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8 Days in the Windy City

Tomatti 20

Tomatti 20

15 Dec 2023

Embark on an unforgettable journey through the vibrant streets of Chicago. Immerse yourself in art, architecture, and culture as you explore iconic landmarks and hidden gems. From towering skyscrapers to world-class museums, this itinerary promises an exhilarating adventure in the Windy City.

Trip to Chicago

Day 1Urban Wonders and Artistic Delights
+

$114

Richard J. Daley Center
Daley Center's open-air courtyard with a huge Picasso sculpture, benches & seasonal farmer's market.
8:00 AM - 9:00 AM
•
Free
5 - 8 min

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Directions

Museum of Illusions Chicago
Immersive rooms with optical illusions & holograms designed to deceive the eye, popular for photos.
9:30 AM - 11:00 AM
•
$50
7 - 10 min

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Directions

The Art Institute of Chicago
Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
11:30 AM - 2:30 PM
•
$64
Day 2Architectural Marvels and Cultural Treasures
+

$50

·

$ 15

Frank Lloyd Wright Home & Studio
Home & studio of the famous architect, with guided tours focused on his early career.
8:00 AM - 9:30 AM
•
$50
22 - 27 min

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Directions

Humboldt (Alexander Von) Park
Suburban recreational area with soccer & baseball fields, tennis courts & playgrounds, plus a beach.
10:00 AM - 12:00 PM
•
Free
22 - 27 min

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Directions

National Museum of Mexican Art
Some 18,000 paintings, photographs, sculptures & more are housed at this art museum.
12:30 PM - 2:00 PM
•
Free
15 - 18 min

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Directions

Monadnock Building
Built in 1893, this notable site was at the time the largest office building in the world.
2:30 PM - 3:30 PM
•
Free
8 - 12 min

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Directions

Museum of Contemporary Photography
Museum offering programs & events, with a U.S.-focused permanent collection & rotating exhibits.
4:00 PM - 5:00 PM
•
Free
Day 3Science, Art, and Creativity
+

$75

·

$ 10

Museum of Science and Industry, Chicago
Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.
8:00 AM - 12:00 PM
•
$75
6 - 8 min

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Directions

Hyde Park Art Center
Nonprofit visual arts center exhibiting work by emerging or under-recognized contemporary artists.
12:30 PM - 2:00 PM
•
Free
11 - 14 min

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Directions

Smart Museum of Art
Museum specializing in Asian, European, Contemporary & Modern Art, with over 12,000 objects.
2:30 PM - 4:00 PM
•
Free
Day 4Nature's Oasis and Historical Insights
+

$113

·

$ 15

Lincoln Park Conservatory
Thousands of exotic plants in an 1890 glass structure, plus outdoor gardens & fountains.
8:00 AM - 9:00 AM
•
Free
6 - 8 min

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Directions

Chicago History Museum
Photos, artifacts, newsreels & dioramas bring to life historical events, architecture & culture.
9:30 AM - 11:30 AM
•
$50
6 - 8 min

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Directions

360 CHICAGO
Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.
12:00 PM - 1:30 PM
•
$63
9 - 11 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.
2:00 PM - 3:00 PM
•
Free
8 - 12 min

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Directions

Chicago Cultural Center
Free art & shows in an 1897 Beaux-Arts building with vaulted lobby, mosaics & 2 stained-glass domes.
3:30 PM - 4:30 PM
•
Free
Day 5Parks, Museums, and Chicago's Soul
+

$63

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
12 - 17 min

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Directions

Grant Park
312-acre centerpiece of Downtown housing some of the city's busiest attractions.
10:30 AM - 12:30 PM
•
Free
10 - 15 min

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Directions

Field Museum
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
1:00 PM - 4:00 PM
•
$63
Day 6Sky-High Thrills and Urban Oasis
+

$63

·

$ 15

Willis Tower
Iconic, 110-story skyscraper featuring expansive views of Chicago from its 103rd-story Skydeck.
8:00 AM - 10:00 AM
•
$63
11 - 14 min

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Directions

The Merchandise Mart
Huge building featuring high-end home design & furniture showrooms, plus a lineup of trade shows.
10:30 AM - 11:30 AM
•
Free
14 - 17 min

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Directions

Cloud Gate
Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.
12:00 PM - 1:00 PM
•
Free
4 - 6 min

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Directions

Jay Pritzker Pavilion
Designed by architect Frank Gehry, this bandshell in Millennium Park hosts various musical events.
1:30 PM - 2:30 PM
•
Free
6 - 8 min

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Directions

Milton Lee Olive Park
Secluded urban oasis on the water with city skyline views, serene paths & circular fountains.
3:00 PM - 4:00 PM
•
Free
Day 7Serene Gardens and Iconic Landmarks
+

$88

·

$ 10

Alfred Caldwell Lily Pool
This serene section of Lincoln Park stars a lily pool & also boasts lush landscaping & a pavilion.
8:00 AM - 9:00 AM
•
Free
15 - 18 min

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Directions

DuSable Bridge
Long-standing drawbridge honoring a founder of Chicago & decorated with sculptures & plaques.
9:30 AM - 10:30 AM
•
Free
9 - 14 min

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Directions

Crown Fountain
Public sculpture with 2 50-ft. LED towers & a reflecting pool, by Catalan artist Jaume Plensa.
11:00 AM - 12:00 PM
•
Free
11 - 16 min

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Directions

Buckingham Fountain
Among the world’s largest, Grant Park’s 3-level rococo fountain (1927) offers light & water shows.
12:30 PM - 1:30 PM
•
Free
7 - 9 min

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Directions

Adler Planetarium
Interactive exhibits & high-tech sky shows entertain stargazers, lakefront views are a bonus.
2:00 PM - 5:00 PM
•
$88
Day 8Aquatic Wonders and Theatrical Grandeur
+

$175

·

$ 5

Shedd Aquarium
State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.
8:00 AM - 11:00 AM
•
$100
11 - 14 min

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Directions

The Chicago Theatre
French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.
11:30 AM - 1:30 PM
•
$75

Budget breakdown: $809 In total

Activities & Food:$739
Transport:$70