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Discover the Best of Chicago in 5 Days

Alejandra Granada

Alejandra Granada

27 Sep 2023

Experience the vibrant city of Chicago in this exciting 5-day itinerary. Explore iconic landmarks, stunning architecture, and immerse yourself in the rich cultural scene.

Trip to Chicago

Day 1
+

$0

Museum Campus
57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.
8:00 AM - 11:00 AM
•
Free
Day 2
+

$0

Millennium Park
24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.
8:00 AM - 10:00 AM
•
Free
3 - 4 min

~

Directions

Crown Fountain
Public sculpture with 2 50-ft. LED towers & a reflecting pool, by Catalan artist Jaume Plensa.
10:30 AM - 11:30 AM
•
Free
Day 3
+

$0

·

$ 10

Buckingham Fountain
Among the world’s largest, Grant Park’s 3-level rococo fountain (1927) offers light & water shows.
8:00 AM - 9:00 AM
•
Free
6 - 8 min

~

Directions

Chicago Cultural Center
Free art & shows in an 1897 Beaux-Arts building with vaulted lobby, mosaics & 2 stained-glass domes.
9:30 AM - 10:30 AM
•
Free
9 - 11 min

~

Directions

Civic Opera House
North America's 2nd-largest opera venue has over 3,500 seats & houses the Lyric Opera of Chicago.
11:00 AM - 12:30 PM
•
Free
Day 4
+

$0

·

$ 5

Lincoln Park Conservatory
Thousands of exotic plants in an 1890 glass structure, plus outdoor gardens & fountains.
8:00 AM - 9:00 AM
•
Free
7 - 9 min

~

Directions

City Gallery in the Historic Water Tower
Chicago-focused gallery, specializing in photos, inside a 19th-century Gothic limestone landmark.
9:30 AM - 10:30 AM
•
Free
9 - 14 min

~

Directions

The Wrigley Building
Beloved 1924 addition to the city skyline, whose clock tower stands 425 ft above street level.
11:00 AM - 12:00 PM
•
Free
2 - 3 min

~

Directions

DuSable Bridge
Long-standing drawbridge honoring a founder of Chicago & decorated with sculptures & plaques.
12:30 PM - 1:30 PM
•
Free
Day 5
+

$63

·

$ 5

360 CHICAGO
Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.
8:00 AM - 9:30 AM
•
$63
12 - 15 min

~

Directions

Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
10:00 AM - 12:00 PM
•
Free

Budget breakdown: $83 In total

Activities & Food:$63
Transport:$20