One Day In Chicago | 13 Things To Do

Here are my ideas on how to make the most of a short stay in this wonderful city.

This post contain affiliate links, at no extra cost to you. As always, all opinions are my own.

1. Pick A Hotel With A Great Location

Location is the most important aspect when choosing a hotel when you only have 24 hours in a city. You want to experience as much as you can and not spend your precious time on transportation back and forth, right? There are plenty of options to consider in Chicago, and I was so pleased with the prices and how much you can get for your money. Lisa and I stayed at the Hampton Inn Downtown Chicago, which was an amazing choice. The location was absolutely perfect as we were within walking distance to most Chicago sites. Our room was beautiful and clean, and the standard of the entire place was impeccable. It was also very affordable – I wish there was a place like this in NYC hahah.

2. Eat Delicious Mexican Food At Frontera Grill 

As soon as we had checked into our hotel and got rid of our luggage, we walked straight to the restaurant Frontera Grill. This place was suggested to us by a friend of mine who lives in Chicago, and boooy are we glad she did. The atmosphere was very laid back and genuine, the staff was very pleasant, and most importantly: the food was to die for. I cannot recommend this place enough. Address: 445 N Clark St.

Experience the best of Chicago in 24 hours - 13 unique things to do.
@ Jessica Maya

3. Take a Picture By “The Bean”

Just admit it, no trip to Chicago is complete without checking out «the bean». Technically called Cloud Gate, this weird and iconic silver bean in Millennium Park is a haven for photographers and any Chicago visitors and it is definitely worth a visit. We grabbed a coffee on our way and had so much fun discovering the different reflections generated by this steel bean. I suggest you go early in the morning to avoid the biggest crowds.

4. Explore Millennium Park

Millennium Park is a great park within the much larger Grant Park, and has a lot of other things to offer in addition to Cloud Gate. You should check out the really unique Crown Fountain, enjoy interesting art pieces at Boeing Gallery (north and south), in addition to soaking in the Chicago skyline from the Exelon Pavilion. Further south you’ll also find other parts of Grant Park with it’s beautiful Buckingham Fountain and so many other sights.

5. Take A Walk Along Route 66

Driving Route 66 is a dream for many people on their visit to the US, and I’m no exception. It’s just one of those things I really want to try before I die, and when I saw that the famous road started one block from Millennium Park we just had to pop by. It’s nothing fancier than a simple sign in the beginning of the street, but the dork in me still loved every minute of it. Across the street you’ll also find The Art Institute of Chicago, which is supposed to be an amazing museum. We didn’t prioritize it on this trip, but we’ll definitely save it for later.

Experience the best of Chicago in 24 hours - 13 unique things to do.

6. Dine In A Dome By The River

Right next to our hotel we stumbled upon the Chicago Riverwalk. It is a waterfront park for pedestrians filled with restaurants, a ton of places to sit and enjoy the view of the river and skyline, boat and kayak rentals, public art gallery, and many other activities. I hear the Riverwalk comes more to life in the warmer months, and it was a bit quiet in freezing January – although absolutely lovely. For the best experience I suggest you book a table in a dome at City Winery Chicago. It looks SO cool!

7. Walk The Magnificent Mile

An upscale part of Michigan Avenue in Chicago is known as The Magnificent Mile, and it’s hard to miss when you’re in town and like to walk everywhere like we do. The Magnificent Mile reminded me of 5th Avenue in New York City with it’s mix of mid-range and high-end shops, restaurants, department stores, interesting statues and famous buildings like the Chicago Water Tower, The Wrigley Building and Tribune Tower. If this sounds like something for you, you should definitely check it out. Read more about things to do here.

Experience the best of Chicago in 24 hours - 13 unique things to do.
Experience the best of Chicago in 24 hours - 13 unique things to do.
Experience the best of Chicago in 24 hours - 13 unique things to do.

8. Get Your Sugar Fix At Dylan’s Candy Bar 

Dylan’s Candy Bar is one of the many shops along Magnificent Mile, and it was one of my favorites. They have a huge selection of candy and candy-related gifts from all over the world, and the store is decorated in a creative and colorful way. It kinda feels like you’ve stepped into some magical place from the world of Willy Wonka! This place simply makes me happy. Even if you don’t buy anything it’s still a fun place to check out for a few minutes if you pass by.  Address: 663 N Michigan Ave

Experience the best of Chicago in 24 hours - 13 unique things to do.

9. Lunch at 3 Arts Club Café

Located inside the classy furniture store Restoration Hardware, 3 Arts Club Café is the prettiest restaurant I’ve seen in a long time. It’s got a comfortable and elegant vibe to it’s courtyard location with marble tables, cozy couches, huge chandeliers, glass roof and loads of decorative trees. OH and they have an indoor fountain (!) as well. Food and drinks were all very tasty and I recommend this place so so so much if you’re ever in Chicago. They don’t do reservations, but you can walk around the gorgeous furniture store while waiting for a seat. Address: 1300 N Dearborn St.

Experience the best of Chicago in 24 hours - 13 unique things to do.

10. Stop By The Original Playboy Mansion

This beautiful building was bought by the famous Hugh Hefner in 1959 and was the original Playboy Mansion before he bought the bigger more famous one in Los Angeles in the 70’s. As Lisa was mildly (extremely) obsessed with Hugh Hefner in her late teens, she was very happy to be able to see this mansion. This may not the most conventional thing to do in Chicago for most people, but as it’s only two blocks from 3 Arts Club Café I’m throwing it out there. Address: 1340 N. State Pkwy

11. Who Needs Cash? Visit A Cupcake ATM Instead

You might have seen this concept on Instagram or other social media, and it is exactly as cool as it looks: the Sprinkles Cupcake ATM. That’s right. Pick the cupcake of your choice on the screen, pay for it, and the cupcake magically appears through the wall. SO FUN. They’re also super delicious and come in many flavors and colors. Just make sure you grab it before the gate closes, Lisa almost lost an arm because I wasn’t done taking pictures hahahah. Address: 50 E Walton St

Experience the best of Chicago in 24 hours - 13 unique things to do.

12. Get The Best View From Chicago 360

We wanted the best view of Chicago from above and chose 360 Chicago observation deck. It’s located in the famous John Hancock Building, 305 meters above Magnificent Mile, and had a breathtaking 360 degree view of the city. It was a fun experience to see the city from above and I’m so glad we had the time to do it. They even had a bar there so we got to enjoy a beer while hanging out in the skies, that’s a gold star from me. I recommend visiting a little while before sunset, so you get to enjoy the view in both daylight and at night. Get your ticket in advance and skip the ticket purchase line.

Experience the best of Chicago in 24 hours - 13 unique things to do.

13. Try The Famous Deep Dish Pizza

We simply couldn’t leave Chicago before we had tried the famous deep dish Chicago style pizza, now, could we? Our choice of restaurant was Lou Malnati’s Pizzeria and Lisa and I split one big pizza between the both of us. Good thing, because we got SO full. I’m glad we tried it, and it wasn’t awful or anything, but I’m pretty sure it was the first and last time for both of us. It was just.. a lot. Hahah. I still recommend you try it if you’re in the city so you get the complete Chicago experience. And who knows, maybe it’s your new favorite? Address: 1120 N State St

Experience the best of Chicago in 24 hours - 13 unique things to do.

Bonus: Grab Drinks At Hooters

Okay okay, this one might seem like a weird thing to prioritize when we only had one day in Chicago. But here’s the story: We ran into an old classmate of mine and his friend on the plane from Stockholm to Chicago. The next day we ran into them again in our hotel lobby – turns out they were staying in the same hotel as us. WHAT are the odds, right? Throughout the day we kept bumping into them on the streets of Chicago, over and over. Eventually we figured we had to grab some drinks together, so we met them at Hooters at the end of the day. Eating greasy food and drinking colorful «Hooterades» was so fun and such a perfect ending to our Chicago trip. Although, maybe not the best idea when our next activity was a 6 hour bus ride to Detroit…… Whoops.

Experience the best of Chicago in 24 hours - 13 unique things to do.
Ohh and I’m pretty sure we saw Kevin McCallister from Home Alone

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Hi, I’m Tina! The chubby fingers behind this travel blog are attached to my body, so I guess that makes me a travel blogger? I enjoy exploring the corners of the world as often as I can, including my own ‘backyard’ in arctic Norway. And I hope you’ll join me on my adventures.

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