One Day In Chicago | Itinerary Guide

You can see a lot with only one day in Chicago. Here are my best ideas on how to make the most of a short stay in this wonderful city.

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1. Pick A Hotel With A Great Location

As we only had one night and one day in Chicago we chose a hotel with a great location. I swear, location is the most important aspect of choosing a hotel when your time is limited. 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.

Our Pick

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 sights. Our room was beautiful and clean, and the standard of the entire place was impeccable. It was also very affordable.

Other Great Options

Virgin Hotels Chicago: Really cool 4 star hotel within walking distance to many major sights. The hotel offers large and unique rooms, a rooftop bar, a nightclub and no less than 5 on-site restaurants. 

Renaissance Chicago Downtown Hotel: Elegant boutique hotel located right by the Chicago River in the Theater District.

St. Jane Chicago: A 4 star hotel with a classy and timeless decor, perfect location.

The Langham Chicago: This 5 star hotel is perfect for those seeking some extra luxury on their trip to Chicago.

2. Eat Delicious Mexican Food At Frontera Grill 

INSTAGRAM / 445 N Clark St.

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.

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.

Things to do with one day in Chicago: See the bean!

4. Explore Millennium Park & Beyond

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. Perfect non-time consuming thing to do with our one day in Chicago.

Things to do with one day in Chicago: route 66!

6. Pop By The Art Institute of Chicago

Right across the street from Route 66 you’ll find The Art Institute of Chicago, which is supposed to be an amazing art museum. A great place to escape the streets for a few hours while having fun exploring magnificent pieces of art. We didn’t prioritize it on this trip, but we’ll definitely save it for later!

7. 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!

8. 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.

Things to do with one day in Chicago: Walk the magnificent mile

9. 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. 

Things to do with one day in Chicago: Dylan's Candy Bar

10. 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.

11. 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. 

Things to do with one day in Chicago: See the original Playboy Mansion.

12. 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.

Things to do with one day in Chicago: Sprinkles cupcake atm

13. 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 on our one day in Chicago. 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.

Book skip-the-line tickets: Here

Things to do in chicago: 360 view

14. Try The Famous Deep Dish Pizza


We couldn’t spend one day in Chicago without trying their famous deep dish 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?

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

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 one day in Chicago. 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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I hope you got some ideas on things to do when you only have one day in Chicago! It truly is an amazing city and I cannot wait to go back to explore more in the future.


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