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Discover the Best of Chicago: 4-Day Itinerary

Elizabeth A

Elizabeth A

9 Nov 2023

Experience the vibrant city of Chicago with this exciting 4-day itinerary. Explore iconic landmarks, indulge in delicious cuisine, and immerse yourself in the rich culture of the Windy City.

Trip to Chicago

Day 1
+

$166

·

$ 5

Hampton Inn & Suites Chicago-Downtown

Depart from your stay 🏨

11 - 14 min

~

Directions

Crown Fountain
Public sculpture with 2 50-ft. LED towers & a reflecting pool, by Catalan artist Jaume Plensa.
8:00 AM - 9:00 AM
•
Free
3 - 4 min

~

Directions

Millennium Park
24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.
9:30 AM - 11:30 AM
•
Free
4 - 5 min

~

Directions

Jay Pritzker Pavilion
Designed by architect Frank Gehry, this bandshell in Millennium Park hosts various musical events.
12:00 PM - 1:00 PM
•
Free
7 - 10 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
1:30 PM - 3:00 PM
•
$72
4 - 5 min

~

Directions

Chicago Architecture Center
Nonprofit promoting the city's built environment through tours, exhibitions & events.
3:00 PM - 4:30 PM
•
$38
5 - 8 min

~

Directions

Giordano's
Famous Chicago-style deep dish pizza right in your neighborhood. Visit us for a family-friendly atmosphere and delicious food or order your meal online for pickup or delivery.
7:00 PM - 8:30 PM
•
$56
Day 2
+

$189

·

$ 15

Hampton Inn & Suites Chicago-Downtown

Depart from your stay 🏨

16 - 20 min

~

Directions

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
8:00 AM - 9:30 AM
•
$63
8 - 10 min

~

Directions

Museum of Contemporary Photography
Museum offering programs & events, with a U.S.-focused permanent collection & rotating exhibits.
10:00 AM - 11:00 AM
•
Free
7 - 10 min

~

Directions

Grant Park
312-acre centerpiece of Downtown housing some of the city's busiest attractions.
11:30 AM - 1:30 PM
•
Free
12 - 17 min

~

Directions

The Gage
We invite you to savor our delicious, upscale comfort food, fine wines, boutique beers and whiskeys while enjoying the relaxing ambience of our vintage decor.
2:00 PM - 3:30 PM
•
$56
12 - 17 min

~

Directions

Buckingham Fountain
Among the world’s largest, Grant Park’s 3-level rococo fountain (1927) offers light & water shows.
3:30 PM - 4:30 PM
•
Free
12 - 17 min

~

Directions

Lou Malnati's Pizzeria
Full-service restaurant.
7:00 PM - 8:30 PM
•
$70
Day 3
+

$170

·

$ 10

Hampton Inn & Suites Chicago-Downtown

Depart from your stay 🏨

12 - 17 min

~

Directions

Museum of Illusions Chicago
Immersive rooms with optical illusions & holograms designed to deceive the eye, popular for photos.
8:00 AM - 9:30 AM
•
$50
9 - 14 min

~

Directions

Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
10:00 AM - 12:00 PM
•
Free
12 - 15 min

~

Directions

Lincoln Park Conservatory
Thousands of exotic plants in an 1890 glass structure, plus outdoor gardens & fountains.
12:30 PM - 1:30 PM
•
Free
3 - 4 min

~

Directions

Mon Ami Gabi
2:00 PM - 3:30 PM
•
$64
5 - 8 min

~

Directions

Alfred Caldwell Lily Pool
This serene section of Lincoln Park stars a lily pool & also boasts lush landscaping & a pavilion.
3:30 PM - 4:30 PM
•
Free
9 - 14 min

~

Directions

Chicago Pizza & Oven Grinder
7:00 PM - 8:30 PM
•
$56
Day 4
+

$0

·

$ 15

Hampton Inn & Suites Chicago-Downtown

Depart from your stay 🏨

10 - 12 min

~

Directions

Navy Pier
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
8:00 AM - 10:00 AM
•
Free
11 - 14 min

~

Directions

Lincoln Park Zoo
Small, free zoo with lions, primates, reptiles, a children's area & an interactive farm exhibit.
10:30 AM - 12:30 PM
•
Free

Budget breakdown: $569 In total

Activities & Food:$524
Transport:$45