Things To Do in Chicago

Chicago is one of Drew and my favorite cities to visit for a quick weekend. There’s always plenty to see and do and we discover something new with every visit. Below are a few of our favorite things to do in Chicago and places that we recommend to our friends and family whenever they go!

What To See and Do

Cubs or White Sox game – If it’s baseball season, take your pick and visit one of Chicago’s baseball stadiums. We’ve been to both and had a blast, but probably prefer Wrigley Field due to it’s rich history and nearby Wrigleyville for pre- and post-game fun.

Chicago Cubs Wrigley Field

Hamilton – Hamilton does a digital lottery for wicked cheap tickets—you have to enter two days before the show you want to see, but it’s an amazing deal if you get tickets. Enter the lottery here:

Architecture Boat Tour – I know this sounds super lame and touristy, but it’s truly one of the best ways to spend an afternoon seeing the city if the weather is nice. Chicago’s architecture is world-renowned and there’s lots of interesting stories behind the buildings lining the Chicago River. On our most recent visit, we booked our tour through Wendella and had a great time!

Second City – If you’re looking for a laugh, head to Second City for a hilarious improv comedy show. Second City boasts alumni like Tina Fey, Chris Farley, Bill Murray, and Keegan-Michael Key, so you know you’re going to see some talented people at the show. Tickets can be purchased here:

Cloud Gate, Millennium Park, and Grant Park – We end up at the “bean” on every visit to Chicago–gotta do it for the ‘gram! This iconic spot will bring you close to the lake shoreline and along one of Chicago’s most famous streets, Michigan Ave. Don’t miss one of the world’s largest fountains, Buckingham Fountain, located in Grant Park.

Cloud Gate Chicago Millennium Park

Open House ChicagoOpen House Chicago only happens one weekend every year, but it’s a totally fun way to spend an afternoon. Open House Chicago is a free festival that offers behind-the-scenes access to more than 250 buildings across Chicago, allowing you to explore hidden gems and architectural treasures for free. Drew and I happened to visit Chicago on this weekend a few years ago and had a great time checking out interiors of buildings we never would have seen otherwise!

Where To Eat and Drink

Chicago Pizza – I’m a Giordano’s fan. Drew prefers Lou Malnati’s. Either way, you can’t lose. Try both and decide for yourself!

The Signature Room – Technically you will be visiting the Signature Lounge if you’re just going for drinks, but no matter what you’re going to have an amazing view of the city. Skip Willis Tower and just go to the Signature Room. However, prepare for a bit of a wait as the elevators can only hold so many people and have to go up 95+ floors. Also, ladies, be sure to go to the bathroom because the best views are from the windows in the ladies restroom.

The Signature Room Chicago skyline view

Cindy’s – Located at the Chicago Athletic Association hotel, Cindy’s is great for a drink and apps overlooking Millennium Park and the lake. They also are known for brunch, but sadly, we haven’t gotten to try that yet. Another option inside the Chicago Athletic Association hotel is The Game Room–super fun spot to grab a drink and play bocce, foosball, board games, and more!

Sluggers – Located in Wrigleyville, Sluggers is a great spot to grab a bite, have a beer, and swing a bat in the batting cages. Batter up!

Ultimately, any time spent in Chicago is always a lot of fun. If you’ve been to Chicago, what are some of your favorite spots? Anything we must do to next time?

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