Being one of the biggest cities in the country, Chicago offers a lot of different ways to relax and be entertained, a lot of which is free. Chicago has plenty of sights and lots of ways to catch a laugh or have a good time, so I’ll do my best to break all of these places into two different posts, one for free things to do and one for some things to do that require that you shell out some cash.

Art Institute of Chicago—One of the best art museums I’ve been to, hands down. We spent a good amount of time here, and there were so many interesting things to see that it was hard to get bored. They have a huge range of famous names: Picasso, Matisse, Rodin, Renoir, Warhol, O’Keeffe, Rivera…the list goes on and on. They also have a number of iconic paintings and works, like American Gothic (Wood), The Old Guitarist (Picasso), and some Chagall windows. On their lower floor, they have an exhibit of Thorne’s Miniature Rooms which was something cool and unique to see. Ferris Bueller goes here on his famous day off, and there are a number of places to see in this museum that he and his friends visit, like A Sunday Afternoon on the island of La Grande Jette. I particularly liked the impressionist collections, and we spent a good amount of time in that gallery. Bring your student ID for reduced admission ($17 with ID, $23 adults).

Second City—If Tina Fey, Amy Poehler, and Steve Carell all come from the same place, you know that place has to be doing something right. Second City’s a comedy club (not too far from a Lou’s!) and school where young actors go to practice and learn improv and comedy. They put on a number of shows, and we went to their Second City E.T.C. stage revue. With a cast of six actors, they put on a hilarious show, which I can never do justice to in writing about it. There were a lot of quotable moments, as well as some that resembled the Kabarett (like when they played on the audience’s lack of knowledge about U.S. history), and we barely stopped laughing the whole time we were there. I absolutely would go back and definitely recommend going to a show if you’re in Chicago. Platform tickets are around $23.
Chicago Architecture Foundation Boat Tour—Chicago has a lot of famous architecture: from the Sears Tower (now Willis Tower) which was the tallest building in the world for 24 years to the new, controversial Trump Tower. Chicago’s skyline is impressive, so it’s only natural to learn more about it. We hopped on a boat tour through the Chicago Architecture Foundation and were guided along the Chicago River by our incredible volunteer docent Rebecca, who told us all about the different prominent architecture styles in the city (art deco, converted warehouses, modern, contemporary), the buildings’ architects, and some Chicago history. Make sure to go on a nice day, because fog swept through the city frequently over the weekend (I think from Lake Michigan) and hid some of the taller buildings in the clouds.
Wrigley Field—The second most loved ballpark in America (after Fenway of course), Wrigley’s another beautiful ballpark filled with energetic fans. The game we went to was a complete washout, so it was delayed for two hours, but once it started it was great (although the Cubs lost to the Pirates). A player from the Pirates hit a homerun right into our section of the bleachers, so everyone yelled “throw it back” by Wrigley customs (also Rookie of the Year). Even though it rained, it was a great and fun ballpark to visit.
I truly believe that Chicago is the best city in the world. I feel so lucky to live here!
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Hi rorypeppercorn, I’m definitely a fan of Chicago now and wish I lived there! Thanks for the comment!
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Sounds awesome, I really need to visit Chicago!
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Hi Alex, it really is awesome! There’s so much to do and the city has an incredible vibe, making it a great city to get away to.
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