Background
Trip Planner Logo

8 Days in the Windy City!

Danielle Dykhouse

Danielle Dykhouse

30 Dec 2023

Join me on an epic adventure through the vibrant streets of Chicago! From iconic landmarks to hidden gems, this blog will take you on a whirlwind tour of the city's rich history, stunning architecture, and mouthwatering cuisine.

Trip to Chicago

Day 1Parks, Science, and Music
+

$250

·

$ 30

Jackson (Andrew) Park
540-plus-acre city park featuring a beach, gardens & indoor/outdoor fitness facilities.
8:00 AM - 10:00 AM
•
Free
6 - 8 min

~

Directions

Museum of Science and Industry, Chicago
Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.
10:30 AM - 2:30 PM
•
$150
18 - 22 min

~

Directions

Jay Pritzker Pavilion
Designed by architect Frank Gehry, this bandshell in Millennium Park hosts various musical events.
3:00 PM - 4:00 PM
•
Free
33 - 40 min

~

Directions

Brookfield Zoo
Lions, tigers, dolphins & more frolic in natural indoor & outdoor settings at this wildlife park.
No time set
•
$100
Day 2Parks, Fountains, and Museums
+

$125

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
11 - 16 min

~

Directions

Buckingham Fountain
Among the world’s largest, Grant Park’s 3-level rococo fountain (1927) offers light & water shows.
10:30 AM - 11:30 AM
•
Free
4 - 5 min

~

Directions

Grant Park
312-acre centerpiece of Downtown housing some of the city's busiest attractions.
12:00 PM - 2:00 PM
•
Free
10 - 15 min

~

Directions

Field Museum
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
2:30 PM - 5:30 PM
•
$125
Day 3Discovering the Museum Campus
+

$200

Museum Campus
57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.
8:00 AM - 11:00 AM
•
Free
4 - 6 min

~

Directions

Shedd Aquarium
State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.
11:30 AM - 2:30 PM
•
$200
Day 4Theatres, Art, and Symphony
+

$428

The Chicago Theatre
French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.
8:00 AM - 10:00 AM
•
$150
8 - 12 min

~

Directions

Crown Fountain
Public sculpture with 2 50-ft. LED towers & a reflecting pool, by Catalan artist Jaume Plensa.
10:30 AM - 11:30 AM
•
Free
3 - 4 min

~

Directions

The Art Institute of Chicago
Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
12:00 PM - 3:00 PM
•
$128
3 - 4 min

~

Directions

Chicago Symphony Orchestra
Built in 1904, music complex that hosts the Chicago Symphony Orchestra & classical & jazz concerts.
3:30 PM - 5:30 PM
•
$150
Day 5Parks, Towers, and Museums
+

$250

·

$ 40

Ping Tom Memorial Park
Chinatown park on the Chicago River with Chinese-style landscaping, a playground & kayak rentals.
8:00 AM - 9:30 AM
•
Free
9 - 11 min

~

Directions

Willis Tower
Iconic, 110-story skyscraper featuring expansive views of Chicago from its 103rd-story Skydeck.
10:00 AM - 12:00 PM
•
$125
11 - 14 min

~

Directions

WNDR Museum
Multi-sensory, contemporary installations by artists including Yayoi Kusama.
12:30 PM - 2:00 PM
•
$125
12 - 15 min

~

Directions

National Museum of Mexican Art
Some 18,000 paintings, photographs, sculptures & more are housed at this art museum.
2:30 PM - 4:00 PM
•
Free
22 - 27 min

~

Directions

Humboldt (Alexander Von) Park
Suburban recreational area with soccer & baseball fields, tennis courts & playgrounds, plus a beach.
4:30 PM - 6:30 PM
•
Free
Day 6Sky-high Views and Cultural Delights
+

$125

·

$ 20

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
8:00 AM - 9:30 AM
•
$125
8 - 10 min

~

Directions

Cloud Gate
Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.
10:00 AM - 11:00 AM
•
Free
4 - 5 min

~

Directions

Chicago Cultural Center
Free art & shows in an 1897 Beaux-Arts building with vaulted lobby, mosaics & 2 stained-glass domes.
11:30 AM - 12:30 PM
•
Free
8 - 12 min

~

Directions

The Wrigley Building
Beloved 1924 addition to the city skyline, whose clock tower stands 425 ft above street level.
1:00 PM - 2:00 PM
•
Free
15 - 18 min

~

Directions

Lincoln Park Zoo
Small, free zoo with lions, primates, reptiles, a children's area & an interactive farm exhibit.
2:30 PM - 4:30 PM
•
Free
5 - 8 min

~

Directions

Lincoln Park Conservatory
Thousands of exotic plants in an 1890 glass structure, plus outdoor gardens & fountains.
5:00 PM - 6:00 PM
•
Free
Day 7Pier Fun and Artistic Marvels
+

$200

·

$ 20

Navy Pier
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
8:00 AM - 10:00 AM
•
Free
9 - 11 min

~

Directions

Museum Of Contemporary Art Chicago
Downtown museum showcasing post-World War II paintings, sculptures, photos, videos & performances.
10:30 AM - 12:00 PM
•
$75
5 - 8 min

~

Directions

360 CHICAGO
Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.
12:30 PM - 2:00 PM
•
$125
5 - 6 min

~

Directions

North Avenue Beach
2:30 PM - 4:30 PM
•
Free
Day 8Sports, Bridges, and Riverwalk
+

$603

·

$ 20

Wrigley Field
Ivy-clad walls & manual scoreboard add retro charm to the 2nd oldest baseball stadium in the majors.
8:00 AM - 11:00 AM
•
$528
18 - 22 min

~

Directions

DuSable Bridge
Long-standing drawbridge honoring a founder of Chicago & decorated with sculptures & plaques.
11:30 AM - 12:30 PM
•
Free
3 - 4 min

~

Directions

Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
1:00 PM - 3:00 PM
•
Free
13 - 16 min

~

Directions

Chicago Children's Museum
Family museum on Navy Pier with lots of interactive exhibits, including many for young kids.
3:30 PM - 5:30 PM
•
$75

Budget breakdown: $2311 In total

Activities & Food:$2181
Transport:$130