Background
Trip Planner Logo

A Week in Chicago: Exploring the Windy City

Cristina G. Montepeque

Cristina G. Montepeque

8 Oct 2023

Join me on a thrilling 7-day adventure in Chicago, IL. Discover iconic landmarks, indulge in delicious cuisine, and immerse yourself in the vibrant culture of the Windy City.

Day 1
+

$99

Willis Tower
Iconic, 110-story skyscraper featuring expansive views of Chicago from its 103rd-story Skydeck.
8:00 AM - 10:00 AM
$63
8 - 11 min

~

Directions

Garrett Popcorn Shops
1:00 PM - 2:30 PM
$36
Day 2
+

$87

The Art Institute of Chicago
Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
8:00 AM - 11:00 AM
$63
7 - 10 min

~

Directions

Cafecito
1:00 PM - 2:30 PM
$24
Day 3
+

$87

·

$ 5

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
8:00 AM - 9:30 AM
$63
6 - 8 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
5 - 8 min

~

Directions

Wildberry Pancakes & Cafe
1:00 PM - 2:30 PM
$24
Day 4
+

$36

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
6 - 9 min

~

Directions

Sweetgreen
Fresh salads, plates + grain bowls available for pickup and delivery every day, made in-house from scratch, using whole produce delivered that morning.
1:00 PM - 2:30 PM
$36
Day 5
+

$123

·

$ 5

Museum of Science and Industry, Chicago
Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.
8:00 AM - 12:00 PM
$75
5 - 6 min

~

Directions

Plein Air Cafe & Eatery
1:00 PM - 2:30 PM
$48
Day 6
+

$115

The Chicago Theatre
French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.
8:00 AM - 10:00 AM
$75
4 - 5 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
1:00 PM - 2:30 PM
$40
Day 7
+

$34

Grant Park
312-acre centerpiece of Downtown housing some of the city's busiest attractions.
8:00 AM - 10:00 AM
Free
7 - 10 min

~

Directions

Grant Park Bistro
1:00 PM - 2:30 PM
$34

Budget breakdown: $590 In total

Activities & Food:$580
Transport:$10