Discover the Vibrant Charm of Chicago: An 8-Day Itinerary

Claudia Cano

12 Oct 2023

Embark on an unforgettable journey through the Windy City with this 8-day itinerary to Chicago. Explore iconic landmarks like Buckingham Fountain, Cloud Gate, and The Art Institute of Chicago. Immerse yourself in the city's rich culture, visit world-class museums, and soak in the breathtaking views from Skydeck Chicago. Get ready for an adventure of a lifetime!

Trip to Chicago

Tours & Activities

Viator Tours

Day 1

$ 10

Trump International Hotel & Tower® Chicago

Depart from your stay 🏨

18 - 22 min

Directions

Trump International Hotel & Tower® Chicago

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

9 - 11 min

Directions

Lake island & park, home to Huntington Bank Pavilion amphitheater, nature trails & skyline vistas.

8:00 AM - 10:00 AM

•

Free

11 - 16 min

Directions

Among the world’s largest, Grant Park’s 3-level rococo fountain (1927) offers light & water shows.

10:30 AM - 11:30 AM

•

Free

Public sculpture with 2 50-ft. LED towers & a reflecting pool, by Catalan artist Jaume Plensa.

12:00 PM - 1:00 PM

•

Free

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

Day 2

$75

$ 10

Trump International Hotel & Tower® Chicago

Depart from your stay 🏨

21 - 26 min

Directions

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.

8:00 AM - 12:00 PM

•

$75

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

Day 3

$100

$ 10

Trump International Hotel & Tower® Chicago

Depart from your stay 🏨

18 - 22 min

Directions

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

8 - 10 min

Directions

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

8:00 AM - 11:00 AM

•

$100

Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.

11:30 AM - 12:30 PM

•

Free

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

Day 4

$63

$ 15

Trump International Hotel & Tower® Chicago

Depart from your stay 🏨

15 - 18 min

Directions

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

10 - 12 min

Directions

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

8:00 AM - 11:00 AM

•

$63

Art deco skyscraper, once Chicago's tallest, topped with a statue of Roman goddess Ceres.

11:30 AM - 12:30 PM

•

Free

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

Day 5

$63

$ 10

Trump International Hotel & Tower® Chicago

Depart from your stay 🏨

13 - 16 min

Directions

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

10 - 12 min

Directions

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

8:00 AM - 9:30 AM

•

$63

3 - 4 min

Directions

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

10:00 AM - 12:00 PM

•

Free

Long-standing drawbridge honoring a founder of Chicago & decorated with sculptures & plaques.

12:30 PM - 1:30 PM

•

Free

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

Day 6

$75

Trump International Hotel & Tower® Chicago

Depart from your stay 🏨

7 - 10 min

Directions

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

8 - 11 min

Directions

French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.

8:00 AM - 10:00 AM

•

$75

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

10:30 AM - 12:30 PM

•

Free

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

Day 7

$63

$ 10

Trump International Hotel & Tower® Chicago

Depart from your stay 🏨

11 - 14 min

Directions

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

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

8:00 AM - 11:00 AM

•

$63

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

Day 8

$125

$ 15

Trump International Hotel & Tower® Chicago

Depart from your stay 🏨

8 - 10 min

Directions

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

10 - 12 min

Directions

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

8:00 AM - 9:30 AM

•

$63

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

10:00 AM - 12:00 PM

•

$63

Sleek quarters offering skyline and lake views, plus a renowned restaurant, a rooftop terrace & spa.

7:30 AM - 7:30 AM

•

Free

Budget breakdown: $643 In total

Activities & Food:$563

Transport:$80