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Chicago Adventure: 4-Day Itinerary

Jorge Massieu

Jorge Massieu

18 Oct 2023

Embark on an exciting 4-day journey through the vibrant city of Chicago. Explore iconic landmarks, indulge in delicious cuisine, and immerse yourself in the rich culture of the Windy City.

Trip to Chicago

Day 1
+

$26

·

$ 5

Courtyard by Marriott Chicago Downtown/Magnificent Mile

Depart from your stay 🏨

6 - 9 min

~

Directions

Courtyard by Marriott Chicago Downtown/Magnificent Mile
Modern hotel with a bistro restaurant, an indoor pool & a cozy lobby sitting area, plus free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
12 - 15 min

~

Directions

City Gallery in the Historic Water Tower
Chicago-focused gallery, specializing in photos, inside a 19th-century Gothic limestone landmark.
8:00 AM - 9:00 AM
•
Free
11 - 16 min

~

Directions

The Merchandise Mart
Huge building featuring high-end home design & furniture showrooms, plus a lineup of trade shows.
9:30 AM - 10:30 AM
•
Free
8 - 11 min

~

Directions

The Picasso
Untitled 50-ft., 160-ton Cor-Ten steel sculpture by artist Pablo Picasso, dedicated in 1967.
11:00 AM - 12:00 PM
•
Free
5 - 8 min

~

Directions

Cloud Gate
Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.
12:30 PM - 1:30 PM
•
Free
Wildberry Pancakes & Cafe
7:00 PM - 8:30 PM
•
$26
Courtyard by Marriott Chicago Downtown/Magnificent Mile
Modern hotel with a bistro restaurant, an indoor pool & a cozy lobby sitting area, plus free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
Day 2
+

$123

·

$ 5

Courtyard by Marriott Chicago Downtown/Magnificent Mile

Depart from your stay 🏨

9 - 11 min

~

Directions

Courtyard by Marriott Chicago Downtown/Magnificent Mile
Modern hotel with a bistro restaurant, an indoor pool & a cozy lobby sitting area, plus free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
3 - 4 min

~

Directions

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
8 - 12 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
4 - 5 min

~

Directions

The Chicago Theatre
French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.
12:00 PM - 2:00 PM
•
$75
Roti Modern Mediterranean
By Millenium Park at Lake and Michigan, Downtown Chicago restaurant Roti Modern Mediterranean offers a menu of deliciously fresh salads, bowls, & pitas
7:00 PM - 8:30 PM
•
$48
Courtyard by Marriott Chicago Downtown/Magnificent Mile
Modern hotel with a bistro restaurant, an indoor pool & a cozy lobby sitting area, plus free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
Day 3
+

$98

·

$ 10

Courtyard by Marriott Chicago Downtown/Magnificent Mile

Depart from your stay 🏨

5 - 8 min

~

Directions

Courtyard by Marriott Chicago Downtown/Magnificent Mile
Modern hotel with a bistro restaurant, an indoor pool & a cozy lobby sitting area, plus free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
3 - 4 min

~

Directions

Tribune Tower
Neo-Gothic skyscraper influenced by Rouen Cathedral & decorated with rocks from world landmarks.
8:00 AM - 9:00 AM
•
Free
24 - 29 min

~

Directions

DuSable Bridge
Long-standing drawbridge honoring a founder of Chicago & decorated with sculptures & plaques.
9:30 AM - 10:30 AM
•
Free
32 - 39 min

~

Directions

Frederick C. Robie House
Notable 1910 Prairie-style house designed by Frank Lloyd Wright, offering tours 5 days a week.
11:00 AM - 12:00 PM
•
$50
6 - 9 min

~

Directions

Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
12:30 PM - 2:30 PM
•
Free
Roti Modern Mediterranean
By Millenium Park at Lake and Michigan, Downtown Chicago restaurant Roti Modern Mediterranean offers a menu of deliciously fresh salads, bowls, & pitas
7:00 PM - 8:30 PM
•
$48
Courtyard by Marriott Chicago Downtown/Magnificent Mile
Modern hotel with a bistro restaurant, an indoor pool & a cozy lobby sitting area, plus free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
Day 4
+

$201

·

$ 15

Courtyard by Marriott Chicago Downtown/Magnificent Mile

Depart from your stay 🏨

53 - 64 min

~

Directions

Courtyard by Marriott Chicago Downtown/Magnificent Mile
Modern hotel with a bistro restaurant, an indoor pool & a cozy lobby sitting area, plus free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
27 - 33 min

~

Directions

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
1 - 2 min

~

Directions

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
10:00 AM - 11:30 AM
•
$63
8 - 11 min

~

Directions

Willis Tower
Iconic, 110-story skyscraper featuring expansive views of Chicago from its 103rd-story Skydeck.
12:00 PM - 2:00 PM
•
$63
Garrett Popcorn Shops
7:00 PM - 8:30 PM
•
$26
Courtyard by Marriott Chicago Downtown/Magnificent Mile
Modern hotel with a bistro restaurant, an indoor pool & a cozy lobby sitting area, plus free Wi-Fi.
7:30 AM - 7:30 AM
•
Free

Budget breakdown: $483 In total

Activities & Food:$448
Transport:$35