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Discover the Best of Chicago: 9-Day Itinerary

Patricia Granadino

13 Oct 2023

0

Embark on an unforgettable journey through the vibrant city of Chicago with this exciting 9-day itinerary. Explore iconic landmarks, indulge in delicious cuisine, and immerse yourself in the rich culture of the Windy City.

Trip to Chicago

Tours & Activities

Viator Tours

Day 1

+

$50

Wildberry Pancakes & Cafe

7:30 AM - 8:30 AM

•

$8

5 - 8 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

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

•

$18

3 - 4 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

•

$24

Day 2

+

$46

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

8 - 12 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

6 - 9 min

~

Directions

Chicago Pizza & Oven Grinder

1:00 PM - 2:30 PM

•

$12

8 - 12 min

~

Directions

Firecakes Donuts

7:00 PM - 8:30 PM

•

$19

Day 3

+

$81

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

7 - 10 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

8 - 11 min

~

Directions

Garrett Popcorn Shops

7:00 PM - 8:30 PM

•

$22

5 - 8 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.

7:00 PM - 8:30 PM

•

$20

Day 4

+

$75

Kanela Breakfast Club

7:30 AM - 8:30 AM

•

$12

9 - 14 min

~

Directions

Navy Pier

Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.

9:00 AM - 11:00 AM

•

$31

11 - 16 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

4 - 6 min

~

Directions

Buona

Quick casual restaurant featuring Original Italian Beef, Pizza, Burgers, Hot Dogs, Sandwiches and Salads

7:00 PM - 8:30 PM

•

$13

Day 5

+

$86

·

$ 3

Doc B's Fresh Kitchen

7:30 AM - 8:30 AM

•

$10

7 - 10 min

~

Directions

360 CHICAGO

Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.

9:00 AM - 10:30 AM

•

$31

9 - 11 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

6 - 9 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

•

$24

8 - 12 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.

7:00 PM - 8:30 PM

•

$20

Day 6

+

$55

·

$ 8

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

6 - 8 min

~

Directions

Jackson (Andrew) Park

540-plus-acre city park featuring a beach, gardens & indoor/outdoor fitness facilities.

9:00 AM - 11:00 AM

•

Free

8 - 10 min

~

Directions

Plein Air Cafe & Eatery

1:00 PM - 2:30 PM

•

$20

5 - 6 min

~

Directions

The Promontory

7:00 PM - 8:30 PM

•

$24

Day 7

+

$0

Day 8

+

$87

Just Salad

7:30 AM - 8:30 AM

•

$15

4 - 6 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

•

$31

7 - 10 min

~

Directions

Cafecito

1:00 PM - 2:30 PM

•

$18

5 - 8 min

~

Directions

Garrett Popcorn Shops

7:00 PM - 8:30 PM

•

$22

Day 9

+

$100

·

$ 3

Two Hearted Queen

7:30 AM - 8:30 AM

•

$12

10 - 15 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

•

$50

6 - 9 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

•

$21

6 - 8 min

~

Directions

The Chicago Diner, Lakeview

7:00 PM - 8:30 PM

•

$17

Budget breakdown: $590 In total

Activities & Food:$577

Transport:$13