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Karen & Zach

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Chicago Skyline

Things To Do

Chicago is a great city with so much to do. We listed a few places we recommend visiting while you're here. Take a long weekend and enjoy!

The Second City

230 West North Avenue, Chicago, IL 60614

This comedy club has weekend improv shows and is a typical checkpoint for comedians and actors who end up at SNL.

The Signature Lounge at the 96th

875 North Michigan Avenue, Chicago, IL 60610

Best views in the city. From the top of the iconic Hancock Tower you can see the lake, river, and full city skyline while enjoying some wildly overpriced cocktails.

Chicago River Boat Architecture Tours

465 North McClurg Court, Chicago, IL 60611

Best way to experience the city. It may sound cheesy, but it's incredibly fun. You can sit in an open-top tour boat listening about the history of the city and the design of some of the most famous buildings.

The Bean

Chicago, IL 60601

Update: Unfortunately the Bean and surrounding area will be under construction from August 15 through spring 2024. In our opinion, you're not missing much. The Bean is a polished stainless steel sculpture in downtown Millennium Park which to the misfortune of the artist's original intent looks like a giant bean. It's actual name is Cloud Gate and with it's curved hull and reflective surface was designed to be a "portal between realms" , but I mean come on, it's obviously a just a big ol' bean.

Navy Pier

600 East Grand Avenue, Chicago, IL 60611

Your second spot to hit if you're looking to check off the touristy side of Chicago. Navy Pier has fantastic views of the city, a ferris wheel, and fine dining options to the likes of Bubba Gump Shrimp and Margaritaville.

Giordano's

130 East Randolph Street, Chicago, IL 60601

Chicago has deep dish. This place has deep dish. It might be worth having at least once.

Portillo's & Barnelli's Chicago

100 West Ontario Street, Chicago, IL 60654

Aside from deep dish, Chicago has some good Italian beef and Chicago hot dogs. This is the place to come for either of things! If you do make it here, make sure to get a Cake Shake. You won't regret it.

Piece Brewery

1927 West North Avenue, Chicago, IL 60622

If you want good pizza (not deep dish) visit this place. Good pizza, good beer, good vibes.

Wrigley Field

1060 West Addison Street, Chicago, IL 60613

For anyone who wants to grab a seat at a historic stadium the Cubs will be in town playing the San Francisco Giants on Monday September 4th at 1:20.

Guaranteed Rate Field

333 West 35th Street, Chicago, IL 60616

For any baseball fans who want to spend less money on tickets watching a game at a newer stadium with nicer views and better food the White Sox are also in town playing the Detroit Tigers September 1-3.

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