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Discover the Best of Chicago in 5 Days

zay

1 Oct 2023

0

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

Tours & Activities

Viator Tours

Day 1

+

$139

·

$ 10

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

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

•

$63

8 - 10 min

~

Directions

Millennium Park

24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.

11:00 AM - 1:00 PM

•

Free

9 - 11 min

~

Directions

Grant Park Bistro

1:30 PM - 3:00 PM

•

$36

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

12 - 17 min

~

Directions

Garrett Popcorn Shops

2:00 PM - 3:30 PM

•

$24

Day 2

+

$155

·

$ 5

Osaka Sushi Express & Fresh Fruit Smoothies

7:30 AM - 8:30 AM

•

$30

8 - 11 min

~

Directions

Grant Park

312-acre centerpiece of Downtown housing some of the city's busiest attractions.

9:00 AM - 11:00 AM

•

Free

5 - 6 min

~

Directions

Willis Tower

Iconic, 110-story skyscraper featuring expansive views of Chicago from its 103rd-story Skydeck.

11:30 AM - 1:30 PM

•

$63

8 - 11 min

~

Directions

Garrett Popcorn Shops

2:00 PM - 3:30 PM

•

$24

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

•

$38

Day 3

+

$249

·

$ 10

Dmk

7:30 AM - 8:30 AM

•

$14

12 - 17 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

9 - 11 min

~

Directions

Cloud Gate

Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.

12:30 PM - 1:30 PM

•

Free

11 - 14 min

~

Directions

Doc B's Fresh Kitchen

2:00 PM - 3:30 PM

•

$24

7 - 10 min

~

Directions

360 CHICAGO

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

3:30 PM - 5:00 PM

•

$63

4 - 5 min

~

Directions

Cafecito

7:00 PM - 8:30 PM

•

$48

Day 4

+

$149

·

$ 5

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

•

$24

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

12 - 15 min

~

Directions

Navy Pier

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

11:30 AM - 1:30 PM

•

$63

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.

2:00 PM - 3:30 PM

•

$36

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

•

$26

Day 5

+

$183

·

$ 15

Wildberry Pancakes & Cafe

7:30 AM - 8:30 AM

•

$20

8 - 11 min

~

Directions

Riverwalk

Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.

9:00 AM - 11:00 AM

•

Free

8 - 11 min

~

Directions

The Chicago Theatre

French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.

11:30 AM - 1:30 PM

•

$75

18 - 22 min

~

Directions

Rootstock Wine & Beer Bar

2:00 PM - 3:30 PM

•

$48

6 - 8 min

~

Directions

Garfield Park Conservatory - Reservations Required

184-acre park with a swimming pool, fishing lagoon, athletic fields & tennis courts.

3:30 PM - 5:00 PM

•

Free

7 - 9 min

~

Directions

Flying Saucer

7:00 PM - 8:30 PM

•

$40

Budget breakdown: $918 In total

Activities & Food:$873

Transport:$45