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Exploring the Best of Chicago: A 5-Day Adventure

Gabriela Ancheita

Gabriela Ancheita

2 Oct 2023

Embark on a thrilling 5-day journey through the vibrant city of Chicago, experiencing its iconic landmarks, delicious cuisine, and captivating culture.

Trip to Chicago

Day 1
+

$141

·

$ 5

Wildberry Pancakes & Cafe
7:30 AM - 8:30 AM
$16
5 - 8 min

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Directions

Cloud Gate
Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.
9:00 AM - 10:00 AM
Free
5 - 6 min

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Directions

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
10:30 AM - 12:00 PM
$63
8 - 11 min

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Directions

Garrett Popcorn Shops
1:00 PM - 2:30 PM
$36
5 - 8 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.
7:00 PM - 8:30 PM
$26
Day 2
+

$92

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
$30
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
6 - 9 min

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Directions

Chicago Pizza & Oven Grinder
1:00 PM - 2:30 PM
$24
8 - 12 min

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Directions

Firecakes Donuts
7:00 PM - 8:30 PM
$38
Day 3
+

$186

·

$ 5

Two Hearted Queen
7:30 AM - 8:30 AM
$14
10 - 15 min

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Directions

Wrigley Field
Ivy-clad walls & manual scoreboard add retro charm to the 2nd oldest baseball stadium in the majors.
9:00 AM - 12:00 PM
$100
6 - 9 min

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Directions

PR Italian Bistro
Award Winning, Italian-inspired Global Cuisine. Chef Owned. Named one of Chicago's Best Bistros -CBS Chicago
1:00 PM - 2:30 PM
$24
5 - 6 min

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Directions

The Chicago Diner, Lakeview
7:00 PM - 8:30 PM
$48
Day 4
+

$149

·

$ 5

Intelligentsia Coffee
7:30 AM - 8:30 AM
$24
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.
9:00 AM - 11:00 AM
Free
11 - 14 min

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Directions

Navy Pier
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
11:30 AM - 1:30 PM
$63
11 - 16 min

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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.
2:00 PM - 3:30 PM
$36
4 - 6 min

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Directions

Buona
Quick casual restaurant featuring Original Italian Beef, Pizza, Burgers, Hot Dogs, Sandwiches and Salads
7:00 PM - 8:30 PM
$26
Day 5
+

$208

Dmk
7:30 AM - 8:30 AM
$20
12 - 17 min

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Directions

Shedd Aquarium
State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.
9:00 AM - 12:00 PM
$100
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.
1:00 PM - 2:30 PM
$48
10 - 15 min

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Directions

Grant Park Bistro
7:00 PM - 8:30 PM
$40

Budget breakdown: $790 In total

Activities & Food:$775
Transport:$15