Do you have a layover or only 1 day to spend in Chicago? If you have 24 hours in Chicago or less, I have put together the perfect one day in Chicago itinerary for 2025 to make the most of your short visit to my hometown. It is a fairly busy itinerary for a day so feel free to skip a few things if you prefer to explore Chicago at a slower pace.
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One Day in Chicago Itinerary (2025)
If you enjoy guided tours, this half day small-group tour, Chicago in a day walking tour and hop-on hop-off bus tour include most of the things covered below.
1) Visit the Skydeck at Willis Tower
The Skydeck at Willis Tower (formerly known as the Sears Tower and what locals still call it) is the most well known of Chicago’s two tall skyscrapers with public observatories. The Willis Tower used to be the tallest building in the world from 1974 until 1998. Lines for the Skydeck can be very long so I recommend visiting in the morning as soon as it opens to avoid the crowds. You can also pay extra for fastpass admission to skip the line or early bird admission (during the weekend only) to enter before it opens to the public. If you are not scared of heights, you can stand on the Ledge which has glass floor balconies that extend over 4 feet from the Skydeck.
(Click here to buy a skip the line ticket)
2) Visit The Bean at Millennium Park
If you have seen any photos of Chicago on instagram or facebook, chances are you are familiar with Cloud Gate (aka “The Bean”), the famous mirrored sculpture located in Millennium Park and one of the most instagrammable spots in Chicago. Millennium Park is free and it is usually crowded (especially in the summer and on weekends) so to avoid the crowds visit early in the morning.
If you are visiting Chicago with children, you might want to also visit Maggie Daley Park, a large public park connected to Millennium Park that has play areas for kids of various ages.
3) Visit the Art Institute of Chicago
Chicago has many great museums which are worth visiting but my top pick is the Art Institute of Chicago conveniently located next to Millennium Park. The Art Institute is one of the oldest and largest art museums in the United States and is frequently found on lists of the top museums in the world. Please note the Art Institute is closed on Tuesdays and Wednesdays. (Click here to buy a fast pass ticket if you want to avoid long lines).
4) Have a meal or drink while enjoying a great view from Cindy’s
If you are hungry or fancy a drink head to Cindy’s, a restaurant and bar on the rooftop of the Chicago Athletic Association Hotel located near Millennium Park. Make sure to spend some time outside on its famous open-air terrace which offers panoramic instagram worthy views of Millennium Park and Lake Michigan. This is a popular spot due to the amazing views and the wait for the elevator can be long but if you visit around the time it opens (10 am on the weekends and 11 am on weekdays) you can enjoy the great views without the crowds.
5) Take an architecture river cruise or walk along the Chicago Riverwalk
Chicago has amazing architecture and the best way to see it is by taking an architecture river cruise. Because the water freezes in the winter, river cruises only operate part of the year (usually between March and November).
If your you are visiting on a warm day, you can also join a combination river and lake cruise.
Another way to enjoy the architecture and river is to take a walk along the Chicago Riverwalk, a pedestrian promenade along the river. The Riverwalk is one of the best spots in Chicago for people and boat watching and it has restaurants, bars and places to sit along the way. You can also hop on a water taxi here during the summer.
6) Hang out at Navy Pier
Some locals consider Navy Pier a bit of a tourist trap, but it is a not to missed attraction if you are visiting Chicago with kids. Navy Pier is full of fun things to do including a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line), Flyover Chicago, the Chicago Children’s Museum in addition to restaurants and shops. Navy Pier is also the starting point for various sightseeing cruises and boat rides.
Tip: If you are visiting Chicago in the summer, you might want to check out the free fireworks at Navy Pier every Wednesday and Saturday night.
7) Enjoy the views from 360 CHICAGO Observation Deck
If you did not visit the Skydeck at Willis Tower or if you want to see great skyline views of Chicago, head to 875 North Michigan Avenue (the building formerly known as the John Hancock Center). There is a public observatory on the 94th Floor named 360 CHICAGO (formerly John Hancock Observatory) which tends to be less busy and has shorter lines that the Willis Tower. The 360 Chicago observation deck has TILT, a enclosed moving platform that tilts you out over Michigan Avenue.
You can buy a skip the line ticket here to save time.
What to Eat in Chicago
Chicago is known for its great food and you can find restaurants serving every type of cuisine here. If you are visiting Chicago for the first time you might want to try deep dish pizza and a Chicago-style hot dog (remember, no ketchup allowed) two foods that Chicago is most famous for. There is a lot of debate which restaurant in Chicago serves the best deep dish pizza but you can’t go wrong with either Lou Malnati’s or Giordano’s, two of the most popular choices with several locations in downtown Chicago. Another restaurant that many locals recommend for its deep dish pizza with a caramelized crust is Pequods which is located in Lincoln Park only a short Uber, Lyft or taxi ride from downtown.
These are my top choices for the best things to do in Chicago if you only have one day.
Check out my 3 day Chicago itinerary if you have more time or want to read about more things to do in Chicago. Also check out my guide to the best time to visit Chicago before planning your trip.
Have you visited Chicago? If so what would you recommend first time visitors see if they only have a day in Chicago?
I LOVE Chicago!! The bean is so fun! There’s also a park in the Lincoln neighborhood called Oz park. There are statues from the Wizard of Oz. So cool!
Never been to Chicago but definitely want to go there for The Bean! I think you have compiled a very helpful list for one-dayers given the fact that most of the crowd visiting Chicago is business. Great job!
My friend and I woke up every day for the sunrise near Millennium Park. So worth it! It was so cool to have the bean all to ourselves. Next time we’re back, taking the boat tour for sure!
I visit Chicago each year and never tire of it! I love the Bean and Millennium Park. Navy Pier is so American for me, especially in summer!
Well, I am yet to plan a trip to Chicago. Not sure when it is going to happen, US is just too far away.
I was in Chicago last November and absolutely hated it because of the weather. Your photos make me wanna go back and Cindy’s was one thing from my list that I didn’t get to check off either. Awesome recommendations!
This is an awesome itinerary to get some good eats and see some the main tourist attractions when in Chicago for just a short time! I’ll definitely head back to Cindy’s next time I’m there.
your post made me want to do Chicago RIGHT NOW! It looks amazing and I am saving it for when I plan my trip there. fingers crossed hopefully I get to go next year!
I was born and raised in Chicago, and for me whenever I went into the City I had to go to Uno’s for deep dish, if their crowded and they always are Duo’s is right down the street. If you want really, really great Italian food then you must go to Rosebud’s. They have numerous locations in the City and one in Naperville. If you plan a trip and it’s winter then make sure it’s around Christmas. The City is just beautiful, cold yes, but absolutely beautiful during the holidays.