Itinerary · Chicago · United States
One day in Chicago
A day-by-day plan grouped by neighbourhood, so you spend your time seeing Chicago, not crossing it.
Updated By the AMZBooking editorial team
Quick answer
One day is a taster: the plan below covers the essentials, but most visitors want 4. Day 1: Millennium Park and Cloud Gate and Art Institute of Chicago. Base yourself in The Loop.
Key facts
- Days
- 1
- Sights covered
- 5
- Day trips
- None
- Best base
- The Loop
- Book ahead
- Willis Tower Skydeck and The Second City
Day by day
Day 1: Millennium Park and Cloud Gate and Art Institute of Chicago
Millennium Park and Cloud Gate, Art Institute of Chicago, Willis Tower Skydeck and Chicago Riverwalk, then The Second City in the evening.
Morning
Millennium Park and Cloud Gate
See the Bean early in the morning before the crowds, then cross Gehry's winding BP Bridge to Maggie Daley Park. Allow 1–2 hours.
Late morning
Art Institute of Chicago
Start with the Impressionists on the second floor before tour groups arrive, then take the Modern Wing's Nichols Bridgeway straight into Millennium Park. Allow 3–4 hours.
Lunch
Lunch: Deep-dish pizza
Pizzeria Uno in River North, where the style is said to have started in 1943, plus Lou Malnati's, Giordano's and Pequod's, known for its caramelised cheese crust.
Afternoon
Willis Tower Skydeck
Check the visibility before buying; low cloud can hide the view completely, and a late-afternoon visit gives you daylight and sunset in one ticket. Allow 1.5–2 hours.
Late afternoon
Chicago Riverwalk
Look into the McCormick Bridgehouse & Chicago River Museum in the DuSable Bridge tower to see the gears that raise the bridge; it opens seasonally. Allow 1–2 hours.
Evening
The Second City
Stay after the late show for the improv set, where the cast tests new material from audience suggestions.
Before you go
- Willis Tower Skydeck: Queues for The Ledge can be long in summer; timed tickets bought online shorten the wait.
- The Second City: Weekend shows sell out; book a few days ahead.
If it rains
- Swap in Field Museum (Museum Campus): Arrive at opening and do the Field in the morning; the Shedd is a five-minute walk away for the afternoon.
- Swap in Shedd Aquarium (Museum Campus): Walk the lakefront path from the Shedd to the Adler Planetarium afterwards for the classic skyline photo.
- Swap in Adler Planetarium (Museum Campus): Even if you skip the museum, walk out to the Adler around sunset for the view back across the harbour to downtown.
Where to stay for this itinerary
$$$ · Best for first-timers, culture and families
The Loop
Elevated L tracks, skyscraper canyons, Millennium Park and the State Street theatres
Pace and daylight
The sights in this plan add up to roughly 9–12 hours of visiting over one day, before meals and getting between them. Daylight runs from about 9.1 hours in December to 15.2 hours in June, so in winter start early and keep museums for the afternoon.
Getting between stops: Metro. The L (elevated and subway trains) reaches most visitor areas: the Blue Line links O'Hare with Wicker Park and the Loop, the Red Line runs past Wrigley Field and Chinatown, and the Brown Line gives elevated views around the Loop.
More or fewer days
Questions travellers ask
+Is one day enough in Chicago?
One day is a taster: the plan below covers the essentials, but most visitors want 4. How many days Chicago needs.
+What should I book before visiting Chicago?
Willis Tower Skydeck and The Second City.