Chicago for Free: a Vacation to the Midwest

Yes yes yes, I know that this site is called NASHVILLE for free, but no matter how much you love a place sometimes you just have to get the hell outta Dodge. For all the great things that are in Nashville I’ve been feeling a little antsy. I needed a vacation.

As a poor college student I can’t really spend a lot of money to go on a big fancy vacation to someplace like Las Vegas or wherever it is people with money to go party. Hotels, unless they’re incredibly sketchy are absolutely out of the question, as are fancy dinners and taxi cabs.

So, I decided to go visit a good friend in the great city of Chicago. He has a studio apartment near Loyola that has a nice big floor that will fit a nice air mattress, so that took care of the housing situation. Flights to and from Chicago on Southwest are only about $80 each way, and public transportation in the Windy City is easy to use and incredibly affordable.

Of course, none of that would mean much if all interesting activities in Chicago cost big money, but Chi-town has no shortage of awesome free shows, parks, zoos, and exhibits.

Let’s start with a discussion about free music. Nashville has a TON of free music, and a lot of it is pretty good. Live on the Green and Musicians Corner are great examples of Nashville’s great free live music scene. In Chicago, though, I was in heaven. The first night I was there I saw that a singer I’m a fan of, Robbie Fulks, was playing a free show! You might know Robbie from his song “Fuck this Town,” which is about Nashville. I think you’d be right in assuming he’s not a fan of this city. I didn’t actually make it out to see him, but I thought it was really cool that he was playing a free show.

The big free show I saw was part of Texas on Tour at the Navy Pier, which I typically wouldn’t care about since I typically don’t care about Texas. Oh, it’s a great state, but as a non-Texan I pretty much never have Texas on the brain (I apologize to my 20 friends from Texas). Texas, however, can boast some great music, including the Old 97s, who were playing a free show at Navy Pier!

I’ve liked Rhett Miller and the Old 97s since about the 8th grade, but I’ve never gotten a chance to see them, so I was NOT about to miss seeing them play for free. So, my friend and I got to Navy Pier way too early, so we wandered around the huge tourist attraction for awhile. I really enjoyed a free stained glass exhibit they had there, but more than that I enjoyed the Dippin’ Dots I bought from a vendor. It was really freaking hot.

I really enjoyed the Old 97s, like I knew I would. I really enjoy going to shows in places that aren’t traditional music venues. At Navy Pier my friend and I watched the boats float around Lake Michigan while Rhett and the gang played some wonderfully sappy love songs in the background. It was nice.

One of my favorite areas in Chicago is Lincoln Park, partially for the zoo and conservatory there. The Lincoln Park Zoo is famous and free, so I couldn’t resist it. I throughly enjoyed watching the otters and penguins, but although it was cool to be so close to tigers and leopards in the cat house, it made me sad to see them in such confined spaces. Those animals are meant to run long distances in the wild, not sit in a cage and stare at people who are staring at them. Still, it’s a really great zoo, and the price is right.

For the several days I was in Chicago, I don’t think I spent a dime on outside entertainment in the city. I didn’t pay to go to the top of the Hitchcock building, instead I just went to the bar on the 96th floor, I didn’t pay to go to any museums, instead I just looked for free art exhibits here and there like the stained glass exhibit at Navy Pier, and I didn’t pay to see any live music (well, I did go to the last day of Pitchfork Festival, but that wasn’t a part of the vacation so much). Chicago, you did me well!

How about you guys? What free things do you do at your vacation hot spots? How do you save money on vacation?



About Emily

Emily (Founder/Editor in Chief) : Emily is a graduate from Belmont University, where she majored in Music Business. She’s originally from rural Ohio, where there are many cows, a river, and one vineyard. Though she moved to Seattle in 2015, Emily maintains a love of both Nashville and free things, and is actively looking for contributors for If you're interested, reach out to her at

  • Chris

    I too was visiting friends in Chicago this past weekend. We found free swing dancing (including lessons and a live band) at Grant Park, just south of the Navy Pier. And you’re so right about the convenient and inexpensive public transit. I also took advantage of the free, amazing Lake Shore bike trail! Great trip, but it’s good to be back in Nashville.

  • Emily

    My friend talked about the Lake Shore bike trail. We probably would’ve taken it if I had a bike up there, but alas, I do not, so we just went to Hollywood Beach instead.

    It’s a cool town. I like it a lot.