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4 Days in the Windy City

Maureen Daley

Maureen Daley

26 Nov 2023

Experience the vibrant city of Chicago in just 4 days! From iconic landmarks to cultural hotspots, this itinerary will take you on an unforgettable journey through the heart of the Midwest.

Trip to Chicago

Day 1Pier, Art, Science & Plein Air
+

$152

·

$ 23

Navy Pier
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
8:00 AM - 10:00 AM
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Free
9 - 11 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
14 - 17 min

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Directions

Museum of Science and Industry, Chicago
Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.
12:00 PM - 4:00 PM
•
$113
5 - 6 min

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Directions

Plein Air Cafe & Eatery
7:00 PM - 8:30 PM
•
$39
Day 2Masterpieces, Parks, Aquarium & Tap
+

$303

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
•
$96
9 - 14 min

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Directions

Grant Park
312-acre centerpiece of Downtown housing some of the city's busiest attractions.
11:30 AM - 1:30 PM
•
Free
13 - 20 min

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Directions

Shedd Aquarium
State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.
2:00 PM - 5:00 PM
•
$150
16 - 23 min

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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.
7:00 PM - 8:30 PM
•
$57
Day 3History, Fountain, Park, Riverwalk & Roti
+

$260

·

$ 15

Field Museum
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
8:00 AM - 11:00 AM
•
$94
11 - 14 min

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Directions

Willis Tower
Iconic, 110-story skyscraper featuring expansive views of Chicago from its 103rd-story Skydeck.
No time set
•
$94
0
Buckingham Fountain
Among the world’s largest, Grant Park’s 3-level rococo fountain (1927) offers light & water shows.
11:30 AM - 12:30 PM
•
Free
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.
1:00 PM - 3:00 PM
•
Free
11 - 16 min

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Directions

Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
3:30 PM - 5:30 PM
•
Free
10 - 15 min

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Directions

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
•
$72
6 - 9 min

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Directions

Budget breakdown: $752 In total

Activities & Food:$714
Transport:$38