I’m not usually one for traveling for less than 2 days, but I spent ~36 hours in Chicago this past weekend in order to meet my mother halfway across the country (she flew in from New Hampshire, I took a red eye from Los Angeles). We had a pretty important reason to do so (final fitting for my wedding dress that she’s making!), but not one that took up a lot of time. This left us with a solid day (afternoon and evening of Saturday plus Sunday until our ~4pm flights) to fill up! I’ve been to Chicago before but only ever in a transient manner: flying into and out of O’Hare or as a road trip pit stop. I hadn’t ever really explored the city and I was psyched to be able to see so much in such a short period of time. If you ever find yourself in The Windy City for a day (or even for a really long layover, the El is surprisingly easy to grab from the airport into downtown), here are my suggestions of what to do:
For a first-stop in the city, I definitely recommend the River Walk! It’s a great way to get acquainted with the Loop as well as the different neighborhoods that border it. Plus you get lots of interesting views around every turn. It’s definitely popular with runners (one of my favorite ways to explore a city!) and tourists alike. If I find myself back in Chicago during the summer, I’m sure this would be a lovely spot to bring a book and an iced tea to relax for a few minutes.
This came up when I searched “free must-dos in Chicago” and I’m so glad I checked it out. The Cultural Center is right next to Millennium Park and a quick walk-through to see everything will only take you about ~20 minutes. It is home to the largest Tiffany Studios glass dome in the world, as well as countless other tile murals, designs, and art installations. Truly a breathtaking building!
Definitely a quintessential Chicago stop, I personally loved the Art Institute and had a blast walking through the many collections. If you only have a short time in the city, I would recommend time-boxing this activity at 3 or 4 hours. That will give you enough time to see the big hits and peruse a few of the galleries, but also leaves the rest of your day open for more exploring!
Another iconic, not-to-be-missed Chi-town spot, Millennium Park, I learned, is best at day break! I happened to take a red eye and immediately upon arriving head to The Bean, which was basically deserted, a sight not often found. I went back later in the day when my mother had arrived and it was teaming with crowds. Definitely recommend an early stop if you can handle it.
Maggie Daley Park (Grant Park)
Maggie Daley Park abuts Lake Michigan, so if you’re there in the winter like I was, this might end up being a quick “see it and leave immediately” excursion. Regardless, I loved gazing out at the water (while jumping up and down to stay warm) surrounded by activities and other passers-by. Grant Park encompasses Maggie Daley as well as Millennium Park, the Art Institute, Buckingham Fountain, and a variety of other attractions. It’s a great one to have as a destination and then to just wander in for an hour or two.
When I left the Merchandise Mart I texted my friend who used to live in Chicago and had recommended it and said, “Love it, I felt like Corduroy!” There’s something about the endless escalators, beautiful high ceilings, and slippery floors that put me back in time. Definitely a fun one, especially if you’re looking for an indoor activity.
Cafes: Peach And Green, Toni Patisserie & Cafe, Goddess And The Baker
With all this walking you’re for sure going to need some sustenance and, if you’re like me, vats of coffee. I stopped by three different cafes on my recent visit, all of which I would definitely recommend. Peach and Green is great for a coffee and quick snack; I loved the pepper and egg sandwich at Goddess and The Baker, and appreciated their free wifi that meant I could camp out for a few minutes with my laptop; and Toni was a fun French find where the Oeuf and Jambon crepe was top notch (also, check in on Yelp for a free macaron)!
Take an El Ride Through the Loop
If you’ve never been to Chicago and are used to standard city metros, the El is an experience I can’t recommend more. The “elevated” transit lines make train rides anything but boring. The Loop, the central downtown area of Chicago, is very accessible by the El and gives you amazing views throughout. I definitely recommend jumping on and off the train anytime you see something that strikes your fancy!
Eat a Portillo’s Hot DogEat a Portillo’s Hot Dog
A quick walk away from the rest of these activities, the adventure to find Portillo’s will give you a better sense of more of the city as you delve into the River North neighborhood. Get the Chicago style dog, the hype is worth it.
Grab a Drink at Game Room, the Chicago Athletic Club Bar
Want to grab a drink but also feeling like you need an activity? Game Room has you covered with delicious cocktails alongside lots of games! The bar is located inside of The Chicago Athletic Club Hotel, which is also beautiful to look around in on your way in.
Anyone else been to Chicago? As big a fan as I am?? Leave your must-dos in the comments!
Great idea sticking to the loop for your first visit! It’s a compact enough neighborhood to really get a sense of it if you’re running low on time.