Background
Trip Planner Logo

8 Days in the Windy City!

David Rodriguez

David Rodriguez

22 Dec 2023

Join me on an unforgettable journey through the vibrant streets of Chicago. From iconic landmarks to hidden gems, this blog will take you on a whirlwind adventure filled with art, culture, and mouthwatering cuisine.

Day 1Theatrical Delights and Glittering Bean
+

$75

·

$ 5

Chicago Marriott Downtown Magnificent Mile

Depart from your stay 🏨

11 - 16 min

~

Directions

The Chicago Theatre
French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.
8:00 AM - 10:00 AM
$75
5 - 8 min

~

Directions

Chicago Cultural Center
Free art & shows in an 1897 Beaux-Arts building with vaulted lobby, mosaics & 2 stained-glass domes.
10:30 AM - 11:30 AM
Free
4 - 5 min

~

Directions

Cloud Gate
Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.
12:00 PM - 1:00 PM
Free
Day 2Sky-high Views and Wild Encounters
+

$63

·

$ 15

Chicago Marriott Downtown Magnificent Mile

Depart from your stay 🏨

4 - 6 min

~

Directions

The Wrigley Building
Beloved 1924 addition to the city skyline, whose clock tower stands 425 ft above street level.
8:00 AM - 9:00 AM
Free
9 - 11 min

~

Directions

360 CHICAGO
Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.
9:30 AM - 11:00 AM
$63
11 - 14 min

~

Directions

Lincoln Park Zoo
Small, free zoo with lions, primates, reptiles, a children's area & an interactive farm exhibit.
11:30 AM - 1:30 PM
Free
5 - 8 min

~

Directions

Lincoln Park Conservatory
Thousands of exotic plants in an 1890 glass structure, plus outdoor gardens & fountains.
2:00 PM - 3:00 PM
Free
Day 3Pier Pleasures and Baseball Fever
+

$264

·

$ 15

Chicago Marriott Downtown Magnificent Mile

Depart from your stay 🏨

9 - 11 min

~

Directions

Navy Pier
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
8:00 AM - 10:00 AM
Free
16 - 20 min

~

Directions

Wrigley Field
Ivy-clad walls & manual scoreboard add retro charm to the 2nd oldest baseball stadium in the majors.
10:30 AM - 1:30 PM
$264
Day 4Architectural Marvels and Artistic Wonders
+

$64

·

$ 10

Chicago Marriott Downtown Magnificent Mile

Depart from your stay 🏨

9 - 11 min

~

Directions

Jay Pritzker Pavilion
Designed by architect Frank Gehry, this bandshell in Millennium Park hosts various musical events.
8:00 AM - 9:00 AM
Free
16 - 23 min

~

Directions

Buckingham Fountain
Among the world’s largest, Grant Park’s 3-level rococo fountain (1927) offers light & water shows.
9:30 AM - 10:30 AM
Free
9 - 14 min

~

Directions

The Art Institute of Chicago
Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
11:00 AM - 2:00 PM
$64
Day 5Botanical Oasis and Cultural Treasures
+

$75

·

$ 20

Chicago Marriott Downtown Magnificent Mile

Depart from your stay 🏨

24 - 29 min

~

Directions

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
17 - 21 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
18 - 22 min

~

Directions

Chicago Symphony Orchestra
Built in 1904, music complex that hosts the Chicago Symphony Orchestra & classical & jazz concerts.
12:00 PM - 2:00 PM
$75
Day 6Urban Oasis and Museum Marvels
+

$0

·

$ 15

Chicago Marriott Downtown Magnificent Mile

Depart from your stay 🏨

10 - 12 min

~

Directions

Millennium Park
24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.
8:00 AM - 10:00 AM
Free
9 - 11 min

~

Directions

Museum Campus
57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.
10:30 AM - 1:30 PM
Free

Budget breakdown: $621 In total

Activities & Food:$541
Transport:$80