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
Photo Credit: Chicago’s First Lady Cruises
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.
Another super popular and very highly rate choice is Shoreline Sightseeing Tours. Reserve your Shoreline river cruise here.
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.
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 for later
If you enjoyed this article, please share it on social media and save it for later on Pinterest.
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.