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Chicago Adventure: 5-Day Itinerary

David Picciotto

David Picciotto

16 Oct 2023

Embark on a thrilling 5-day journey through the vibrant city of Chicago. Explore iconic landmarks, indulge in delicious cuisine, and immerse yourself in the rich culture of the Windy City.

Trip to Chicago

Day 1
+

$167

·

$ 20

The Congress Plaza Hotel & Convention Center

Depart from your stay 🏨

10 - 12 min

~

Directions

The Congress Plaza Hotel & Convention Center
Elegant 1893 landmark with lake views, elegant quarters & conference facilities, plus a barbershop.
7:30 AM - 7:30 AM
•
Free
9 - 14 min

~

Directions

Kanela Breakfast Club
7:30 AM - 8:30 AM
•
$16
12 - 15 min

~

Directions

Navy Pier
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
9:00 AM - 11:00 AM
•
$63
13 - 16 min

~

Directions

360 CHICAGO
Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.
11:30 AM - 1:00 PM
•
$63
8 - 11 min

~

Directions

Jay Pritzker Pavilion
Designed by architect Frank Gehry, this bandshell in Millennium Park hosts various musical events.
1:30 PM - 2:30 PM
•
Free
6 - 9 min

~

Directions

Crown Fountain
Public sculpture with 2 50-ft. LED towers & a reflecting pool, by Catalan artist Jaume Plensa.
3:00 PM - 4:00 PM
•
Free
Wildberry Pancakes & Cafe
7:00 PM - 8:30 PM
•
$26
The Congress Plaza Hotel & Convention Center
Elegant 1893 landmark with lake views, elegant quarters & conference facilities, plus a barbershop.
7:30 AM - 7:30 AM
•
Free
Day 2
+

$131

The Congress Plaza Hotel & Convention Center

Depart from your stay 🏨

6 - 9 min

~

Directions

The Congress Plaza Hotel & Convention Center
Elegant 1893 landmark with lake views, elegant quarters & conference facilities, plus a barbershop.
7:30 AM - 7:30 AM
•
Free
4 - 6 min

~

Directions

Just Salad
7:30 AM - 8:30 AM
•
$30
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.
9:00 AM - 12:00 PM
•
$63
11 - 16 min

~

Directions

Millennium Park
24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.
12:30 PM - 2:30 PM
•
Free
10 - 15 min

~

Directions

Buckingham Fountain
Among the world’s largest, Grant Park’s 3-level rococo fountain (1927) offers light & water shows.
3:00 PM - 4:00 PM
•
Free
Grant Park Bistro
7:00 PM - 8:30 PM
•
$38
The Congress Plaza Hotel & Convention Center
Elegant 1893 landmark with lake views, elegant quarters & conference facilities, plus a barbershop.
7:30 AM - 7:30 AM
•
Free
Day 3
+

$125

·

$ 15

The Congress Plaza Hotel & Convention Center

Depart from your stay 🏨

12 - 15 min

~

Directions

The Congress Plaza Hotel & Convention Center
Elegant 1893 landmark with lake views, elegant quarters & conference facilities, plus a barbershop.
7:30 AM - 7:30 AM
•
Free
7 - 10 min

~

Directions

Lou Mitchell's Restaurant & Bakery
Lou Mitchell’s is not only a classic Chicago icon, but our food is recognized both nationally and internationally with endless accolades. Among the list are USA Today, American Way, newspapers, magazines, food critics, television. It’s a must see place.
7:30 AM - 8:30 AM
•
$14
9 - 11 min

~

Directions

Willis Tower
Iconic, 110-story skyscraper featuring expansive views of Chicago from its 103rd-story Skydeck.
9:00 AM - 11:00 AM
•
$63
3 - 4 min

~

Directions

The Wrigley Building
Beloved 1924 addition to the city skyline, whose clock tower stands 425 ft above street level.
11:30 AM - 12:30 PM
•
Free
5 - 8 min

~

Directions

Tribune Tower
Neo-Gothic skyscraper influenced by Rouen Cathedral & decorated with rocks from world landmarks.
1:00 PM - 2:00 PM
•
Free
6 - 9 min

~

Directions

Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
2:30 PM - 4:30 PM
•
Free
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
•
$48
The Congress Plaza Hotel & Convention Center
Elegant 1893 landmark with lake views, elegant quarters & conference facilities, plus a barbershop.
7:30 AM - 7:30 AM
•
Free
Day 4
+

$200

·

$ 20

The Congress Plaza Hotel & Convention Center

Depart from your stay 🏨

25 - 30 min

~

Directions

The Congress Plaza Hotel & Convention Center
Elegant 1893 landmark with lake views, elegant quarters & conference facilities, plus a barbershop.
7:30 AM - 7:30 AM
•
Free
7 - 9 min

~

Directions

Kaufman's Bagel & Delicatessen
7:30 AM - 8:30 AM
•
$24
43 - 52 min

~

Directions

Illinois Holocaust Museum & Education Center
Powerful museum dedicated to the Holocaust & its survivors, with an interactive youth exhibition.
9:00 AM - 11:00 AM
•
$38
27 - 33 min

~

Directions

Frank Lloyd Wright Home & Studio
Home & studio of the famous architect, with guided tours focused on his early career.
11:30 AM - 1:00 PM
•
$50
8 - 11 min

~

Directions

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
1:30 PM - 3:00 PM
•
$63
Garrett Popcorn Shops
7:00 PM - 8:30 PM
•
$26
The Congress Plaza Hotel & Convention Center
Elegant 1893 landmark with lake views, elegant quarters & conference facilities, plus a barbershop.
7:30 AM - 7:30 AM
•
Free
Day 5
+

$135

·

$ 15

The Congress Plaza Hotel & Convention Center

Depart from your stay 🏨

8 - 11 min

~

Directions

The Congress Plaza Hotel & Convention Center
Elegant 1893 landmark with lake views, elegant quarters & conference facilities, plus a barbershop.
7:30 AM - 7:30 AM
•
Free
10 - 15 min

~

Directions

Yolk
YOLK, created by founder Taki Kastanis in 2006, has evolved into Chicago's #1 breakfast hot spot. Follow us on Twitter and Instagram @EatYolk #EatYolk
7:30 AM - 8:30 AM
•
$20
12 - 15 min

~

Directions

Museum Campus
57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.
9:00 AM - 12:00 PM
•
Free
5 - 6 min

~

Directions

Museum of Science and Industry, Chicago
Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.
12:30 PM - 4:30 PM
•
$75
Plein Air Cafe & Eatery
7:00 PM - 8:30 PM
•
$40
The Congress Plaza Hotel & Convention Center
Elegant 1893 landmark with lake views, elegant quarters & conference facilities, plus a barbershop.
7:30 AM - 7:30 AM
•
Free

Budget breakdown: $827 In total

Activities & Food:$757
Transport:$70