25 Hours in Chicago

As some of you know, I recently went to Chicago over fall break, however, since fall break is relatively short I only got a few hours in the city. Don’t get me wrong though, I loved my time there and wouldn’t change it for anything! Besides, a short vacation is better than no vacation. I’m really excited to try this style of writing to tell you all about my recent trip, as I’ve seen it before on New York Times travel articles.

So, without further ado, I present to you my 25 hours in Chicago.

Millennium Park

October 15:

2:30-9:30 p.m. – On the Road.

Tekamah, Ne to Chicago, Il is a seven hour drive. Yes, I drove there. Crazy, right? It actually wasn’t that bad, it went by really fast and my friend and I took turns driving so we only had to drive about 4 hours each.

9:30-10 p.m. – Airbnb

My friend and I arrived at our quaint little Airbnb and we were so in awe we that spent a lot of time taking pictures and exploring our little attic space.

Millennium Park

October 16:

9:30-10:30 a.m. – The L

Luckily, the Airbnb we were staying at was only a 10 minute walk to Chicago’s Train system and once we navigated our way to that, it was easy to pick out which line we wanted and how to purchase our tickets (well, with help from some locals).

10:30 a.m.-12 p.m. – Millennium Park and Roosevelt University

Millennium Park is home to the famous “Bean” and is located in downtown Chicago as part of the “Loop”. After walking around the park and seeing other modern art sculptures, we were given a tour of Roosevelt University.  It was interesting to see how colleges in other states use their resources, for example Roosevelt University is completely vertical as opposed to a horizontal layout like I see in Nebraska.

12-2 p.m. – Chicago Riverwalk

Like most of the attractions I saw, the Chicago Riverwalk is something free to do. Anyone can walk along the waterway while looking up at beautiful skyline. Buildings I saw here included Trump Tower, the Tribune Tower, Marina City, Wrigley Building and so many more.


3-5 p.m. – Navy Pier

The Navy Pier gives you a breathtaking view of Lake Michigan; it’s a great place for photo ops as you can get the city skyline and the water in the picture! I rode on the Centennial Wheel ($15) which takes riders up 200 feet for even more astonishing views!

5-6:30 p.m. – Dinner 

After walking back to the main Loop of Chicago, my friend and I stopped at Exchequer Restaurant for some local deep dish pizza. The cozy place looked small on the outside but opened up to a large bar area and three separate dining rooms. The dim-lii restaurant was covered in historic newspaper clippings and photos. I order their cheese deep dish pizza and it was brought out almost as quickly as I ate it.

6:30-7:30 p.m. – Airbnb

Once we took the L back to our Airbnb’s neighborhood, we decided to call an Uber as it was darker out this time. We probably walked about 15 miles in total this day so we were ready for bed!


October 17:

8:30-9 a.m. – “Shameless”

After waking up from our long rest, my friend and I got dressed and packed up our belongings and headed outside, stopping to pet the owner’s pet first. We then googled the “Shameless” house from the hit Showtime T.V. program and saw it was only a 15 minute drive from us. We pulled up to the house and took pictures. We were then kindly asked to leave whenever we were finished as they were going to start shooting within the hour! Unfortunately, we had to be back in Nebraska at a certain time so we couldn’t stay to see the actors.

9 a.m.-4 p.m. – Home Again

Seven hours later and I was back in Nebraska!

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  1. Love this roundup for 24 hours in Chicago! I was recently there for work and so only had a bit of time each day to be a tourist – but I was able to fit so much in despite limited time. I think Chicago is a fantastic city for a quick visit.

  2. I grew up visiting Chicago several times a year and love it more now as an adult. It sounds like you had a great time! Thanks for sharing (:

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