Chicago Adventure: 5-Day Itinerary

Joaquin Casillas

8 Oct 2023

Embark on an exciting 5-day journey through the vibrant city of Chicago. 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

$239

$ 15

Jaslin Hotel

Depart from your stay 🏨

15 - 18 min

Directions

Polished rooms & suites in a low-key hotel with city views & a fitness center, plus a lobby lounge.

7:30 AM - 7:30 AM

•

Free

9 - 14 min

Directions

7:30 AM - 8:30 AM

•

$16

14 - 17 min

Directions

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

9:00 AM - 11:00 AM

•

$63

16 - 23 min

Directions

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

11:30 AM - 2:30 PM

•

$100

10 - 15 min

Directions

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

12:30 PM - 2:00 PM

•

$24

Polished rooms & suites in a low-key hotel with city views & a fitness center, plus a lobby lounge.

7:30 AM - 7:30 AM

•

Free

Day 2

$203

$ 15

Jaslin Hotel

Depart from your stay 🏨

8 - 10 min

Directions

Polished rooms & suites in a low-key hotel with city views & a fitness center, plus a lobby lounge.

7:30 AM - 7:30 AM

•

Free

7 - 10 min

Directions

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

•

$30

4 - 5 min

Directions

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

9:00 AM - 10:30 AM

•

$63

8 - 11 min

Directions

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

11:00 AM - 12:00 PM

•

Free

6 - 9 min

Directions

12:30 PM - 2:00 PM

•

$24

9 - 14 min

Directions

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

2:00 PM - 5:00 PM

•

$63

10 - 15 min

Directions

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

5:30 PM - 6:30 PM

•

Free

12:30 PM - 2:00 PM

•

$24

Polished rooms & suites in a low-key hotel with city views & a fitness center, plus a lobby lounge.

7:30 AM - 7:30 AM

•

Free

Day 3

$149

$ 15

Jaslin Hotel

Depart from your stay 🏨

8 - 10 min

Directions

Polished rooms & suites in a low-key hotel with city views & a fitness center, plus a lobby lounge.

7:30 AM - 7:30 AM

•

Free

10 - 15 min

Directions

7:30 AM - 8:30 AM

•

$14

12 - 17 min

Directions

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

9:00 AM - 12:00 PM

•

$63

7 - 10 min

Directions

12:30 PM - 2:00 PM

•

$24

6 - 8 min

Directions

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

2:00 PM - 4:00 PM

•

Free

3 - 4 min

Directions

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

4:30 PM - 5:30 PM

•

Free

7:00 PM - 8:30 PM

•

$48

Polished rooms & suites in a low-key hotel with city views & a fitness center, plus a lobby lounge.

7:30 AM - 7:30 AM

•

Free

Day 4

$161

$ 10

Jaslin Hotel

Depart from your stay 🏨

14 - 17 min

Directions

Polished rooms & suites in a low-key hotel with city views & a fitness center, plus a lobby lounge.

7:30 AM - 7:30 AM

•

Free

5 - 8 min

Directions

7:30 AM - 8:30 AM

•

$24

10 - 15 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

6 - 9 min

Directions

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

11:30 AM - 1:30 PM

•

Free

4 - 5 min

Directions

By Millenium Park at Lake and Michigan, Downtown Chicago restaurant Roti Modern Mediterranean offers a menu of deliciously fresh salads, bowls, & pitas

2:00 PM - 3:30 PM

•

$36

4 - 6 min

Directions

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

3:30 PM - 5:30 PM

•

$75

Fresh salads, plates + grain bowls available for pickup and delivery every day, made in-house from scratch, using whole produce delivered that morning.

7:00 PM - 8:30 PM

•

$26

Polished rooms & suites in a low-key hotel with city views & a fitness center, plus a lobby lounge.

7:30 AM - 7:30 AM

•

Free

Day 5

$208

$ 15

Jaslin Hotel

Depart from your stay 🏨