Things to do
The 13 best things to do over Labor Day weekend in Chicago
Here’s how to make the most of your three-day weekend.
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Restaurants
This massive Mexican fiesta returns to Grant Park next week after a 2025 cancellation due to safety concerns
Gear up for tacos galore and tons of live entertainment.
Restaurants
This cozy Lincoln Park bistro was just named the 2026 Restaurant of the Year by Food & Wine
And not just because of the delicious food they serve.
Travel
The Great Lakes are a largely untapped market for cruise lines. This small company is making sure Chicago doesn’t keep missing the boat.
Victory Cruise Lines is capitalizing on its advantages over much larger competitors.
Shopping
These are Chicago’s top vintage shops for secondhand shopping, according to Yelp
A trio of local vintage boutiques made the list of the most-saved spots for secondhand shopping in the country.
Theater
This century-old Chicago theater could reopen next year after being closed for a decade—but it needs your help
From fixing the iconic marquee to adding a Walk of Fame, the project aims to reopen the Portage Theater within a year.
Things to do
11 free things you probably didn’t know you can do with a Chicago Public Library card
This free-but-mighty card could be saving you thousands of dollars.
Restaurants
The best steakhouse in Chicago will close in less than a month—here’s your last date to dine
Grab your chance to get a juicy ribeye and cold martini while you can.
Things to do
Chicago’s viral Bald-Off returns this weekend—and it’s a very serious competition
The “Baldest Baddie” and “Baddest Baldie” will be crowned.
Discover Time Out original video