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10 Days in the Windy City

Danillo de Oliveira

Danillo de Oliveira

7 Dec 2023

Embark on an unforgettable journey through the vibrant streets of Chicago. Discover iconic landmarks, savor mouthwatering cuisine, and immerse yourself in the city's rich culture. Get ready for an adventure of a lifetime!

Day 1Sports, Art, and Fine Dining
+

$194

·

$ 3

Wrigley Field
Ivy-clad walls & manual scoreboard add retro charm to the 2nd oldest baseball stadium in the majors.
8:00 AM - 11:00 AM
$132
16 - 20 min

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Directions

Cloud Gate
Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.
11:30 AM - 12:30 PM
Free
4 - 6 min

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Directions

Cherry Circle Room
1:00 PM - 2:30 PM
$36
2 - 3 min

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Directions

The Gage
We invite you to savor our delicious, upscale comfort food, fine wines, boutique beers and whiskeys while enjoying the relaxing ambience of our vintage decor.
1:00 PM - 2:30 PM
$26
Day 2Nature's Beauty and Sky-High Thrills
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$126

·

$ 5

Garfield Park Conservatory - Reservations Required
184-acre park with a swimming pool, fishing lagoon, athletic fields & tennis courts.
8:00 AM - 9:30 AM
Free
11 - 14 min

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Directions

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
10:00 AM - 11:30 AM
$31
13 - 16 min

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Directions

360 CHICAGO
Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.
12:00 PM - 1:30 PM
$31
4 - 5 min

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Directions

Cafecito
2:00 PM - 3:30 PM
$28
8 - 11 min

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Directions

Le Colonial Chicago
7:00 PM - 8:30 PM
$35
Day 3Wildlife, Waterfront, and Culinary Delights
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$60

·

$ 3

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
14 - 17 min

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Directions

Navy Pier
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
10:30 AM - 12:30 PM
Free
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.
1:00 PM - 2:30 PM
$32
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
$28
Day 4Museums, Riverwalk, and Gastronomic Delights
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$75

·

$ 3

Chicago Children's Museum
Family museum on Navy Pier with lots of interactive exhibits, including many for young kids.
8:00 AM - 10:00 AM
$19
13 - 16 min

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Directions

Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
10:30 AM - 12:30 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
1:00 PM - 2:30 PM
$29
7 - 10 min

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Directions

The Purple Pig
7:00 PM - 8:30 PM
$27
Day 5Culture, Parks, and Pancake Paradise
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$55

·

$ 3

Museum Campus
57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.
8:00 AM - 11:00 AM
Free
5 - 6 min

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Directions

Millennium Park
24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.
11:30 AM - 1:30 PM
Free
5 - 8 min

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Directions

Wildberry Pancakes & Cafe
2:00 PM - 3:30 PM
$29
6 - 9 min

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Directions

The Gage
We invite you to savor our delicious, upscale comfort food, fine wines, boutique beers and whiskeys while enjoying the relaxing ambience of our vintage decor.
1:00 PM - 2:30 PM
$26
Day 6Aquatic Wonders and Iconic Landmarks
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$103

·

$ 5

Shedd Aquarium
State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.
8:00 AM - 11:00 AM
$50
5 - 6 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.
11:30 AM - 12:30 PM
Free
12 - 17 min

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Directions

The Gage
We invite you to savor our delicious, upscale comfort food, fine wines, boutique beers and whiskeys while enjoying the relaxing ambience of our vintage decor.
1:00 PM - 2:30 PM
$26
7 - 9 min

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Directions

Lou Malnati's Pizzeria
Full-service restaurant.
7:00 PM - 8:30 PM
$27
Day 7History, Brunch, and Craft Beer
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$97

Field Museum
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
8:00 AM - 11:00 AM
$31
9 - 14 min

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Directions

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
1:00 PM - 2:30 PM
$29
7 - 10 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
$36
Day 8Parks, Art, and Popcorn Pleasures
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$103

Grant Park
312-acre centerpiece of Downtown housing some of the city's busiest attractions.
8:00 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
$36
12 - 18 min

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Directions

Giordano's
Famous Chicago-style deep dish pizza right in your neighborhood. Visit us for a family-friendly atmosphere and delicious food or order your meal online for pickup or delivery.
7:00 PM - 8:30 PM
$35
Day 9Science, Music, and Culinary Bliss
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$100

·

$ 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
$38
5 - 6 min

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Directions

The Promontory
1:00 PM - 2:30 PM
$31
6 - 8 min

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Directions

Plein Air Cafe & Eatery
7:00 PM - 8:30 PM
$31
Day 10Parks, Skyline Views, Theater, and Pizza Heaven
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$137

·

$ 3

Jackson (Andrew) Park
540-plus-acre city park featuring a beach, gardens & indoor/outdoor fitness facilities.
8:00 AM - 10:00 AM
Free
16 - 20 min

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Directions

Willis Tower
Iconic, 110-story skyscraper featuring expansive views of Chicago from its 103rd-story Skydeck.
10:30 AM - 12:30 PM
$31
12 - 17 min

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Directions

The Dearborn
Urban American tavern in Chicago's Block 37
1:00 PM - 2:30 PM
$33
4 - 5 min

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Directions

The Chicago Theatre
French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.
2:30 PM - 4:30 PM
$38
4 - 6 min

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Directions

Giordano's
Famous Chicago-style deep dish pizza right in your neighborhood. Visit us for a family-friendly atmosphere and delicious food or order your meal online for pickup or delivery.
7:00 PM - 8:30 PM
$35

Budget breakdown: $1076 In total

Activities & Food:$1048
Transport:$28