🇺🇸 United States

Things to Do in Chicago — September 2026

Explore 355 upcoming things to do in Chicago in September 2026, including I Killed Andy Breitbart and The Best of The Second City. Compare dates, locations…

Find your best match

Choose the event that fits your plan

Search by artist, event or venue, then narrow the list by place, date, event type or price so you can get to the right plan quickly.

355 matches
Filter & sort355 results

Explore Chicago

Switch event type without starting over.

Popular ways to explore

Find the plan that fits

Jump to the date or event type you actually have in mind.

Browse by month

Plan ahead with the Chicago calendar.

355 things to do

Showing 49–72 of 355 · Chicago

No Stress
Concert · Chicago

No Stress

Three Top Lounge

$14.6
Plan your visit

Find the right date and venue

Explore 355 upcoming things to do in Chicago in September 2026, including I Killed Andy Breitbart and The Best of The Second City. Compare dates, locations…

If your schedule is flexible in Chicago, try different dates and nearby venues to uncover more things to do.

Before you book

Check current ticket options

Some events sell in stages or change availability close to the date. Use the current ticket option for the latest purchase details.

Plan the day

Build the rest of the plan

If Apollo Theater and Second City-Chicago: Mainstage are on your shortlist, compare their locations and travel time before choosing a date.

Plan the day

Make more of Chicago

Compare useful dates and event types, then open an event for venue details, ticket information and nearby places.