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Discover the Vibrant Charms of Chicago: A 5-Day Itinerary

Manuel León Achon

1 Oct 2023

0

Embark on an unforgettable journey through the cultural wonders of Chicago. Explore iconic landmarks, world-class museums, and indulge in delectable cuisine. Get ready for an adventure of a lifetime!

Trip to Chicago

Tours & Activities

Viator Tours

Day 1

+

$139

·

$ 10

Museum of Contemporary Photography

Museum offering programs & events, with a U.S.-focused permanent collection & rotating exhibits.

8:00 AM - 9:00 AM

•

Free

12 - 17 min

~

Directions

Cloud Gate

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

9:30 AM - 10:30 AM

•

Free

7 - 9 min

~

Directions

Navy Pier

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

11:00 AM - 1:00 PM

•

$63

10 - 12 min

~

Directions

Chicago History Museum

Photos, artifacts, newsreels & dioramas bring to life historical events, architecture & culture.

1:30 PM - 3:30 PM

•

$50

11 - 16 min

~

Directions

North Avenue Beach

4:00 PM - 6:00 PM

•

Free

16 - 23 min

~

Directions

Chicago Pizza & Oven Grinder

7:00 PM - 8:30 PM

•

$26

Day 2

+

$176

·

$ 10

International Museum of Surgical Science

Paintings, sculptures & exhibits help tell the history of surgery from ancient times to the present.

8:00 AM - 9:30 AM

•

$38

5 - 6 min

~

Directions

Museum Of Contemporary Art Chicago

Downtown museum showcasing post-World War II paintings, sculptures, photos, videos & performances.

10:00 AM - 11:30 AM

•

$38

9 - 11 min

~

Directions

Millennium Park

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

12:00 PM - 2:00 PM

•

Free

5 - 8 min

~

Directions

The Art Institute of Chicago

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

2:30 PM - 5:30 PM

•

$63

6 - 9 min

~

Directions

Garrett Popcorn Shops

7:00 PM - 8:30 PM

•

$38

Day 3

+

$216

·

$ 10

Skydeck Chicago

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

8:00 AM - 9:30 AM

•

$63

5 - 6 min

~

Directions

The Chicago Theatre

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

10:00 AM - 12:00 PM

•

$75

4 - 5 min

~

Directions

American Writers Museum

Modern literary center with immersive displays on famed writers like Emily Dickinson & Jack Kerouac.

12:30 PM - 2:00 PM

•

$30

5 - 6 min

~

Directions

Buckingham Fountain

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

2:30 PM - 3:30 PM

•

Free

4 - 5 min

~

Directions

Grant Park

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

4:00 PM - 6:00 PM

•

Free

7 - 10 min

~

Directions

Grant Park Bistro

7:00 PM - 8:30 PM

•

$48

Day 4

+

$151

Chicago Symphony Orchestra

Built in 1904, music complex that hosts the Chicago Symphony Orchestra & classical & jazz concerts.

8:00 AM - 10:00 AM

•

$75

6 - 9 min

~

Directions

Museum of Illusions Chicago

Immersive rooms with optical illusions & holograms designed to deceive the eye, popular for photos.

10:30 AM - 12:00 PM

•

$50

4 - 6 min

~

Directions

The Picasso

Untitled 50-ft., 160-ton Cor-Ten steel sculpture by artist Pablo Picasso, dedicated in 1967.

12:30 PM - 1:30 PM

•

Free

12 - 17 min

~

Directions

Riverwalk

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

2:00 PM - 4:00 PM

•

Free

6 - 9 min

~

Directions

Roti Modern Mediterranean

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

7:00 PM - 8:30 PM

•

$26

Day 5

+

$190

·

$ 25

The 606

Created on a former rail line, this elevated, 2.7 mile landscaped trail draws runners & bikers.

8:00 AM - 9:30 AM

•

Free

22 - 27 min

~

Directions

National Museum of Mexican Art

Some 18,000 paintings, photographs, sculptures & more are housed at this art museum.

10:00 AM - 11:30 AM

•

Free

12 - 15 min

~

Directions

WNDR Museum

Multi-sensory, contemporary installations by artists including Yayoi Kusama.

12:00 PM - 1:30 PM

•

$63

8 - 12 min

~

Directions

Kavi Gupta Gallery | Washington Blvd

Gallery displaying contemporary art by emerging artists across all media, from paintings to film.

2:00 PM - 3:00 PM

•

Free

14 - 17 min

~

Directions

Adler Planetarium

Interactive exhibits & high-tech sky shows entertain stargazers, lakefront views are a bonus.

3:30 PM - 6:30 PM

•

$88

16 - 20 min

~

Directions

Plein Air Cafe & Eatery

7:00 PM - 8:30 PM

•

$40

7 - 9 min

~

Directions

Stony Island Arts Bank

8:30 PM - 9:30 PM

•

Free

Budget breakdown: $926 In total

Activities & Food:$871

Transport:$55