Exploring the Best of Chicago: 5-Day Itinerary

Jose Carlos Pupo Acosta

27 Oct 2023

Embark on an unforgettable journey through the vibrant city of Chicago with this 5-day itinerary. Discover 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

$63

$ 15

Hampton Inn Majestic Chicago Theatre District

Depart from your stay 🏨

8 - 11 min

Directions

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

8:00 AM - 10:00 AM

•

Free

10 - 12 min

Directions

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

No time set

•

$63

12 - 15 min

Directions

Pasta, steaks & seafood served in a sleek, group-friendly eatery backed by Giuliana & Bill Rancic.

No time set

•

Free

Day 2

$50

$ 10

Hampton Inn Majestic Chicago Theatre District

Depart from your stay 🏨

10 - 12 min

Directions

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

8:00 AM - 9:30 AM

•

Free

3 - 4 min

Directions

10:30 AM - 11:00 AM

•

$50

7 - 9 min

Directions

No time set

•

Free

8 - 12 min

Directions

Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.

No time set

•

Free

Day 3

$100

$ 10

Hampton Inn Majestic Chicago Theatre District

Depart from your stay 🏨

12 - 15 min

Directions

State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.

No time set

•

$100

Day 4

$63

$ 10

Hampton Inn Majestic Chicago Theatre District

Depart from your stay 🏨

10 - 12 min

Directions

Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.

No time set

•

$63

1 - 2 min

Directions

Fashionable bar & deck for craft cocktails & beers on the 94th floor with panoramic city views.

No time set

•

Free

Budget breakdown: $320 In total

Activities & Food:$275

Transport:$45