Background
Trip Planner Logo

Discover the Vibrant City of Chicago: An 11-Day Adventure

Alberto Montano

Alberto Montano

27 Sep 2023

Embark on an unforgettable journey through the iconic landmarks and hidden gems of Chicago. From the breathtaking views at 360 CHICAGO to the mesmerizing Cloud Gate in Millennium Park, this itinerary will immerse you in the vibrant culture and rich history of the Windy City.

Trip to Chicago

Day 1
+

$125

·

$ 10

DuSable Bridge
Long-standing drawbridge honoring a founder of Chicago & decorated with sculptures & plaques.
8:00 AM - 9:00 AM
•
Free
7 - 9 min

~

Directions

360 CHICAGO
Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.
9:30 AM - 11:00 AM
•
$125
Day 2
+

$0

Jackson (Andrew) Park
540-plus-acre city park featuring a beach, gardens & indoor/outdoor fitness facilities.
8:00 AM - 10:00 AM
•
Free
Day 3
+

$200

Shedd Aquarium
State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.
8:00 AM - 11:00 AM
•
$200
Day 4
+

$0

Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
8:00 AM - 10:00 AM
•
Free
Day 5
+

$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
2 - 3 min

~

Directions

Cloud Gate
Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.
10:30 AM - 11:30 AM
•
Free
Day 6
+

$125

·

$ 10

The Wrigley Building
Beloved 1924 addition to the city skyline, whose clock tower stands 425 ft above street level.
8:00 AM - 9:00 AM
•
Free
11 - 14 min

~

Directions

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
9:30 AM - 11:00 AM
•
$125
Day 7
+

$0

Lincoln Park Zoo
Small, free zoo with lions, primates, reptiles, a children's area & an interactive farm exhibit.
8:00 AM - 10:00 AM
•
Free
Day 8
+

$0

Grant Park
312-acre centerpiece of Downtown housing some of the city's busiest attractions.
8:00 AM - 10:00 AM
•
Free
Day 9
+

$150

The Chicago Theatre
French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.
8:00 AM - 10:00 AM
•
$150
Day 10
+

$100

Brookfield Zoo
Lions, tigers, dolphins & more frolic in natural indoor & outdoor settings at this wildlife park.
8:00 AM - 12:00 PM
•
$100
Day 11
+

$0

Budget breakdown: $720 In total

Activities & Food:$700
Transport:$20