Background
Trip Planner Logo

Discover the Best of Chicago: 8-Day Itinerary

Enmanuel Abreu

Enmanuel Abreu

11 Oct 2023

Embark on an unforgettable 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
+

$141

·

$ 15

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
•
$16
6 - 8 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
•
$63
5 - 8 min

~

Directions

Cloud Gate
Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.
11:00 AM - 12:00 PM
•
Free
4 - 6 min

~

Directions

Wildberry Pancakes & Cafe
1:00 PM - 2:30 PM
•
$36
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
•
$26
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
+

$92

·

$ 10

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
•
$30
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
•
$24
Firecakes Donuts
7:00 PM - 8:30 PM
•
$38
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
+

$186

·

$ 15

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Depart from your stay 🏨

24 - 29 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
10 - 15 min

~

Directions

Two Hearted Queen
7:30 AM - 8:30 AM
•
$14
6 - 9 min

~

Directions

Wrigley Field
Ivy-clad walls & manual scoreboard add retro charm to the 2nd oldest baseball stadium in the majors.
9:00 AM - 12:00 PM
•
$100
6 - 8 min

~

Directions

PR Italian Bistro
Award Winning, Italian-inspired Global Cuisine. Chef Owned. Named one of Chicago's Best Bistros -CBS Chicago
1:00 PM - 2:30 PM
•
$24
The Chicago Diner, Lakeview
7:00 PM - 8:30 PM
•
$48
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
+

$149

·

$ 15

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
5 - 8 min

~

Directions

Intelligentsia Coffee
7:30 AM - 8:30 AM
•
$24
11 - 14 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
11 - 16 min

~

Directions

Navy Pier
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
11:30 AM - 1:30 PM
•
$63
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.
2:00 PM - 3:30 PM
•
$36
Buona
Quick casual restaurant featuring Original Italian Beef, Pizza, Burgers, Hot Dogs, Sandwiches and Salads
7:00 PM - 8:30 PM
•
$26
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
+

$171

·

$ 10

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Depart from your stay 🏨

19 - 23 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
4 - 6 min

~

Directions

Just Salad
7:30 AM - 8:30 AM
•
$20
6 - 9 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
5 - 8 min

~

Directions

Garrett Popcorn Shops
1:00 PM - 2:30 PM
•
$48
Cafecito
7:00 PM - 8:30 PM
•
$40
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
+

$96

·

$ 10

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Depart from your stay 🏨

21 - 26 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
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
•
$22
12 - 18 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
8 - 11 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
•
$40
Eleven City Diner
7:00 PM - 8:30 PM
•
$34
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 7
+

$186

·

$ 10

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
•
$18
14 - 21 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
•
$100
5 - 8 min

~

Directions

Grant Park Bistro
1:00 PM - 2:30 PM
•
$34
Eleven City Diner
7:00 PM - 8:30 PM
•
$34
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 8
+

$0

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Depart from your stay 🏨

Budget breakdown: $1105 In total

Activities & Food:$1020
Transport:$85