Discover the Best of Chicago: 4-Day Itinerary

Mateusz Chwietczuk

10 Oct 2023

Experience the vibrant city of Chicago with this exciting 4-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

$96

$ 3

Club Quarters Hotel Central Loop, Chicago

Depart from your stay 🏨

11 - 16 min

Directions

Club Quarters Hotel Central Loop, Chicago

Modern rooms & suites in a polished hotel with a 24-hour gym, loaner iPads & an English-style pub.

7:30 AM - 7:30 AM

•

Free

10 - 12 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

8 - 11 min

Directions

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

10:30 AM - 12:00 PM

•

$31

8 - 11 min

Directions

1:00 PM - 2:30 PM

•

$36

Urban American tavern in Chicago's Block 37

7:00 PM - 8:30 PM

•

$28

Modern rooms & suites in a polished hotel with a 24-hour gym, loaner iPads & an English-style pub.

7:30 AM - 7:30 AM

•

Free

Day 2

$113

$ 5

Club Quarters Hotel Central Loop, Chicago

Depart from your stay 🏨

6 - 8 min

Directions

Modern rooms & suites in a polished hotel with a 24-hour gym, loaner iPads & an English-style pub.

7:30 AM - 7:30 AM

•

Free

13 - 20 min

Directions

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

8:00 AM - 10:00 AM

•

Free

12 - 18 min

Directions

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

10:30 AM - 1:30 PM

•

$50

7 - 10 min

Directions

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

2:00 PM - 3:30 PM

•

$28

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.

7:00 PM - 8:30 PM

•

$35

Modern rooms & suites in a polished hotel with a 24-hour gym, loaner iPads & an English-style pub.

7:30 AM - 7:30 AM

•

Free

Day 3

$92

$ 3

Club Quarters Hotel Central Loop, Chicago

Depart from your stay 🏨

6 - 8 min

Directions

Modern rooms & suites in a polished hotel with a 24-hour gym, loaner iPads & an English-style pub.

7:30 AM - 7:30 AM

•

Free

9 - 14 min

Directions

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

8:00 AM - 9:00 AM

•

Free

4 - 5 min

Directions

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

9:30 AM - 12:30 PM

•

$31

2 - 3 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

•

$32

7:00 PM - 8:30 PM

•

$28

Modern rooms & suites in a polished hotel with a 24-hour gym, loaner iPads & an English-style pub.

7:30 AM - 7:30 AM

•

Free

Day 4

$88

$ 8

Club Quarters Hotel Central Loop, Chicago

Depart from your stay 🏨

11 - 14 min

Directions

Modern rooms & suites in a polished hotel with a 24-hour gym, loaner iPads & an English-style pub.

7:30 AM - 7:30 AM

•

Free

10 - 12 min

Directions

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

8:00 AM - 10:00 AM

•

$31

6 - 9 min

Directions

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

10:30 AM - 12:30 PM

•

Free

7 - 10 min

Directions

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

•

$29

7:00 PM - 8:30 PM

•

$27

Modern rooms & suites in a polished hotel with a 24-hour gym, loaner iPads & an English-style pub.

7:30 AM - 7:30 AM

•

Free

Budget breakdown: $405 In total

Activities & Food:$387

Transport:$18