Chicago itinerary: 3 days for a first trip
Three days in Chicago for a first trip, one part of downtown at a time: Millennium Park, the Bean, the Art Institute and the Cultural Center's Tiffany dome, ending at the Chicago Theatre marquee; Grant Park, Buckingham Fountain, the Field Museum and Shedd Aquarium, then sunset from Willis Tower; and the Riverwalk, the DuSable Bridge, the Magnificent Mile, Navy Pier and the view from 360 CHICAGO.
Every stop sits on one map, colored by day, so you can see how close the Loop, the lakefront and the river are and walk most of it. Want different days or a different pace? Wanderjoy drafts a Chicago plan around your dates on your iPhone, and you can change any stop.
The whole plan on one map
One color per day. Pick a day to see just its route.
How a plan looks in the app
A Chicago trip being revealed in Wanderjoy, pin by pin.
Day by day
Day 1Millennium Park · Loop Chicago
Millennium Park9:00 AM
Start early to walk through the gardens and see the outdoor art before the midday crowds.
Cloud Gate (The Bean)9:45 AM
Walk underneath the Bean to see the skyline reflections twist above your head.
Art Institute of Chicago10:30 AM
Allow at least three hours for highlights such as Nighthawks and A Sunday on La Grande Jatte.
Chicago Cultural Center3:00 PM
The Tiffany glass dome is the main reason to step inside.
Chicago Theatre6:00 PM
Photograph the illuminated CHICAGO marquee from State Street.
Day 2Loop Chicago · Grant Park · Museum Campus
Grant Park9:00 AM
Walk the park paths in the morning for open views back toward the Loop skyline.
Buckingham Fountain9:45 AM
The lakefront and skyline views around the fountain are worth the walk year-round.
Field Museum10:30 AM
Leave several hours for the dinosaur galleries, including SUE the Tyrannosaurus rex.
Shedd Aquarium2:30 PM
Leave time outside for the skyline view across the lake.
Willis Tower6:00 PM
Choose a clear day for the longest views from the Skydeck.
Day 3Loop Chicago · Michigan Avenue · Near North
Chicago Riverwalk9:00 AM
Follow the river-level path for close-up views of the bridges and downtown towers.
DuSable Bridge10:30 AM
Stop on the bridge for views of the Wrigley Building, Tribune Tower and the river canyon.
Magnificent Mile11:15 AM
Walk north along Michigan Avenue to see the landmark towers and the historic Water Tower.
Navy Pier2:00 PM
360 CHICAGO5:30 PM
Choose a clear evening for views north along the beaches and south across downtown.
Plan your own Chicago trip
Different dates or a different pace? Wanderjoy drafts a plan around yours.
Get this trip on a map in the app
Tell Wanderjoy your dates and how you like to travel, and it drafts your own Chicago plan on a map.
Questions
- Can I change the plan?
- Yes. Add, edit or reorder stops, switch days around, and keep trip notes next to the plan.
- Can Wanderjoy make a different Chicago plan for me?
- Yes. Give Wanderjoy your dates and how you like to travel, and it drafts a day-by-day Chicago itinerary on a map for you.
