Discover the Vibrant Charm of Chicago: 9-Day Itinerary

Valeria Castañeda Toledo

17 Oct 2023

Embark on a thrilling 9-day journey through the captivating city of Chicago. Immerse yourself in the rich culture, iconic landmarks, and delectable cuisine that make this city truly unique. From stunning beaches to world-class museums, this itinerary has it all!

Trip to Chicago

Tours & Activities

Viator Tours

Day 1

$248

$ 80

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

8:00 AM - 9:00 AM

•

Free

12 - 15 min

Directions

Small, free zoo with lions, primates, reptiles, a children's area & an interactive farm exhibit.

9:30 AM - 11:30 AM

•

Free

5 - 8 min

Directions

Thousands of exotic plants in an 1890 glass structure, plus outdoor gardens & fountains.

12:00 PM - 1:00 PM

•

Free

19 - 23 min

Directions

1:30 PM - 3:00 PM

•

$144

7 - 9 min

Directions

Seasonal sand beach offering an enclosed dog area, water sports & a festive bar/restaurant.

3:00 PM - 5:00 PM

•

Free

8 - 10 min

Directions

7:00 PM - 8:30 PM

•

$104

Day 2

$248

$ 20

Sandy, north-facing public beach on Lake Michigan, popular for open-water swimming & skyline views.

8:00 AM - 10:00 AM

•

Free

12 - 15 min

Directions

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

10:30 AM - 12:30 PM

•

Free

14 - 21 min

Directions

1:00 PM - 2:30 PM

•

$96

4 - 5 min

Directions

Thousands of historic radio & TV programs plus commercials comprise this 4-floor museum.

2:30 PM - 4:00 PM

•

Free

8 - 12 min

Directions

An 1800s Catholic church with a vaulted ceiling & colorful stained glass, offering guided tours.

4:30 PM - 5:30 PM

•

Free

4 - 5 min

Directions

Step into Italy, and experience authentic food and wine full of fun and excitement!

7:00 PM - 8:30 PM

•

$152

Day 3

$288

$ 40

Prairie-style garden with trails, filled with native plants & home to birds, frogs & other wildlife.

8:00 AM - 9:00 AM

•

Free

13 - 16 min

Directions

Neo-Gothic skyscraper influenced by Rouen Cathedral & decorated with rocks from world landmarks.

9:30 AM - 10:30 AM

•

Free

8 - 11 min

Directions

Free art & shows in an 1897 Beaux-Arts building with vaulted lobby, mosaics & 2 stained-glass domes.

11:00 AM - 12:00 PM

•

Free

6 - 8 min

Directions

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

12:30 PM - 1:30 PM

•

Free

4 - 6 min

Directions

2:00 PM - 3:30 PM

•

$96

7 - 10 min

Directions

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

3:30 PM - 5:30 PM

•

Free

8 - 11 min

Directions

7:00 PM - 8:30 PM

•

$192

Day 4

$248

$ 40

Baha'i temple, one of 8 in the world, featuring a 135-ft white-stone dome completed in 1953.

8:00 AM - 9:30 AM

•

Free

45 - 54 min

Directions

10:00 AM - 11:00 AM

•

Free

7 - 10 min

Directions

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

11:30 AM - 12:30 PM

•

Free

9 - 11 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.

1:00 PM - 2:30 PM

•

$144

12 - 18 min

Directions

57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.

2:30 PM - 5:30 PM

•

Free

11 - 16 min

Directions

7:00 PM - 8:30 PM

•

$104

Day 5

$578

$ 20

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

8:00 AM - 9:30 AM

•

$250

8 - 10 min

Directions

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

10:00 AM - 11:00 AM

•

Free

3 - 4 min

Directions

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

11:30 AM - 1:30 PM

•

Free

8 - 11 min

Directions

2:00 PM - 3:30 PM

•

$192

6 - 9 min

Directions

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

3:30 PM - 4:30 PM

•

Free

11 - 16 min

Directions

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

5:00 PM - 6:00 PM

•

Free

12 - 17 min

Directions

7:00 PM - 8:30 PM

•

$136

Day 6

$352

$ 40

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

8:00 AM - 9:30 AM

•

Free

7 - 9 min

Directions

Suburban recreational area with soccer & baseball fields, tennis courts & playgrounds, plus a beach.

10:00 AM - 12:00 PM

•

Free

12 - 18 min

Directions

12:30 PM - 2:00 PM

•

$160

11 - 16 min

Directions

National Museum of Puerto Rican Arts & Culture

2:00 PM - 3:30 PM

•

Free

20 - 24 min

Directions

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

4:00 PM - 5:30 PM

•

Free

5 - 8 min

Directions

A Foodie Favorite. We've been serving up the Best Authentic Carnitas in Chicago since 1975!

7:00 PM - 8:30 PM

•

$192

Day 7

$272

$ 20

Garfield Park Conservatory - Reservations Required

184-acre park with a swimming pool, fishing lagoon, athletic fields & tennis courts.

8:00 AM - 9:30 AM

•

Free

20 - 24 min

Directions

North America's 2nd-largest opera venue has over 3,500 seats & houses the Lyric Opera of Chicago.

10:00 AM - 11:30 AM

•

Free

10 - 15 min

Directions

Huge building featuring high-end home design & furniture showrooms, plus a lineup of trade shows.

12:00 PM - 1:00 PM

•

Free

12 - 18 min

Directions

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

1:30 PM - 3:00 PM

•

$136

7 - 10 min

Directions

Daley Center's open-air courtyard with a huge Picasso sculpture, benches & seasonal farmer's market.

3:00 PM - 4:00 PM

•

Free

2 - 3 min

Directions

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

4:30 PM - 5:30 PM

•

Free

3 - 4 min

Directions

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

•

$136

Day 8

$620

$ 60