Only have 24 hours to explore Chicago before a road trip across the United States? The good news is that the city is well suited to a short visit, provided you plan your day carefully. From striking architecture and rooftops to blues, deep dish pizza and panoramic views, here is our ideal itinerary for deciding what to do in Chicago in one day.
Morning: start with Chicago’s essential sights
Millennium Park and Cloud Gate, ‘The Bean’
Begin your Chicago visit at Millennium Park, one of the city’s best-known landmarks. Here you will find the famous Cloud Gate sculpture, better known as The Bean. It is an excellent starting point for discovering downtown and getting an immediate feel for Chicago’s energy.
The Chicago Riverwalk and landmark architecture
Continue to the Chicago Riverwalk, a pleasant promenade along the river. It is also one of the best places to admire Chicago’s architecture, including landmark buildings such as the Wrigley Building, Tribune Tower and Marina City.
For anyone wondering what to do in Chicago on a first visit, this walk is essential: it helps explain why the city is considered one of the world’s capitals of modern architecture.
The Loop District and the Chicago Theatre
Spend the rest of the morning in the Loop District, Chicago’s historic and financial heart. Discover the famous elevated train tracks, State Street and the iconic Chicago Theatre. It is an essential stop on a first visit to Chicago.
Lunchtime: choose a classic diner or a rooftop
After a morning of walking, choose between skyline views at Cindy’s Rooftop and the classic American diner atmosphere at Lou Mitchell’s. Plan your stop around your chosen venue’s opening times.
Cindy’s Rooftop
Cindy’s Rooftop is an excellent place for lunch or a drink, with beautiful views of Millennium Park and Lake Michigan. The atmosphere is elegant yet approachable.
Lou Mitchell’s: a first stop in the history of Route 66
Before heading west on Route 66, we recommend a stop at Lou Mitchell’s, one of Chicago’s institutions most closely associated with this legendary road. Founded in 1923, three years before Route 66 was established, the diner was already welcoming travellers when the first ‘Mother Road’ signs appeared on Jackson Boulevard. Its position on this historic route made it an iconic stop for people leaving Chicago for Los Angeles. Here you will find an America of counters, booths and hearty breakfasts: eggs, pancakes and coffee to start the day before those first miles. Much of the diner’s 1949 decor survives, including its neon sign and counters, and it has been listed on the National Register of Historic Places since 2006. Taking a seat here introduces you to an essential part of travelling Route 66: family-run restaurants where locals and travellers meet over a meal. Head to 565 W. Jackson Boulevard, near Union Station, for breakfast or an early lunch. Plan to arrive before 2 pm and check the opening days: the restaurant is currently closed on Mondays and Tuesdays.
Afternoon: what to do in Chicago after lunch
Devote the afternoon to exploring the city at your own pace. Depending on your interests, several options can round out your Chicago visit.
- Walk along Lake Michigan
- Go shopping on the Magnificent Mile
- Explore Grant Park
- Take an architectural cruise on the Chicago River
- Visit a museum if the weather is uncooperative, which can happen: Chicago is still Chicago
Buddy Guy’s Legends: an evening of blues in Chicago
If you still have time in the evening, Buddy Guy’s Legends is a must. Founded by Buddy Guy, this blues club is one of the iconic venues on Chicago’s music scene. Admission starts at around $15, depending on the programme.
Late afternoon: sunset at the 360 Chicago Observation Deck
To finish your day, head up to the 360 Chicago Observation Deck on the 94th floor of the building formerly known as the John Hancock Center. It offers some of the city’s finest views.
Sunset is the ideal time to visit. Golden light falls across the skyscrapers, Lake Michigan and the whole skyline. The experience can include a signature cocktail at the bar on the 94th floor.
For travellers looking for an extra thrill, the Tilt Experience lets you lean out over the city from a glass platform. It is optional, payable on site and probably best avoided if you already think a fast lift is a risky activity.
Try deep dish pizza: a Chicago essential
No discussion of things to do in Chicago would be complete without its famous deep dish pizza. This local speciality is closer to a generous savoury pie than a traditional Italian pizza.
Giordano’s
Giordano’s is a classic place to try it. The crust is thick, the cheese plentiful and the tomato sauce generous. It is filling, very American and just right after a day of walking.
Recommended address:
Giordano’s – 223 W Jackson Blvd, Chicago, IL 60606
Giordano’s – 223 W Jackson Blvd, Chicago, IL 60606
Our suggested itinerary for 24 hours in Chicago
Here is a simple way to organise your day:
- Morning: Millennium Park, Cloud Gate, the Riverwalk and the Loop District
- Lunchtime: an early lunch at Lou Mitchell’s before 2 pm on its opening days, or lunch with a view at Cindy’s Rooftop
- Afternoon: time to explore the Magnificent Mile, Grant Park or the Lake Michigan waterfront
- Late afternoon: sunset at the 360 Chicago Observation Deck
- Evening: deep dish pizza or a blues show at Buddy Guy’s Legends
Visit Chicago with Planet Ride
If you would like to enjoy Chicago without spending time on the arrangements, we offer two extensions designed to complement a holiday or road trip in the United States.
Chicago Essentials: discover the city at a glance
This extension is ideal for a first visit to Chicago. It includes a night in a downtown hotel, a walking tour with a French-speaking guide, admission to the 360 Chicago Observation Deck with a cocktail, and a reservation at a restaurant with panoramic views.
The Midwest Getaway
To extend the experience, the Midwest Getaway extension takes your exploration further into the region around Chicago.
What should you do in Chicago in 24 hours?
One day in Chicago already offers a complete experience: architecture, the skyline, Lake Michigan, a rooftop, live music and local food. On a first visit, the key is to stay downtown and organise your stops around the Loop, the Riverwalk, Millennium Park and the 360 Chicago Observation Deck.
Whether you are passing through before a road trip, a Route 66 journey or a Midwest getaway, Chicago clearly deserves at least 24 hours of your time.
Whether you are passing through before a road trip, a Route 66 journey or a Midwest getaway, Chicago clearly deserves at least 24 hours of your time.