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 — First-Time Trip in 5 Days
5 days30 stopsChicago
Starter 5-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.
09:00 - 10:1575 minAttraction
The Wrigley Building
400-410 N Michigan Ave, Chicago, IL 60611
Beloved 1924 addition to the city skyline, whose clock tower stands 425 ft above street level.
Drive (over walking limit) · 12 min · 3.3 km
10:27 - 11:2760 minAttraction
Shedd Aquarium
1200 S DuSable Lake Shore Dr, Chicago, IL 60605
State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.
Walk (under walking limit) · 3 min · 220 m
11:30 - 13:30120 minMuseum
The Museum Campus
337 E Randolph St, Chicago, IL 60601
57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.
Walk (under walking limit) · 11 min · 820 m
13:41 - 14:2645 minAttraction
Adler Planetarium
1300 S DuSable Lake Shore Dr, Chicago, IL 60605
Interactive exhibits & high-tech sky shows entertain stargazers, lakefront views are a bonus.
Walk (under walking limit) · 20 min · 1.5 km
14:46 - 15:2135 minNature
Grant Park
Chicago, IL
312-acre centerpiece of Downtown housing some of the city's busiest attractions.
Walk (under walking limit) · 13 min · 990 m
15:34 - 16:4470 minMuseum
Field Museum
1400 S Lake Shore Dr, Chicago, IL 60605
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
09:00 - 10:55115 minTourist Attraction
Chicago Harbor Lighthouse
Chicago Harbor, Chicago, IL 60603, USA
Chicago Harbor Lighthouse is an Attraction in Chicago.
Drive (over walking limit) · 17 min · 5.4 km
11:12 - 12:1765 minMuseum
Chicago History Museum
1601 N Clark St, Chicago, IL 60614, USA
Photos, artifacts, newsreels & dioramas bring to life historical events, architecture & culture.
Walk (under walking limit) · 16 min · 1.3 km
12:33 - 14:0390 minTourist Attraction
Lincoln Park Zoo
Chicago, IL 60614, USA
Small, free zoo with lions, primates, reptiles, a children's area & an interactive farm exhibit.
Walk (under walking limit) · 18 min · 1.4 km
14:21 - 15:1655 minLodging
The Neighborhood Hotel Lincoln Park
2616 N Clark St, Chicago, IL 60614, USA
The Neighborhood Hotel Lincoln Park is a Landmark in Chicago.
Walk (under walking limit) · 15 min · 1.1 km
15:31 - 16:0130 minPark
Oz Park
2021 N Burling St, Chicago, IL 60614, USA
Oz-themed playground/park with statues of the Tin Man, Scarecrow, Cowardly Lion & Dorothy.
Drive (over walking limit) · 22 min · 7.6 km
16:23 - 17:3875 minLodging
The Neighborhood Hotel Little Italy
1431 W Taylor St, Chicago, IL 60607, USA
The Neighborhood Hotel Little Italy is a Landmark in Chicago.
09:00 - 10:1575 minPark
Millennium Park
Chicago, IL 60602, USA
24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.
Walk (under walking limit) · 22 min · 1.7 km
10:37 - 11:4265 minFood
Chicago French Market
131 N Clinton St, Chicago, IL 60661, USA
European-inspired indoor food market for grab-&-go meals, fresh produce & specialty kiosks.
Walk (under walking limit) · 11 min · 860 m
11:53 - 13:1380 minPark
The Green at 320 Park
320 S Canal St, Chicago, IL 60606, USA
The Green at 320 Park is a Nature in Chicago.
Drive (over walking limit) · 13 min · 3.9 km
13:26 - 14:1145 minPark
Milton Lee Olive Park
E Ohio St, Chicago, IL 60611, USA
Secluded urban oasis on the water with city skyline views, serene paths & circular fountains.
Drive (over walking limit) · 13 min · 3.7 km
14:24 - 14:5935 minPark
Lincoln Park
500-5700 N Lake Shore Dr, Chicago, IL 60614, USA
Expansive outdoor urban refuge containing its own zoo, conservatory, theater, museums & playgrounds.
Drive (over walking limit) · 12 min · 3.6 km
15:11 - 16:2675 minFood
Gangnam Market
1001 W Chicago Ave, Chicago, IL 60642, USA
Gangnam Market is a Shopping in Chicago.