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Chicago Adventure: 5 Days of Exploring the Windy City

Grace Garcia Hurtado

Grace Garcia Hurtado

27 Sep 2023

Embark on a thrilling 5-day journey through Chicago, IL, United States. Discover iconic landmarks like The Chicago Theatre, The Wrigley Building, The Art Institute of Chicago, Buckingham Fountain, Millennium Park, Riverwalk, DuSable Bridge, Skydeck Chicago, Chicago Board of Trade Building, and The Picasso. Experience the vibrant culture, stunning architecture, and rich history of this magnificent city.

Day 1
+

$38

The Chicago Theatre
French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.
8:00 AM - 10:00 AM
$38
8 - 12 min

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Directions

The Wrigley Building
Beloved 1924 addition to the city skyline, whose clock tower stands 425 ft above street level.
10:30 AM - 11:30 AM
Free
Day 2
+

$32

The Art Institute of Chicago
Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
8:00 AM - 11:00 AM
$31
Day 3
+

$0

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
11 - 16 min

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Directions

Millennium Park
24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.
9:30 AM - 11:30 AM
Free
Day 4
+

$0

Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
8:00 AM - 10:00 AM
Free
3 - 4 min

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Directions

DuSable Bridge
Long-standing drawbridge honoring a founder of Chicago & decorated with sculptures & plaques.
10:30 AM - 11:30 AM
Free
Day 5
+

$32

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
8:00 AM - 9:30 AM
$31
5 - 8 min

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Directions

Chicago Board of Trade Building
Art deco skyscraper, once Chicago's tallest, topped with a statue of Roman goddess Ceres.
10:00 AM - 11:00 AM
Free
8 - 12 min

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Directions

The Picasso
Untitled 50-ft., 160-ton Cor-Ten steel sculpture by artist Pablo Picasso, dedicated in 1967.
11:30 AM - 12:30 PM
Free

Budget breakdown: $100 In total

Activities & Food:$100