How to spend a perfect 24 hours in Chicago

There’s so much to do in the Windy City

A drone photo of Chicago before the Bears played at Soldier Field. (Photo by Quinn Harris/Getty Images) (Quinn Harris, 2020 Quinn Harris)

If you’re anything like me, you love to travel. And after being inside for more than two years, I am absolutely ready to get back out there and visit some of my favorite cities.

One of the first places I went -- once I started to feel safe traveling again, that is -- was a place I’ve visited many times before: Chicago.

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Part of the reason why I traveled to Chicago was because it’s pretty close to home (I live in Metro Detroit), and I also have loads of friends from college who live there, so I wanted to kill a few birds with one stone on my first post-vaccine trip.

I just did a quick weekend, but it got me thinking about how Chicago is the perfect place to visit if you need to get away for just 24 hours.

There is seriously so much to do (it is Chicago, after all), but with the right recommendations, you can have an absolute perfect day in the city.

This is what I would do if I just had 24 hours in the city:


This sort of depends on when you’re arriving in the city, but for this article’s sake, let’s say you arrived the night before. You wake up around 8:30 in the morning and you instantly need coffee and breakfast.

I would hit up Foxtrot, a fast and casual breakfast spot where you can get a quick breakfast sandwich and a coffee to go. There are a few of them in the city, but I would recommend stopping at the one outside of Lincoln Park. That way, you’re close to lots of things to do, and the water.

Speaking of the water, this is what I would do next in my 24 hours in Chicago: The city’s shoreline is Lake Michigan, so it’s wonderful that wherever you are in the city, you’re super close to blue skies and even bluer water.

Exterior view, looking east, at the Shedd Aquarium in Chicago, Illinois, 2019. (Photo by Interim Archives/Getty Images) (InterimArchives2020)

It doesn’t matter if you want to rent a bike, jog or take a leisurely stroll, there are miles of shoreline that you can travel up and down. Personally, I’d take my breakfast sandwich and find a lovely bench to eat at, and then take a walk up and down Lake Michigan until I got to Shedd Aquarium.

Now, I know that going to an aquarium is something you’d probably do with little kids or teens, and if you have them with you, this should 100% be on your list. If not, the Shedd Aquarium is still so cool to check out. I could honestly spend hours in there, but we still have so much more to do!


At this point, after all the walking on Lake Michigan and inside the aquarium, it’s time for some lunch!

There are so many options for a quick lunch in Chicago, but nothing is more Chicago than having a Portillo’s hot dog. There is a location in the heart of the city, so you pretty much have no excuse -- you have to stop.

If it’s your first time in the city, you might as well walk the Magnificent Mile and do some shopping. And it’s not only the shopping; it’s the restaurants, bars and sight seeing along the Magnificent Mile that make it worth checking out.

The John Hancock Building and Plaza are decorated for the Christmas holiday season. (Photo by Chris McKay/Getty Images) (2014 Chris McKay)

It can kind of be like a choose-your-own-adventure part of the day. You can shop, have drinks, check out the historic Chicago Water Tower or visit the top of the John Hancock building for 360 Chicago.

Pro tip: Buy tickets in advance, because they’re cheaper.

After getting in even more steps at the Magnificent Mile, you may be ready for a rest before going out for the evening. We are ALL here for power naps, so why not head back to your hotel or Airbnb for a quick snooze?

Freshen up for dinner and you’ll be ready to go again soon.


There are so many incredible restaurants in Chicago that it’s hard to chose where you should eat.

Obviously, if you’re in the mood for something specific like Italian or Chinese, then you should 100% find one of those restaurants, but if you want just really good food, check out Girl and The Goat.

I had one of the best meals of my life at Stephanie Izard’s Girl and The Goat. Izard won season four of “Top Chef” and went on to open Girl and The Goat, which has now became a Chicago landmark in the restaurant scene.

There is now a Los Angeles restaurant, as well as two other restaurants called Little Goat Diner and Duck Duck Goat, all from Izard.

The menu at Girl and The Goat is small plates, so that means you order a lot and get to share with whoever you’re eating with. It’s obviously fine dining, but there really is something on the menu for everyone. I would suggest getting the green beans as a side. I don’t know what they put on them, but I’ve never had a better green bean in my life.

View of the restaurant Girl & the Goat (at 809 West Randolph Street) in the West Loop neighborhood. (Photo by Interim Archives/Getty Images)

Just make sure you save room for dessert, because there is a Jeni’s Ice Cream a few doors down from Girl and the Goat -- and it’s a must-try if you’re in the city.

Originally from Columbus, Ohio, you can find Jeni’s ice cream in some markets across the country, but nothing beats going to one of the shops. It is the most decadent and rich ice cream you will ever have.

But the night is still young, which means it’s now time to have some after-dinner drinks -- and some fun!

If you’re young and want to have a wild and crazy night, hit up Wrigleyville. There are so many fun bars, like Sluggers and Happy Camper.

Chicago is also known for its comedy scene, and you’d regret visiting the city for one day and not going to an improv show.

The best of all of the comedy theaters, Improv Olympics, sadly closed, but there are still so many places to go see live comedy.

The other big improv theater in Chicago is Second City. When you’ve got alums like Tina Fey, Steve Carell, Stephen Colbert, Amy Poehler and so many more, you know you’re about to see some hilarious comedy.

Just check their website for shows. Some nights, there are even multiple shows a night.

And that’s your 24 hours in Chicago! Truly, you can’t go wrong with whatever you do, and hopefully, you’ve got more than just 24 hours to explore the Windy City. But if all you have available is a day trip, I hope these suggestions make planning your visit just a little bit easier!

About the Author

Jack is a Digital Content Editor with a degree in creative writing and French from Western Michigan University. He specializes in writing about movies, food and the latest TV shows.

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