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Discover the Best of Chicago: 5-Day Itinerary

Yicaury Manzueta Otaño

Yicaury Manzueta Otaño

22 Oct 2023

Embark on an unforgettable journey through the vibrant city of Chicago with this 5-day itinerary. Explore iconic landmarks, indulge in delicious cuisine, and immerse yourself in the rich culture of the Windy City.

Trip to Chicago

Day 1
+

$71

Osaka Sushi Express & Fresh Fruit Smoothies
7:30 AM - 8:30 AM
•
$8
8 - 11 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.
9:00 AM - 10:00 AM
•
Free
9 - 14 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.
10:30 AM - 1:30 PM
•
$32
6 - 9 min

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Directions

Garrett Popcorn Shops
2:00 PM - 3:30 PM
•
$18
5 - 8 min

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Directions

Cafecito
7:00 PM - 8:30 PM
•
$13
Day 2
+

$71

·

$ 5

Carnitas Uruapan
A Foodie Favorite. We've been serving up the Best Authentic Carnitas in Chicago since 1975!
7:30 AM - 8:30 AM
•
$15
5 - 8 min

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Directions

National Museum of Mexican Art
Some 18,000 paintings, photographs, sculptures & more are housed at this art museum.
9:00 AM - 10:30 AM
•
Free
15 - 18 min

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Directions

WNDR Museum
Multi-sensory, contemporary installations by artists including Yayoi Kusama.
11:00 AM - 12:30 PM
•
$31
16 - 20 min

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Directions

Wildberry Pancakes & Cafe
1:00 PM - 2:30 PM
•
$12
5 - 8 min

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Directions

Millennium Park
24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.
2:30 PM - 4:30 PM
•
Free
6 - 9 min

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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.
1:30 PM - 3:00 PM
•
$12
Day 3
+

$81

·

$ 3

B'Gabs
Raw, vegan, gluten-free, soy-free, peanut-free, smoothie bar, juice bar, herbs, tea, essential oils
7:30 AM - 8:30 AM
•
$7
8 - 11 min

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Directions

Museum of Science and Industry, Chicago
Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.
9:00 AM - 1:00 PM
•
$38
20 - 24 min

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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.
1:30 PM - 3:00 PM
•
$12
6 - 9 min

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Directions

Cloud Gate
Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.
3:00 PM - 4:00 PM
•
Free
6 - 9 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
•
$24
Day 4
+

$75

·

$ 3

Yolk
YOLK, created by founder Taki Kastanis in 2006, has evolved into Chicago's #1 breakfast hot spot. Follow us on Twitter and Instagram @EatYolk #EatYolk
7:30 AM - 8:30 AM
•
$12
10 - 15 min

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Directions

Museum Campus
57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.
9:00 AM - 12:00 PM
•
Free
8 - 10 min

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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.
12:30 PM - 2:00 PM
•
$18
10 - 15 min

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Directions

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
2:00 PM - 3:30 PM
•
$31
9 - 14 min

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Directions

Hogsalt - Small C
7:00 PM - 8:30 PM
•
$13
Day 5
+

$98

·

$ 5

Ranalli's Lincoln Park
The Ranalli's family-owned business has been keeping Chicagoans well-fed for over 30 years. Starting on Lincoln Avenue in the 1970s, Ranalli's legendary food and around the world beer list, along with its famous outdoor patio, has become a favorite of both locals and tourists alike.
7:30 AM - 8:30 AM
•
$10
8 - 12 min

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Directions

Lincoln Park Zoo
Small, free zoo with lions, primates, reptiles, a children's area & an interactive farm exhibit.
9:00 AM - 11:00 AM
•
Free
19 - 23 min

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Directions

Adler Planetarium
Interactive exhibits & high-tech sky shows entertain stargazers, lakefront views are a bonus.
11:30 AM - 2:30 PM
•
$44
11 - 14 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.
3:00 PM - 4:30 PM
•
$24
10 - 15 min

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Directions

Grant Park Bistro
7:00 PM - 8:30 PM
•
$20

Budget breakdown: $409 In total

Activities & Food:$394
Transport:$15