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A Week in Chicago: Explore the Best of the Windy City

Elena Castro

Elena Castro

16 Oct 2023

Embark on a thrilling 7-day journey through Chicago, IL, United States. Discover iconic landmarks, indulge in delicious cuisine, and immerse yourself in the vibrant culture of the Windy City.

Trip to Chicago

Day 1
+

$93

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
5 - 8 min

~

Directions

Wildberry Pancakes & Cafe
1:00 PM - 2:30 PM
•
$54
4 - 6 min

~

Directions

Sweetgreen
Fresh salads, plates + grain bowls available for pickup and delivery every day, made in-house from scratch, using whole produce delivered that morning.
7:00 PM - 8:30 PM
•
$39
Day 2
+

$221

·

$ 8

The Chicago Theatre
French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.
8:00 AM - 10:00 AM
•
$113
6 - 8 min

~

Directions

Buckingham Fountain
Among the world’s largest, Grant Park’s 3-level rococo fountain (1927) offers light & water shows.
10:30 AM - 11:30 AM
•
Free
10 - 15 min

~

Directions

Grant Park Bistro
1:00 PM - 2:30 PM
•
$36
11 - 16 min

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Directions

Garrett Popcorn Shops
7:00 PM - 8:30 PM
•
$72
Day 3
+

$202

Navy Pier
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
8:00 AM - 10:00 AM
•
$94
11 - 16 min

~

Directions

Cupitol Coffee & Eatery
Cupitol is a new all-day​ lounge that brings together the best elements of a restaurant, a bakery, a cafe and an exclusive bar.
1:00 PM - 2:30 PM
•
$36
4 - 6 min

~

Directions

Buona
Quick casual restaurant featuring Original Italian Beef, Pizza, Burgers, Hot Dogs, Sandwiches and Salads
7:00 PM - 8:30 PM
•
$72
Day 4
+

$205

·

$ 8

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

~

Directions

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
10:30 AM - 12:00 PM
•
$94
8 - 11 min

~

Directions

Garrett Popcorn Shops
7:00 PM - 8:30 PM
•
$72
5 - 8 min

~

Directions

Sweetgreen
Fresh salads, plates + grain bowls available for pickup and delivery every day, made in-house from scratch, using whole produce delivered that morning.
7:00 PM - 8:30 PM
•
$39
Day 5
+

$132

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
6 - 9 min

~

Directions

Chicago Pizza & Oven Grinder
1:00 PM - 2:30 PM
•
$72
8 - 12 min

~

Directions

Firecakes Donuts
7:00 PM - 8:30 PM
•
$60
Day 6
+

$226

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
•
$94
7 - 10 min

~

Directions

Cafecito
1:00 PM - 2:30 PM
•
$60
5 - 8 min

~

Directions

Garrett Popcorn Shops
7:00 PM - 8:30 PM
•
$72
Day 7
+

$0

Budget breakdown: $1093 In total

Activities & Food:$1078
Transport:$15