Chicago is one of my favorite cities to visit, as well as being my city of childhood. Loaded with fascinating things to see and do, it is impossible to see all the highlights of Chicago in a day.
Unfortunately, that was all we had on our last visit, so we made some hard choices. As we had people with us who had never been to the city before, we needed to make the most of our one day in Chicago, and we did.
Dividing the city geographically, we opted for Chicago’s key downtown locations over the museums, a personal choice, but we could have gone either way. Both are presented below as single-day itinerary options. Therefore, we’ve got you covered if you have more than a day to spend here.
We began our day in the western suburbs and took the Metra train into Union Station.
Save money with a Chicago CityPASS® ticket
If you have more than one day in Chicago, you can save money on entry fees to nearly everything we recommend below with a Chicago CityPASS® ticket. It provides quick and easy access to several Chicago highlights as well as 48% savings over the total cost of these activities had we paid for them each individually.
Specifically, it includes entrance to the Shedd Aquarium, Skydeck Chicago, and the Field Museum of Natural History, plus two more from this list: Art Institute of Chicago, Museum of Science and Industry, 360 Chicago Observation Deck or Adler Planetarium
Note that the pass’ validity period is nine consecutive days starting with and including the first day you visit an attraction. You have one year from the date of purchase to start using your tickets. Reserve your Chicago CityPASS® ticket here
Chicago in a day – top things to do
With only one day to explore downtown Chicago, you will have to choose from the top things to see and do:
- Get an aerial view of the city from either Skydeck at Willis Tower or 360 CHICAGO at the John Hancock Center.
- Enjoy the architecture from a river cruise
- Visit a museum (if you are downtown for the day, the Art Institute is our top pick)
- Walk through Millennium Park
- Indulge in a Chicago Pizza for dinner
Chicago in a day – option 1: downtown
Skydeck on Willis Tower
(Included in the CityPASS® ticket)
Start your day with an aerial view of the city from one of the two massive skyscrapers.
While both are fabulous opportunities, we opted for the Skydeck in Willis Tower (formerly called the Sears Tower). It was once the world’s tallest building, although today it is the third tallest in the USA.
The far-reaching and impressive views from the Skydeck on the 103 floor can include up to four states on a clear day. However, it’s the overhanging glass ledge that really got my heart pumping.
When it was our turn, we took tons of photos. So many in fact, we wrote a separate page highlighting our Skydeck experience.
We not only encourage you to get to the top of one of the two buildings, but we also recommend you start your day with this activity.
You can purchase general admission tickets at the entrance, but on the day we visited, people waited upwards of 45 minutes to get out on the ledge. This was a luxury we didn’t have while trying to see Chicago in a day.
We reserved our time in advance and had a skip-the-line ticket. Reserve your preferred entry time in advance here
Art Institute of Chicago
The Art Institute of Chicago is one of the world’s best art museums and the second-largest art museum in the United States (New York’s Metropolitan Museum of Art is the largest).
Most noted for housing the world’s second-largest collection of impressionist work, the museum actually has over 300,000 works from Byzantine to modern art.
Smartphone or other device owners can download a free audio guide here. There is free wifi at the Art Institute.
If you are not planning to enter with a CityPASS® ticket, reserve your skip-the-line entry here.
Millennium Park Bean
This huge reflective sculpture in Millennium Park is the current number one tourist attraction in Chicago. The best part – it’s free and can’t be missed with a stroll through the park.
Can you spot us in the reflection in the second shot? We are standing underneath the sculpture.
River cruise highlighting the city’s architecture
Chicago is famous for its eclectic mix of architectural styles, including being the birthplace of the American skyscraper. There is no better way to see the variety of architecture than from the Chicago River.
While there are several companies that run tours, we opted for the Architecture Foundation (CAF) river cruise aboard Chicago’s First Lady Cruises and found it to be an excellent choice. We share some of the eclectic architecture here, along with stories and photographs. Reserve your CAF river cruise in advance.
If you ask me, I will insist that the world’s best pizza is a stuffed mushroom and spinach pizza from Giordano’s. Honestly, I was so excited to have my favorite pizza that we gobbled it up before I remembered that I wanted a photo. The empty pie plate just wasn’t so attractive.
Chicago in a day – option 2: Museum Row
If you have two days, or if you prefer museums, my other favorite highlight of Chicago is Museum Row. Located a few miles away from the places we visited on this trip, the first three museums listed here are within walking distance of each other.
- Field Museum of Natural History (Included in the CityPASS® ticket)
The first in museum row, it started as part of the 1893 World’s Columbian Exposition. With the financial support of Mr. Marshall Field, the exhibit became Chicago’s first permanent museum. If you are not getting a CityPASS, reserve your entry ticket here.
- Adler Planetarium (CityPASS® option)
The oldest modern planetarium in the Western Hemisphere also boasts the best views of the Chicago skyline, day and night.
- Shedd Aquarium (Included in CityPASS® ticket)
The Shedd Aquarium is home to 32,000 animals, including beluga whales, stingrays, granddad jellies and penguins.
- Museum of Science and Industry (CityPASS® option)
The largest science museum in the Western Hemisphere, this is our top recommendation of things to do in Chicago with kids. It’s a 6-mile drive from museum row and has plenty of parking.
Chicago in a day – option 3: Hop-on-hop-off bus
Like most major cities these days, Chicago has a hop-on-hop-off bus that is a great way to learn about the history of the town and see the maximum number of sites in the least amount of time. Called the Big Bus Chicago, its 11 stops include:
- Chicago Riverwalk
- Willis Tower (and Skydeck Chicago)
- Millennium Park (and the Art Institute)
- Grant Park (Buckingham Fountain)
- Adler Planetarium
- Museum Campus (Shedd Aquarium and Field Museum)
- Sheraton Grand Hotel (plus Aqua)
- Navy Pier
- Old Water Tower and the Magnificent Mile (plus Holy Name Cathedral)
- 360 Chicago (plus Water Tower Place)
- Hard Rock Cafe (plus River North)
There are several pass options, with daytime buses running from 10am to 5pm daily. The Classic is good for 24 hours, while the Premium and Deluxe options are good for 48 hours, the main difference being that the Deluxe option includes a non-stop, single loop 75-minute panoramic night tour on Friday – Monday nights from May to October.
Reserve your Hop-on-hop-off bus here
Note that the pass is valid for either 1 or 2 calendar days (based on your purchase option) from the time of first use. It is valid for six months from the date of purchase. Your pass does not include entry to any locations with a fee.
Final thoughts on seeing Chicago in a day
Once again, I reiterate that Chicago is a fabulous city, one well worth a decent exploration, but if all you have is one day in Chicago, you will need to make some choices.
- Choose destinations near to each other so you don’t spend too much time in transit.
- If you are visiting Chicago for at least a few days, consider getting a CityPASS® ticket and save 48% on five key attractions (all recommended above – Shedd Aquarium, Skydeck Chicago, Field Museum, plus two more from this list: Art Institute of Chicago, Museum of Science and Industry, 360 Chicago Observation Deck or Adler Planetarium). Reserve your CityPASS® here.
Save on your trip with these resources
We use these aggregator companies to save time and money. They do the work for us by providing a list of options, prices, and reviews for anywhere we are travelling worldwide. Plus, we have personally had positive customer service experiences with all of them:
- Flights: we use Expedia for the best and cheapest flight options.
- Hotels: we use Booking.com as they consistently return the best rates and their reviews are from actual guests. However, for self-contained lodging, use VRBO
- Cars: we use RentalCars to find the best deals and dealer ratings.
- Private guides: we often hire private guides from Tours by Locals
- Travel Insurance: we start at InsureMyTrip as they are the best option to compare plans and find the right coverage for you.
Before you book the rest of your trip: Check out our travel resources page for more companies that we use when you travel.
We believe this list to be the best in each category. You can’t go wrong using them on your trip too.
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Which one day in Chicago itinerary will you choose?
More on Chicago you might like…
- 5 Free Things to Do in Chicago: Don’t Miss These Budget-friendly Activities
- Skydeck Chicago: I Stood on a Glass Ledge 103 Floors Above the Street
- Chicago Architecture: Best Seen from the River
- USA Adventure: Places to Visit on a USA Road Trip
All photos on this page are either shot by our team and watermarked as such or stock images from Depositphotos.
Disclaimer: We are frequently provided with complimentary entrances, tours, or sample items to aid in the writing of Albom Adventures. However, the opinions expressed here are strictly our own.
Oh, we love Chicago. And, now that you mention it, Giordano’s may have something to do with that. And maybe Garrett’s, too. Mmmm…we are definitely overdue for a trip! Thanks for bringing back such fond memories.
Giordano’s is my favorite. I could barely wait until the pizza arrived.
Great choice of Chicago highlights. I live near Chicago and used to work a block from Millennium Park. I used to love walking over there on my lunch break and just hanging out for a while.
The Bean in Millennium Park is interesting on its own as well as from a people watching point of view.
I spent about a week in Chicago some years ago but I never “sat in the Ledge.” In fact I’ve never even heard of it, so I envy you for that. I would have liked to do it, but now I lost the opportunity. I don’t think I’m going back there again. I didn’t quite like Chicago to tell you the truth. Other then the Miracle Mile and the River Cruise, I didn’t find it too attractive.
I find big cities interesting for the culture, activity, and architecture.
It’s a beautiful city indeed. We should come back there, we were there briefly only for transit 🙂
Chicago can be a fun city as there is a lot to do.
I have never been to Chicago. I know it is a great city and am really interested to go. That photo in the Skydeck is insane. So cool!
It is a fun city. The Skydeck Ledge was awesome.
Having just left Chicago in the fall, this made me miss the city! Great suggestions as far as museums go–The Field Museum and the Art Institute of Chicago were my top choices! I also think it’s great you made it to the Skydeck. I was so afraid on the ledge and only took a pic of my feet, but I made it out there!
Well done getting out on the skydeck.
It’s weird that there are so many things that resemble things in NYC, they’re just on a smaller scale in Chicago. Except the bean. Nothing like that in NYC. I wonder if the sun’s rays and heat have the same problem as that weird glass building in London that melts people’s cars! Have a good weekend!
Interesting. When I was in New York I thought the same in reverse, a big Chicago. I haven’t heard of problems with the bean, but I don’t live there and now I am curious.
There is no way I could sit on that glass ledge/box. Just looking at that picture makes me toes curl
LOL – It was really incredible.
I have always wondered if Chicago should go on my to-do-list. Thanks for some insight!
It’s a fantastic city really requiring more than a day. (I was there for a few, but visiting friends and family).
I haven’t been to Chicago in years! It looks even more amazing than I remember. You definitely had a nice day. I think you are braver than me sitting on that glass!
LOL – I just did it, didn’t think about it. As for the day, we were really lucky.
Lyn aka The Travelling Lindfields
Chicago is one of those places we visited but managed to miss almost everything. D and I were staying at St Charles and decided we would drive to a point north of the city with our bikes and then cycle along the lake. It was a beautiful day – but not for long. Just as we approached the city the temperature plummeted and we got hit by driving rain. It was a long, slow, wet, difficult cycle back to the car and then to add insult to injury we got caught in awful traffic heading back to St Charles. I do think of Chicago fondly though – as a city we have to go back to. Thanks for the post. It is going in my save pile.
After that story I am surprised you think of it fondly. Sorry you missed the highlights, but now you have a good reason to go back.
The two things I had to do when I went to Chicago was to see American Gothic at the Art Institute and eat the cheeseburger place that inspired the Saturday Night Live Skit — i think the latter dates me!
American Gothic is one of my favorites, but I wish I remember that SNL skit. (It dates me too).
I would have loved doing the river cruise. Okay, I’m a cruiser.
Have a fabulous day. ☺
Of course you would 🙂
Alex J. Cavanaugh
I’d be up for some really good pizza.
According to that globe, your country doesn’t exist…
While most things from memory don’t stack up when I get then again, this pizza does. Giordano’s is still my favorite. And, pretty funny that New Zealand doesn’t exist.
Trekking with Becky
I’ve only seen Chicago in movies and it’s mainly residential neighbourhoods and the airport, so thanks for my first real look at Chicago! 😀 It’s lovely, and I hope to visit some day. 😀
I never really think movies give you a fair look at a city.
I hear very good reports about Chicago, and her really great reports about its food culture. It is a pretty city, isn’t it.
It’s the town of my birth, so I think I am biased. It is a great city.
No photo of the Metra Train – it was one of the highlights of the day (especially with your new best friend – the train conductor entertaining us most of the ride)
It’s more of a guide for other people than a report of our fun day. However, I will agree that he was a highlight of our day.