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Discover the Best of Chicago in 8 Days

Milena Arias

Milena Arias

8 Oct 2023

Embark on an unforgettable 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
+

$99

·

$ 5

Navy Pier
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
8:00 AM - 10:00 AM
•
$63
11 - 14 min

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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
5 - 8 min

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Directions

Wildberry Pancakes & Cafe
1:00 PM - 2:30 PM
•
$36
Day 2
+

$87

·

$ 5

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
8:00 AM - 9:30 AM
•
$63
9 - 11 min

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Directions

Millennium Park
24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.
10:00 AM - 12:00 PM
•
Free
6 - 9 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.
1:00 PM - 2:30 PM
•
$24
Day 3
+

$87

Field Museum
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
8:00 AM - 11:00 AM
•
$63
12 - 18 min

~

Directions

Victory Tap
Serving traditional Italian food since 1956 with a passion for traditional Italian dishes has created our fine menu of tried and true classics sure to impress anyones pallet.
1:00 PM - 2:30 PM
•
$24
Day 4
+

$74

Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
8:00 AM - 10:00 AM
•
Free
14 - 21 min

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Directions

Museum Of Contemporary Art Chicago
Downtown museum showcasing post-World War II paintings, sculptures, photos, videos & performances.
10:30 AM - 12:00 PM
•
$38
4 - 5 min

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Directions

Cafecito
1:00 PM - 2:30 PM
•
$36
Day 5
+

$48

·

$ 10

Grant Park
312-acre centerpiece of Downtown housing some of the city's busiest attractions.
8:00 AM - 10:00 AM
•
Free
17 - 21 min

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Directions

Garfield Park Conservatory - Reservations Required
184-acre park with a swimming pool, fishing lagoon, athletic fields & tennis courts.
10:30 AM - 12:00 PM
•
Free
7 - 9 min

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Directions

Rootstock Wine & Beer Bar
1:00 PM - 2:30 PM
•
$48
Day 6
+

$40

Museum Campus
57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.
8:00 AM - 11:00 AM
•
Free
11 - 16 min

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Directions

Eleven City Diner
1:00 PM - 2:30 PM
•
$40
Day 7
+

$109

·

$ 5

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
5 - 6 min

~

Directions

Plein Air Cafe & Eatery
1:00 PM - 2:30 PM
•
$34
Day 8
+

$36

·

$ 5

Jackson (Andrew) Park
540-plus-acre city park featuring a beach, gardens & indoor/outdoor fitness facilities.
8:00 AM - 10:00 AM
•
Free
7 - 9 min

~

Directions

The Promontory
1:00 PM - 2:30 PM
•
$36

Budget breakdown: $608 In total

Activities & Food:$578
Transport:$30