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A Week in Chicago: Explore the Windy City's Best

Jason Burke

Jason Burke

3 Oct 2023

Embark on a thrilling 6-day journey through Chicago, IL, United States. Discover iconic landmarks, indulge in delicious cuisine, and immerse yourself in the vibrant culture of the Windy City.

Trip to Chicago

Day 1
+

$71

·

$ 5

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Depart from your stay 🏨

8 - 10 min

~

Directions

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Casual lodging offering a polished cocktail bar with city views, plus an indoor pool & free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
9 - 14 min

~

Directions

Kanela Breakfast Club
7:30 AM - 8:30 AM
•
$8
11 - 16 min

~

Directions

Navy Pier
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
9:00 AM - 11:00 AM
•
$31
4 - 6 min

~

Directions

Cupitol Coffee & Eatery
Cupitol is a new all-day​ lounge that brings together the best elements of a restaurant, a bakery, a cafe and an exclusive bar.
1:00 PM - 2:30 PM
•
$18
Buona
Quick casual restaurant featuring Original Italian Beef, Pizza, Burgers, Hot Dogs, Sandwiches and Salads
7:00 PM - 8:30 PM
•
$13
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Casual lodging offering a polished cocktail bar with city views, plus an indoor pool & free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
Day 2
+

$46

·

$ 5

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Depart from your stay 🏨

11 - 14 min

~

Directions

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Casual lodging offering a polished cocktail bar with city views, plus an indoor pool & free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
8 - 12 min

~

Directions

Ranalli's Lincoln Park
The Ranalli's family-owned business has been keeping Chicagoans well-fed for over 30 years. Starting on Lincoln Avenue in the 1970s, Ranalli's legendary food and around the world beer list, along with its famous outdoor patio, has become a favorite of both locals and tourists alike.
7:30 AM - 8:30 AM
•
$15
6 - 9 min

~

Directions

Lincoln Park Zoo
Small, free zoo with lions, primates, reptiles, a children's area & an interactive farm exhibit.
9:00 AM - 11:00 AM
•
Free
8 - 12 min

~

Directions

Chicago Pizza & Oven Grinder
1:00 PM - 2:30 PM
•
$12
Firecakes Donuts
7:00 PM - 8:30 PM
•
$19
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Casual lodging offering a polished cocktail bar with city views, plus an indoor pool & free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
Day 3
+

$75

·

$ 3

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Depart from your stay 🏨

8 - 10 min

~

Directions

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Casual lodging offering a polished cocktail bar with city views, plus an indoor pool & free Wi-Fi.
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
•
$7
8 - 11 min

~

Directions

Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
9:00 AM - 10:30 AM
•
$31
5 - 8 min

~

Directions

Garrett Popcorn Shops
1:00 PM - 2:30 PM
•
$12
Sweetgreen
Fresh salads, plates + grain bowls available for pickup and delivery every day, made in-house from scratch, using whole produce delivered that morning.
7:00 PM - 8:30 PM
•
$24
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Casual lodging offering a polished cocktail bar with city views, plus an indoor pool & free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
Day 4
+

$43

·

$ 5

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Depart from your stay 🏨

10 - 12 min

~

Directions

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Casual lodging offering a polished cocktail bar with city views, plus an indoor pool & free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
5 - 8 min

~

Directions

Wildberry Pancakes & Cafe
7:30 AM - 8:30 AM
•
$12
6 - 9 min

~

Directions

Millennium Park
24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.
9:00 AM - 11:00 AM
•
Free
3 - 4 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
•
$18
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
•
$13
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Casual lodging offering a polished cocktail bar with city views, plus an indoor pool & free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
Day 5
+

$104

·

$ 5

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Depart from your stay 🏨

14 - 17 min

~

Directions

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Casual lodging offering a polished cocktail bar with city views, plus an indoor pool & free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
12 - 17 min

~

Directions

Dmk
7:30 AM - 8:30 AM
•
$10
16 - 23 min

~

Directions

Shedd Aquarium
State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.
9:00 AM - 12:00 PM
•
$50
10 - 15 min

~

Directions

Victory Tap
Serving traditional Italian food since 1956 with a passion for traditional Italian dishes has created our fine menu of tried and true classics sure to impress anyones pallet.
1:00 PM - 2:30 PM
•
$24
Grant Park Bistro
7:00 PM - 8:30 PM
•
$20
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Casual lodging offering a polished cocktail bar with city views, plus an indoor pool & free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
Day 6
+

$93

·

$ 10

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Depart from your stay 🏨

20 - 24 min

~

Directions

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Casual lodging offering a polished cocktail bar with city views, plus an indoor pool & free Wi-Fi.
7:30 AM - 7:30 AM
•
Free
8 - 11 min

~

Directions

B'Gabs
Raw, vegan, gluten-free, soy-free, peanut-free, smoothie bar, juice bar, herbs, tea, essential oils
7:30 AM - 8:30 AM
•
$11
5 - 6 min

~

Directions

Museum of Science and Industry, Chicago
Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.
9:00 AM - 1:00 PM
•
$38
5 - 6 min

~

Directions

Plein Air Cafe & Eatery
1:30 PM - 3:00 PM
•
$20
Virtue Restaurant
7:00 PM - 8:30 PM
•
$24
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Casual lodging offering a polished cocktail bar with city views, plus an indoor pool & free Wi-Fi.
7:30 AM - 7:30 AM
•
Free

Budget breakdown: $463 In total

Activities & Food:$430
Transport:$33