Discover the Best of Chicago: 4-Day Itinerary

Eduardo Aparicio

14 Oct 2023

Embark on an unforgettable journey through the vibrant city of Chicago. Experience 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

$686

$ 15

Chicago Marriott Downtown Magnificent Mile

Depart from your stay 🏨

12 - 17 min

Directions

Chicago Marriott Downtown Magnificent Mile

Polished high-rise property offering farm-to-table dining, meeting space & a rooftop garden.

7:30 AM - 7:30 AM

•

Free

7 - 10 min

Directions

7:30 AM - 8:30 AM

•

$114

10 - 12 min

Directions

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

9:00 AM - 10:30 AM

•

$188

3 - 4 min

Directions

Beloved 1924 addition to the city skyline, whose clock tower stands 425 ft above street level.

11:00 AM - 12:00 PM

•

Free

3 - 4 min

Directions

1:00 PM - 2:30 PM

•

$216

Shaw’s is two restaurants in one – a jazzy, sophisticated, seafood restaurant and a carefree, lively oyster bar. Both serve top-grade fish and shellfish, several varieties of just-shucked oysters, and inventive sushi and sashimi combinations, made with the freshest fish in town.

7:00 PM - 8:30 PM

•

$168

Polished high-rise property offering farm-to-table dining, meeting space & a rooftop garden.

7:30 AM - 7:30 AM

•

Free

Day 2

$498

$ 15

Chicago Marriott Downtown Magnificent Mile

Depart from your stay 🏨

8 - 12 min

Directions

Polished high-rise property offering farm-to-table dining, meeting space & a rooftop garden.

7:30 AM - 7:30 AM

•

Free

6 - 9 min

Directions

Fisk & Co blends the vibe of Belgium’s lively bistros with the spirit of Chicago’s historic restaurant industry.

7:30 AM - 8:30 AM

•

$138

10 - 15 min

Directions

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

9:00 AM - 11:00 AM

•

Free

4 - 6 min

Directions

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

11:30 AM - 12:30 PM

•

Free

2 - 3 min

Directions

1:00 PM - 2:30 PM

•

$168

We invite you to savor our delicious, upscale comfort food, fine wines, boutique beers and whiskeys while enjoying the relaxing ambience of our vintage decor.

1:00 PM - 2:30 PM

•

$192

Polished high-rise property offering farm-to-table dining, meeting space & a rooftop garden.

7:30 AM - 7:30 AM

•

Free

Day 3

$486

$ 30

Chicago Marriott Downtown Magnificent Mile

Depart from your stay 🏨

11 - 16 min

Directions

Polished high-rise property offering farm-to-table dining, meeting space & a rooftop garden.

7:30 AM - 7:30 AM

•

Free

5 - 8 min

Directions

7:30 AM - 8:30 AM

•

$126

11 - 16 min

Directions

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

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

We invite you to savor our delicious, upscale comfort food, fine wines, boutique beers and whiskeys while enjoying the relaxing ambience of our vintage decor.

1:00 PM - 2:30 PM

•

$192

Full-service restaurant.

7:00 PM - 8:30 PM

•

$168

Polished high-rise property offering farm-to-table dining, meeting space & a rooftop garden.

7:30 AM - 7:30 AM

•

Free

Day 4

$656

$ 45

Chicago Marriott Downtown Magnificent Mile

Depart from your stay 🏨

17 - 21 min

Directions

Polished high-rise property offering farm-to-table dining, meeting space & a rooftop garden.

7:30 AM - 7:30 AM

•

Free

5 - 8 min

Directions

Blends the bold flavors + savory spices found in Puerto Rico, South East Asia, China, Japan and Korea. Comfort foods from the motherland with a twist.

7:30 AM - 8:30 AM

•

$132

12 - 15 min

Directions