Your Ultimate Guide to Chicago Weekend Fun

  |     |   Places to Go, Things To Do

One of the best things about living in Chicago is the sheer number of things there are to do. It’s a world-class city, and there are thousands of attractions and some of the best museums in the country. If you haven’t explored your home much lately, it’s time to get out and about with this ultimate guide to Chicago weekend fun.

A visit to the Art Institute of Chicago is one of the top items on any Windy City bucket list. It has the largest collection of Impressionist art outside of the Louvre, as well as impressive collections of American art. Modern art gets its own wing, and while you’re there you can have lunch at Terzo Piano. This acclaimed restaurant by Chef Tony Mantuano, known for his four-star Italian Spiaggia, uses fresh, local ingredients in its seasonal menu.

Follow your exploration of the world’s best art with a view that can’t be matched. 360 Chicago is located a thousand feet up in the John Hancock Building. While you’re there, if you dare, you can look down on the streets below with Tilt. This attraction is a glass room that tilts down at 45-degree angle so you can get a bird’s eye view. If you just want the view, you can skip the admission and have dinner at The Signature Room or drinks at The Signature Lounge. Both are on floors above the actual observatory.

A night at The Second City is always a good idea. The famous improv club has fostered the talents of famed comedians like Bill Murray, Gilda Radner, Tina Fey, Will Ferrell, and so many more. The Old Town standby has the classic improv mainstage, and they’ve also got a stand-up comedy club called, appropriately, UP. You can even grab a bite to eat while you’re there, at 1959 Kitchen & Bar. The restaurant features a lot of local brews as well as craft cocktails.

On Sunday, head to Chinatown for some dim sum brunch, then take the red line back to downtown and take a tour with the Chicago Architecture Foundation. They’ve got indoor tours when the weather’s bad, and when the river thaws you can take their famous boat tour. They’re all led by docents who have received extensive training and will fill you in on tidbits and trivia about Chicago’s past.

These are some of our favorite ways to play tourist in our own city. What are yours? Let us know on Twitter and Facebook!
 

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