5 Days in the Windy City

Lucia Carrizo

21 Nov 2023

Embark on an unforgettable journey through the vibrant streets of Chicago. Discover iconic landmarks, savor delectable cuisine, and immerse yourself in the city's rich culture. Get ready for an adventure of a lifetime!

Trip to Chicago

Tours & Activities

Viator Tours

Day 1Subs, Art, and Clouds: Day 1 in Chicago

$232

$ 5

Pendry Chicago

Depart from your stay 🏨

5 - 6 min

Directions

We have been serving our delicious subs, soups and salads for over 50 Years! We will continue to do so along with a few new additions to the Fontano’s menu. ...

7:30 AM - 8:30 AM

•

$38

4 - 5 min

Directions

Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.

9:00 AM - 12:00 PM

•

$64

5 - 8 min

Directions

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

12:30 PM - 1:30 PM

•

Free

4 - 6 min

Directions

2:00 PM - 3:30 PM

•

$72

2 - 3 min

Directions

We invite you to savor our delicious, upscale comfort food, fine wines, boutique beers and whiskeys while enjoying the relaxing ambience of our vintage decor.

1:00 PM - 2:30 PM

•

$58

Day 2Pancakes, Parks, and Popcorn: Day 2 in Chicago

$229

$ 5

Pendry Chicago

Depart from your stay 🏨

4 - 6 min

Directions

7:30 AM - 8:30 AM

•

$46

5 - 8 min

Directions

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

9:00 AM - 11:00 AM

•

Free

6 - 8 min

Directions

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

2:00 PM - 3:30 PM

•

$56

8 - 11 min

Directions

Urban American tavern in Chicago's Block 37

12:30 PM - 2:00 PM

•

$64

Day 3Burgers, Museums, and Theatres: Day 3 in Chicago

$300

$ 10

Pendry Chicago

Depart from your stay 🏨

9 - 11 min

Directions

American Ranchers know a thing or two about beef. When they tell us that Prime is the best, we just go with the flow and serve up the biggest, baddest Prime burgers around.

7:30 AM - 8:30 AM

•

$42

8 - 12 min

Directions

State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.

9:00 AM - 12:00 PM

•

$63

12 - 15 min

Directions

Urban American tavern in Chicago's Block 37

12:30 PM - 2:00 PM

•

$64

4 - 5 min

Directions

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

2:00 PM - 4:00 PM

•

$75

4 - 5 min

Directions

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

•

$56

Day 4Coffee, Piers, and Pizza: Day 4 in Chicago

$154

$ 15

Pendry Chicago

Depart from your stay 🏨

12 - 18 min

Directions

Cupitol is a new all-day lounge that brings together the best elements of a restaurant, a bakery, a cafe and an exclusive bar.

7:30 AM - 8:30 AM

•

$44

10 - 15 min

Directions

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

9:00 AM - 11:00 AM

•

Free

7 - 9 min

Directions

Among the world’s largest, Grant Park’s 3-level rococo fountain (1927) offers light & water shows.

11:30 AM - 12:30 PM

•

Free

12 - 17 min

Directions

We invite you to savor our delicious, upscale comfort food, fine wines, boutique beers and whiskeys while enjoying the relaxing ambience of our vintage decor.

1:00 PM - 2:30 PM

•

$58

7 - 9 min

Directions

Full-service restaurant.

7:00 PM - 8:30 PM

•

$52

Day 5Vegan Delights, Science Wonders, and Park Strolls: Day 5 in Chicago

$235

$ 15

Pendry Chicago

Depart from your stay 🏨

18 - 22 min

Directions

Raw, vegan, gluten-free, soy-free, peanut-free, smoothie bar, juice bar, herbs, tea, essential oils

7:30 AM - 8:30 AM

•

$50

8 - 11 min

Directions

Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.

9:00 AM - 1:00 PM

•

$75

13 - 16 min

Directions

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

1:30 PM - 3:00 PM

•

$58

9 - 14 min

Directions

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

3:00 PM - 5:00 PM

•

Free

9 - 14 min

Directions

Full-service restaurant.

7:00 PM - 8:30 PM

•

$52

Budget breakdown: $1199 In total

Activities & Food:$1149

Transport:$50