs. Jena Bishop at Wintrust Arena - Friday, 16 October 2026. Tickets From $48.
- Oso Oso at Reggie's Rock Club - Saturday, 17 October 2026. Tickets From $75.
- Movements at The Salt Shed Indoors - Chicago - Sunday, 18 October 2026. Tickets From $91.
- Jesse Welles at The Salt Shed Indoors - Chicago - Saturday, 17 October 2026. Tickets From $29.
- Tinashe at The Salt Shed Indoors - Chicago - Friday, 16 October 2026. Tickets From $213.
- Waitress at Nederlander Theatre at Ford Center for the Performing Arts - Sunday, 18 October 2026. Tickets From $70.
- Sophie Truax at Subterranean - Sunday, 18 October 2026. Tickets From $58.
- Riley Brothers at Carol's Pub - Saturday, 17 October 2026. Tickets From $85.
Sports in Chicago This Weekend
Chicago's Sports scene is buzzing this weekend. Catch incredible performances at spots like Wrigley Field or Chicago Architecture Center.
Most major venues release last-minute tickets on the day. Check the venue site directly before assuming a show is sold out.
Other in Chicago This Weekend
From spectacular stage shows to cutting-edge events, Chicago offers fantastic Other. Check out events at Stars & Garters Theater or Wrigley Field.
For last-minute tickets:
The best Other in Chicago often release unsold seats on the day of performance. Standing tickets are often the best-value last-minute option in the city.
Things to Do in Chicago on Saturday vs Sunday
A quick comparison to help you plan your weekend.
| Saturday | Sunday |
|---|---|
| Headline gigs & big events: most major concerts and festivals land on Saturday night. | Markets & culture: brunch spots, markets and galleries are usually a Sunday move. |
| Crowds: busy from midday, peaking 1-4pm in central areas. | Crowds: quieter until early afternoon, building from 11am and easing by 3pm. |
| Nightlife: bustling city centre, longer venue hours. | Pace: relaxed cafes, jazz brunches, afternoon sessions. |
Bottom line: Saturday wins for big-ticket events. Sunday is better for a slower, more local feel - markets, galleries, and long lunches.
How to Book Chicago Events
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FAQ
Which area of Chicago is best for a weekend out?
It depends on your vibe. The areas around Wrigley Field and Chicago Architecture Center are usually great starting points for a weekend out.
Is Saturday or Sunday better for things to do in Chicago?
Saturday is better for big events, headline gigs, and festivals. Sunday is better for markets, brunch, and a quieter gallery visit. If you can only pick one day, Saturday gives you more options - but Sunday is less crowded.