Big and bustling, Chicago can be quite overwhelming. We had one day to spend in Chicago and decided to not merely check off the boxes, but enjoy the city and do the things that we were most interested in.
Last updated: February 2, 2026
Chicago in One Day (or City Layover… If You Wish)
Have you ever wondered if you can sneak out of the airport and explore Chicago during a long layover? After having such a memorable experience during our 6-hour layover in Riga, Latvia, a few years ago, I was tempted to repeat this little feat in Chicago more than once.
What at that time seemed like a possibility proved to be almost impossible during our latest day trip to Chicago. The drive from Chicago O’Hare International Airport to the city center turned into more than an hour, bumper-to-bumper peregrination. Looking at the opposite side of the highway, you could expect the same daunting trip back to the airport.
So, unless you have at least a 12-hour stopover in the city, I wouldn’t recommend leaving the airport.
But we had one day and night to explore the best things and places of Chicago before heading north and continuing our Midwest road trip across Illinois, Wisconsin, and Minnesota.
Spending One Day in Chicago: Things to Know
Chicago has two sides: a bustling city with stunning architecture and walkable downtown and neighborhoods with higher crime rates. The first was our field of exploration. The latter is best to be avoided.
If you have only one day to see the best attractions and places of Chicago, the shady areas fall off of your itinerary automatically. As many of the iconic sites clustered in the city center or near the downtown area, you may even comfortably ditch the car and walk, use public transportation, or Uber while enjoying the day and some night (if it’s your cup of tea) activities of Chicago.
Let’s summarize it quickly before filling your itinerary with places and things you don’t want to miss in Chicago during your one-day visit.
- One day in Chicago is enough to see some of its popular landmarks, experience its diverse food scene, and take a sneak peek at some of the lesser-visited places.
- Be aware of your surroundings, though. Like many large cities, Chicago has safe sides and areas you should leave unexplored. Wandering in the questionable sections of the city during the day or at night shouldn’t be a thing to tick off your Chicago itinerary.
- Downtown Chicago is a walkable, but expansive area. You can explore it on foot or use public transport or a shared ride to get around. Driving is not the best idea. First, during peak hours, you can get stuck at an intersection for a while. Second, free parking is nonexistent in Chicago, at least based on our experience. Since we were mostly interested in places one should never miss while spending a day in Chicago (assuming it’s your first visit), we parked in a paid public structure and explored the city in a traditional way: walking and eating our way through the Windy City.
READ MORE: Two Sides of Bratislava: Royal Old City and Soviet New Town
BEST THINGS TO DO IN CHICAGO IN ONE DAY (FOR FIRST-TIME VISITORS)
1. Stroll along the Chicago Riverwalk
A scenic waterfront path, the Riverwalk presents Chicago in its best colors and from the most pleasing angles. The 1.25-mile path runs along the south banks of the Chicago River. Imposing skyscrapers rise on both sides of the river.
With that said, the Riverwalk is one of the best places to visit in Chicago when you have only one day to immerse yourself in the city culture. Furthermore, it’s the area you can’t miss if you are looking forward to photographing the iconic Chicago’s skyline.
The waterfront path runs primarily along Wacker Drive and is lined up with riverfront public installations, bars, and restaurants.
2. Take an Architecture Tour Cruise
You can see similar impeccable views of Chicago’s skyscrapers accompanied with the stories about the city and its iconic sites from the Chicago River. Ranging from 45 minutes to more than an hour, the guided boat tours offer unique perspectives on familiar landmarks.
3. Take “The Bean” Mirror Selfie in Millennium Park
Located in the heart of downtown Chicago, Millennium Park entices locals and visitors with a wide range of attractions and entertainments. The sites you want to include in your Chicago itinerary are display-changing Crown Fountain, the vibrant Lurie Garden, and the colossal Jay Pritzker Pavilion where free events take place often. We were lucky to attend one of them during our short, one-day trip to Chicago without any prior reservation or planning, for that matter.
The main feature of Millennium Park is, however, The Bean, officially known as Cloud Gate. The Bean is an eccentric public sculpture that resembles, you guessed it… a bean. Its mirror-like steel surface reflects the city’s towering structures. Visitors use it as a “mirror” to take selfies with the city’s skyscrapers in the background.
4. Visit Grant Park
Grant Park is the central urban park in Chicago. In fact, you can spend the entire day in this massive open area gazing at and visiting Chicago’s signature landmarks such as the multi-tiered Clarence F. Buckingham Memorial Fountain, families favorite Maggie Daley Park, the Art Institute of Chicago, and the always inspiring Museum Campus.
Even your visit to Millennium Park is nothing else but a trip to a smaller, modern section of Grant Park. Known as “Chicago’s Front Yard”, the Grant Park encompasses Millennium Park and the areas along Lake Michigan.
5. Visit the Chicago Theater
Once in Chicago, you can’t skip a show at the Chicago Theater. Whether it’s your first or returning trip to the city, whether you plan an extended city adventure or have only one day to see the best of the best, make sure to step inside Chicago’s iconic theater.
If you don’t have time for a live play, take an architecture tour to see the grand lobby, breathtaking auditorium, and sneak to the backstage area. With its walls festooned with celebratory autographs, the latter is a grand arena in its own way.
6. Admire City Views from Skydeck Chicago
A visit to Skydeck Chicago was the main agenda of our one-day trip to Chicago. I admit, it may be the most predictable thing to do in the city. But when the desire is great, there is no need to suppress it, even if you may go off your preferred way of travel and join the crowds for a while.
Skydeck Chicago is a famous top floor of the 1,451-foot (1,729 to tip) Willis Tower. Equipped with a few glass ledges, it offers the bird’s eye views of Chicago and Michigan Lake. On a clear day, the vistas from the 103s floor of the Willis Tower surpass Chicago city limits, spanning up to 50 miles and four states.
READ MORE: The 4 Best Views of Vancouver, B.C.: Vancouver from Above
7. Ride Centennial Wheel at Navy Pier
If you spend a day in Chicago with a kid or want to reunite with the little kid inside you, there is no better way to combine some beautiful sightseeing with the thrill of adventure than jumping on the Centennial Wheel. Located at Navy Pier, a venue for many free events, the Farris wheel offers the stunning views of Chicago’s skyline and Lake Michigan.
TIP: The wheel soars to heights up to 200 feet. So, if a fear of heights petrifies you, you may want to wait for your elevation-tolerant travel companions at the ground level.
8. Take a Lake Michigan Cruise
If you long to expand your architecture tour and learn more about Chicago and the fifth-largest lake in the world by surface area, consider booking a Lake Michigan boat ride.
The excursions range in duration, time of the day, and the intimacy of experience. You can book a regular session and share a ride with a dozen or more strangers. For an intimate experience, seek a private Lake Michigan sailing escapade that passes by Chicago’s iconic landmarks and enhances your day trip with the city’s outstanding sights.
9. Leave Chicago and Spend a Day in Indiana Dunes National Park
Located roughly 40 miles (45 minutes) southeast of the city, Indiana Dunes National Park is one of the best places to visit when you crave a change of scenery. The area is famous for its diverse terrains. From sandy shoreline to wetlands, prairies, sand dunes, and forests, it enhances your day trip from Chicago with hiking, biking, fishing, swimming, and wildlife watching all year round.
