Every year, in the coldest depths of the winter, Chicago Theatre Week gives us a great reason to venture outside. The annual event runs from February 5 to 15, taking over stages throughout the city—from major regional hubs like the Goodman Theatre and Steppenwolf Theatre to intimate spaces such as Raven Theatre. During Chicago Theatre Week, companies offer tickets priced at $15 or $30 (or sometimes less!). You can browse a complete list of participating shows here.
We’re probably not alone in saying that the weekend is always on our minds here at Time Out Chicago HQ. Like you (probably), we spend the workweek daydreaming about the next restaurant to obsess over and obsessively updating our concert calendars. Whether you’re museum-hopping, plotting a day trip to escape the city, or ready to ghost your original plans for something spontaneous, you’ll find plenty of ways to make the most of your weekend in Chicago.
Last updated February 4, 2026: Looking for the best things to do in Chicago this weekend? Whether you’re the designated group chat planner or seeking some last-minute inspiration, we’ve got you covered. This weekend’s highlights include the annual Chicago Auto Show, the final days of Chicago Restaurant Week and the kickoff of Chicago Theatre Week. On a budget? We’ve rounded up some of the best free events in Chicago, too. Scroll down to discover the best events across the city!
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