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Discover the Best of Chicago: 8-Day Itinerary

oscar andres rodriguez ortiz

oscar andres rodriguez ortiz

19 Nov 2023

Embark on an unforgettable journey through the vibrant city of Chicago with this 8-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
+

$141

·

$ 10

Kanela Breakfast Club
7:30 AM - 8:30 AM
•
$16
9 - 14 min

~

Directions

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

~

Directions

360 CHICAGO
Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.
11:30 AM - 1:00 PM
•
$63
10 - 12 min

~

Directions

Wildberry Pancakes & Cafe
1:30 PM - 3:00 PM
•
$36
5 - 8 min

~

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

~

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
+

$180

Just Salad
7:30 AM - 8:30 AM
•
$30
4 - 6 min

~

Directions

The Art Institute of Chicago
Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
9:00 AM - 12:00 PM
•
$64
9 - 14 min

~

Directions

Buckingham Fountain
Among the world’s largest, Grant Park’s 3-level rococo fountain (1927) offers light & water shows.
12:30 PM - 1:30 PM
•
Free
10 - 15 min

~

Directions

Grant Park Bistro
7:00 PM - 8:30 PM
•
$48
11 - 16 min

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Directions

Garrett Popcorn Shops
7:00 PM - 8:30 PM
•
$38
Day 3
+

$86

Intelligentsia Coffee
7:30 AM - 8:30 AM
•
$14
5 - 8 min

~

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
12 - 17 min

~

Directions

Grant Park
312-acre centerpiece of Downtown housing some of the city's busiest attractions.
11:30 AM - 1:30 PM
•
Free
8 - 11 min

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Directions

Cafecito
2:00 PM - 3:30 PM
•
$24
7 - 10 min

~

Directions

Grant Park Bistro
7:00 PM - 8:30 PM
•
$48
Day 4
+

$350

·

$ 10

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
•
$24
8 - 12 min

~

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
16 - 20 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.
11:30 AM - 2:30 PM
•
$264
6 - 9 min

~

Directions

PR Italian Bistro
Award Winning, Italian-inspired Global Cuisine. Chef Owned. Named one of Chicago's Best Bistros -CBS Chicago
3:00 PM - 4:30 PM
•
$36
6 - 8 min

~

Directions

Two Hearted Queen
7:00 PM - 8:30 PM
•
$26
Day 5
+

$165

·

$ 5

Lou Mitchell's Restaurant & Bakery
Lou Mitchell’s is not only a classic Chicago icon, but our food is recognized both nationally and internationally with endless accolades. Among the list are USA Today, American Way, newspapers, magazines, food critics, television. It’s a must see place.
7:30 AM - 8:30 AM
•
$20
7 - 10 min

~

Directions

Willis Tower
Iconic, 110-story skyscraper featuring expansive views of Chicago from its 103rd-story Skydeck.
9:00 AM - 11:00 AM
•
$63
9 - 11 min

~

Directions

Museum Campus
57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.
11:30 AM - 2:30 PM
•
Free
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.
3:00 PM - 4:30 PM
•
$48
8 - 11 min

~

Directions

Eleven City Diner
2:30 PM - 4:00 PM
•
$34
Day 6
+

$185

·

$ 10

B'Gabs
Raw, vegan, gluten-free, soy-free, peanut-free, smoothie bar, juice bar, herbs, tea, essential oils
7:30 AM - 8:30 AM
•
$22
8 - 11 min

~

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
•
$75
5 - 6 min

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Directions

Plein Air Cafe & Eatery
1:30 PM - 3:00 PM
•
$40
6 - 8 min

~

Directions

Virtue Restaurant
7:00 PM - 8:30 PM
•
$48
Day 7
+

$249

·

$ 10

Intelligentsia Coffee
7:30 AM - 8:30 AM
•
$18
7 - 10 min

~

Directions

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
9:00 AM - 10:30 AM
•
$63
14 - 17 min

~

Directions

Shedd Aquarium
State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.
11:00 AM - 2:00 PM
•
$100
8 - 10 min

~

Directions

Eleven City Diner
2:30 PM - 4:00 PM
•
$34
4 - 6 min

~

Directions

Flo & Santos
Polish/Italian. Pizza/pierogi Craft beer/polish vodkas
7:00 PM - 8:30 PM
•
$34
Day 8
+

$173

·

$ 5

Dmk
7:30 AM - 8:30 AM
•
$30
11 - 16 min

~

Directions

Field Museum
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
9:00 AM - 12:00 PM
•
$63
9 - 11 min

~

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
12:30 PM - 2:00 PM
•
$36
5 - 8 min

~

Directions

Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
2:00 PM - 4:00 PM
•
Free
5 - 8 min

~

Directions

The Purple Pig
7:00 PM - 8:30 PM
•
$44

Budget breakdown: $1577 In total

Activities & Food:$1527
Transport:$50