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Discover the Best of Chicago: 5-Day Itinerary

Luis Chaufon

16 Nov 2023

0

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

Tours & Activities

Viator Tours

Day 1

+

$227

·

$ 8

B'Gabs

Raw, vegan, gluten-free, soy-free, peanut-free, smoothie bar, juice bar, herbs, tea, essential oils

7:30 AM - 8:30 AM

•

$24

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

•

$113

18 - 22 min

~

Directions

Wildberry Pancakes & Cafe

1:30 PM - 3:00 PM

•

$54

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.

12:30 PM - 2:00 PM

•

$36

Day 2

+

$247

·

$ 15

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

•

$45

10 - 15 min

~

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

7 - 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.

12:30 PM - 2:00 PM

•

$36

6 - 9 min

~

Directions

Millennium Park

24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.

2:00 PM - 4:00 PM

•

Free

7 - 9 min

~

Directions

Skydeck Chicago

103rd floor of the Willis Tower with clear observation boxes & views extending to four states.

4:30 PM - 6:00 PM

•

$94

8 - 11 min

~

Directions

Garrett Popcorn Shops

12:30 PM - 2:00 PM

•

$72

Day 3

+

$317

·

$ 8

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

•

$21

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

•

$94

11 - 14 min

~

Directions

Field Museum

State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.

11:30 AM - 2:30 PM

•

$94

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

•

$36

4 - 6 min

~

Directions

Flo & Santos

Polish/Italian. Pizza/pierogi Craft beer/polish vodkas

7:00 PM - 8:30 PM

•

$72

Day 4

+

$279

·

$ 8

Dmk

7:30 AM - 8:30 AM

•

$36

10 - 15 min

~

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

•

$150

14 - 21 min

~

Directions

Grant Park Bistro

12:30 PM - 2:00 PM

•

$54

7 - 10 min

~

Directions

Grant Park

312-acre centerpiece of Downtown housing some of the city's busiest attractions.

2:00 PM - 4:00 PM

•

Free

8 - 10 min

~

Directions

Navy Pier

Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.

4:30 PM - 6:30 PM

•

Free

11 - 16 min

~

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.

7:00 PM - 8:30 PM

•

$39

Day 5

+

$654

·

$ 8

Two Hearted Queen

7:30 AM - 8:30 AM

•

$30

10 - 15 min

~

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

•

$396

20 - 24 min

~

Directions

Garrett Popcorn Shops

12:30 PM - 2:00 PM

•

$72

6 - 9 min

~

Directions

The Art Institute of Chicago

Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.

2:00 PM - 5:00 PM

•

$96

7 - 10 min

~

Directions

Cafecito

7:00 PM - 8:30 PM

•

$60

Budget breakdown: $1768 In total

Activities & Food:$1723

Transport:$45