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Discover the Best of Chicago: 8-Day Itinerary

Rodrigo Contreras

Rodrigo Contreras

17 Nov 2023

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

Trip to Chicago

Day 1
+

$187

·

$ 10

Willis Tower
Iconic, 110-story skyscraper featuring expansive views of Chicago from its 103rd-story Skydeck.
8:00 AM - 10:00 AM
•
$63
14 - 17 min

~

Directions

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

~

Directions

Chicago Pizza & Oven Grinder
12:30 PM - 2:00 PM
•
$36
6 - 9 min

~

Directions

Lincoln Park Zoo
Small, free zoo with lions, primates, reptiles, a children's area & an interactive farm exhibit.
2:00 PM - 4:00 PM
•
Free
11 - 16 min

~

Directions

Firecakes Donuts
7:00 PM - 8:30 PM
•
$26
Day 2
+

$147

·

$ 10

Navy Pier
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
8:00 AM - 10:00 AM
•
Free
5 - 8 min

~

Directions

Chicago Children's Museum
Family museum on Navy Pier with lots of interactive exhibits, including many for young kids.
10:30 AM - 12:30 PM
•
$38
10 - 12 min

~

Directions

Cafecito
1:00 PM - 2:30 PM
•
$24
4 - 5 min

~

Directions

Museum Of Contemporary Art Chicago
Downtown museum showcasing post-World War II paintings, sculptures, photos, videos & performances.
2:30 PM - 4:00 PM
•
$38
8 - 10 min

~

Directions

Cloud Gate
Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.
4:30 PM - 5:30 PM
•
Free
5 - 8 min

~

Directions

Wildberry Pancakes & Cafe
7:00 PM - 8:30 PM
•
$48
Day 3
+

$336

·

$ 10

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
•
$264
14 - 17 min

~

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
5 - 6 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.
1:00 PM - 2:30 PM
•
$24
12 - 18 min

~

Directions

Museum Campus
57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.
2:30 PM - 5:30 PM
•
Free
11 - 16 min

~

Directions

Eleven City Diner
7:00 PM - 8:30 PM
•
$48
Day 4
+

$184

·

$ 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
•
$100
8 - 10 min

~

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
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.
2:00 PM - 3:30 PM
•
$36
4 - 5 min

~

Directions

Chicago Cultural Center
Free art & shows in an 1897 Beaux-Arts building with vaulted lobby, mosaics & 2 stained-glass domes.
3:30 PM - 4:30 PM
•
Free
4 - 5 min

~

Directions

Wildberry Pancakes & Cafe
7:00 PM - 8:30 PM
•
$48
Day 5
+

$151

·

$ 5

Field Museum
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
8:00 AM - 11:00 AM
•
$63
7 - 9 min

~

Directions

Crown Fountain
Public sculpture with 2 50-ft. LED towers & a reflecting pool, by Catalan artist Jaume Plensa.
11:30 AM - 12:30 PM
•
Free
7 - 10 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
1:00 PM - 2:30 PM
•
$48
5 - 8 min

~

Directions

Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
2:30 PM - 4:30 PM
•
Free
5 - 8 min

~

Directions

The Purple Pig
7:00 PM - 8:30 PM
•
$40
Day 6
+

$227

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

~

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
•
$64
8 - 11 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.
2:00 PM - 3:30 PM
•
$40
6 - 9 min

~

Directions

The Chicago Theatre
French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.
3:30 PM - 5:30 PM
•
$75
6 - 9 min

~

Directions

Wildberry Pancakes & Cafe
7:00 PM - 8:30 PM
•
$48
Day 7
+

$118

·

$ 15

Brookfield Zoo
Lions, tigers, dolphins & more frolic in natural indoor & outdoor settings at this wildlife park.
8:00 AM - 12:00 PM
•
$50
33 - 40 min

~

Directions

Rootstock Wine & Beer Bar
12:30 PM - 2:00 PM
•
$34
6 - 8 min

~

Directions

Garfield Park Conservatory - Reservations Required
184-acre park with a swimming pool, fishing lagoon, athletic fields & tennis courts.
2:00 PM - 3:30 PM
•
Free
8 - 10 min

~

Directions

Flying Saucer
7:00 PM - 8:30 PM
•
$34
Day 8
+

$155

·

$ 15

Museum of Science and Industry, Chicago
Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.
8:00 AM - 12:00 PM
•
$75
5 - 6 min

~

Directions

Plein Air Cafe & Eatery
12:30 PM - 2:00 PM
•
$36
6 - 8 min

~

Directions

Jackson (Andrew) Park
540-plus-acre city park featuring a beach, gardens & indoor/outdoor fitness facilities.
2:00 PM - 4:00 PM
•
Free
8 - 10 min

~

Directions

The Promontory
7:00 PM - 8:30 PM
•
$44

Budget breakdown: $1575 In total

Activities & Food:$1505
Transport:$70