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Overnight Outings: Chicago

1/15/2019

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By: Katelyn Sexton

Chicago. The windy city. Chi-town. The second city. The third most populous city in the United States is just a short 230 miles away from Iowa City, which makes it a necessary venture for those of us living here during our medical tenure. Iowa City is sometimes referred to as Chicago’s favorite suburb because of the very large student population from Chicagoland.

You’d be hard pressed to fit everything you wanted to do in Chicago into an overnight stay. A full weekend getaway is highly recommended! Obviously, Chicago is home to many famous tourist attractions. An entire weekend could be spent doing things you certainly don’t need to read about on a blog. Between Navy Pier, Shedd Aquarium, various art museums, the sky deck on Willis Tower, and shopping on Michigan Avenue, you’d keep plenty a full itinerary without needing any guidance from me! I will say that if you are interested in hitting all the tourist hot spots, look into purchasing a City Pass (www.citypass.com) that will grant you access to everywhere you want to go for one cost all while skipping the lines.

All that said, here I am writing a blog post about visiting the town. One of my brothers lives in Chicago. I’ve been fortunate enough to visit him on several occasions and gotten a glimpse of why people really love the Windy City. Trust me, no one moves to Chicago for the winters! There really is some magic to the city beyond all the tourist traps. And you’ll easily spot plenty of UI tiger hawks all over the city to make you feel at home! Anyway, here’s a short list of things to do that may otherwise fall beneath your radar:

Pizza: Obviously, everyone wants deep dish when they visit. Skip the recommendations you’ve been given and go to Pequod’s in Lincoln Park. You won’t be sorry!

Hotel: I’m an advocate for staying in a short term rental. Try to find an AirBnB or something on HomeAway. It’s the best way to feel acclimated in a new city and you get a kitchen to save some money by buying food! If you’d prefer a hotel, I’ve found reasonable rates at the Hotel Cass, which is in the Loop just a few blocks shy of the Magnificent Mile.

Parks: The city is home to many amazing parks that are 100% free. There’s something really nice about being in a peaceful oasis in the middle of a bustling city. Lincoln Park is one of the more famous parks and even hosts a zoo completely free of charge. There are also amazing hiking trails, such as the 606 hiking trail, in parks around the city to give you glimpses into many different neighborhoods.

Museums: For something off the beaten path, check out the Saturday Night Live exhibit at the Museum of Broadcast Communications.

Food: Other than pizza, Chicago is home to a million incredible restaurants and bars. Some of my personal favorites include Monk’s Pub, Quartino and Taco Joint.

Bike tour: When it’s warm out, I highly recommend Wheel Fun Rentals. It’s a four-person bike to explore the city. It’s a little dorky, but a really fun family activity. Bonus: it’s by the beaches, which are also a must in the summer months.


Chicago is the perfect weekend getaway. I visited several times with my family as a child, and it’s definitely a place with plenty of family-friendly activities, but I’d say that, if possible, a parent-only retreat would be idyllic. Thanks for reading! I hope you enjoy a trip to Chicago during your time in Iowa. 
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