09:00 - 10:55115 minMuseum
Museum Of Contemporary Art Chicago
East Chicago Avenue, Chicago, IL, USA
Downtown museum showcasing post-World War II paintings, sculptures, photos, videos & performances.
BackAPR 2026 · TEMPLATE ITINERARY
Chicago — Classic City Break in 2 Days
2 days12 stopsChicago
Starter 2-day Chicago itinerary with clustered routing, paced dwell times, and realistic travel legs.
DATES FLEXIBLE
Trip details
A quick planning snapshot before you drop into the full day-by-day itinerary.
Itinerary
Day-by-day itinerary
Browse the full structure first, then save it into your own account when you're ready to customise the route, pacing, and stop mix.
Walk (under walking limit) · 12 min · 900 m
11:07 - 12:0760 minAttraction
Tribune Tower
435 N Michigan Ave, Chicago, IL 60611
Neo-Gothic skyscraper influenced by Rouen Cathedral & decorated with rocks from world landmarks.
Walk (under walking limit) · 3 min · 180 m
12:10 - 13:50100 minAttraction
DuSable Bridge
333 N Michigan Ave, Chicago, IL 60601
Long-standing drawbridge honoring a founder of Chicago & decorated with sculptures & plaques.
Walk (under walking limit) · 10 min · 780 m
14:00 - 14:5050 minAttraction
Cloud Gate
201 E Randolph St, Chicago, IL 60602
Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.
Walk (under walking limit) · 5 min · 370 m
14:55 - 15:2025 minNature
Maggie Daley Park
337 E Randolph St, Chicago, IL 60601
Popular recreational area with winter ice skating, a climbing wall & playground equipment.
Walk (under walking limit) · 11 min · 840 m
15:31 - 16:3160 minAttraction
Chicago Riverwalk
Chicago, IL 60601
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
09:00 - 10:2585 minAttraction
Willis Tower
233 S Wacker Dr, Chicago, IL 60606
Iconic, 110-story skyscraper featuring expansive views of Chicago from its 103rd-story Skydeck.
Walk (under walking limit) · 15 min · 1.2 km
10:40 - 11:4060 minAttraction
THE MART
222 W Merchandise Mart Plaza, Chicago, IL 60654
Huge building featuring high-end home design & furniture showrooms, plus a lineup of trade shows.
Walk (under walking limit) · 15 min · 1.2 km
11:55 - 13:3095 minAmusement Park
Color Factory Chicago
233 S Wacker Dr Lower Level 2, Chicago, IL 60606, USA
Color Factory Chicago is an Attraction in Chicago.
Walk (under walking limit) · 16 min · 1.3 km
13:46 - 14:4660 minMuseum
The Art Institute of Chicago
111 S Michigan Ave, Chicago, IL 60603
Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
Walk (under walking limit) · 16 min · 1.3 km
15:02 - 15:4240 minShopping
Skydeck Chicago
233 S Wacker Dr, Chicago, IL 60606
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
Walk (under walking limit) · 21 min · 1.6 km
16:03 - 16:5350 minAttraction
Clarence F. Buckingham Memorial Fountain
301 S Columbus Dr, Chicago, IL 60605
Among the world’s largest, Grant Park’s 3-level rococo fountain (1927) offers light & water shows.