Chicago Adventure: 10 Days of Exploring the Windy City

Andre Pazmiño

28 Nov 2023

Embark on an epic 10-day journey through the vibrant streets of Chicago. Discover iconic landmarks, indulge in delicious cuisine, and immerse yourself in the city's rich culture. Get ready for an unforgettable adventure in the Windy City!

Trip to Chicago

Tours & Activities

Viator Tours

Day 1Queen's Quest and Urban Delights

$316

$ 5

7:30 AM - 8:30 AM

•

$16

10 - 15 min

Directions

Ivy-clad walls & manual scoreboard add retro charm to the 2nd oldest baseball stadium in the majors.

9:00 AM - 12:00 PM

•

$264

18 - 22 min

Directions

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

12:30 PM - 1:30 PM

•

Free

5 - 8 min

Directions

2:00 PM - 3:30 PM

•

$36

Day 2Culinary Delights and Sky-High Thrills

$179

$ 10

7:30 AM - 8:30 AM

•

$30

5 - 8 min

Directions

Garfield Park Conservatory - Reservations Required

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

9:00 AM - 10:30 AM

•

Free

11 - 14 min

Directions

103rd floor of the Willis Tower with clear observation boxes & views extending to four states.

11:00 AM - 12:30 PM

•

$63

16 - 20 min

Directions

1:00 PM - 2:30 PM

•

$24

7 - 10 min

Directions

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

2:30 PM - 4:00 PM

•

$63

Day 3Parks, Zoos, and Pier Fun

$38

$ 5

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

•

$14

8 - 12 min

Directions

Small, free zoo with lions, primates, reptiles, a children's area & an interactive farm exhibit.

9:00 AM - 11:00 AM

•

Free

14 - 17 min

Directions

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

11:30 AM - 1:30 PM

•

Free

11 - 16 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.

2:00 PM - 3:30 PM

•

$24

Day 4Breakfast Bliss and Riverwalk Strolls

$98

$ 5

7:30 AM - 8:30 AM

•

$24

6 - 9 min

Directions

Family museum on Navy Pier with lots of interactive exhibits, including many for young kids.

9:00 AM - 11:00 AM

•

$38

13 - 16 min

Directions

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

11:30 AM - 1:30 PM

•

Free

6 - 9 min

Directions

By Millenium Park at Lake and Michigan, Downtown Chicago restaurant Roti Modern Mediterranean offers a menu of deliciously fresh salads, bowls, & pitas

2:00 PM - 3:30 PM

•

$36

7 - 10 min

Directions

No time set

•

Free

Day 5Brunching, Museums, and Park Serenity

$68

$ 5

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

•

$20

10 - 15 min

Directions

57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.

9:00 AM - 12:00 PM

•

Free

6 - 8 min

Directions

Fresh salads, plates + grain bowls available for pickup and delivery every day, made in-house from scratch, using whole produce delivered that morning.

12:30 PM - 2:00 PM

•

$48

6 - 9 min

Directions

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

2:00 PM - 4:00 PM

•

Free

Day 6Gourmet Burgers and Aquatic Wonders

$162

$ 5

7:30 AM - 8:30 AM

•

$22

10 - 15 min

Directions

State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.

9:00 AM - 12:00 PM

•

$100

6 - 8 min

Directions

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

12:30 PM - 1:30 PM

•

Free

10 - 15 min

Directions

2:00 PM - 3:30 PM

•

$40

Day 7Donut Delights and Museum Marvels

$115

7:30 AM - 8:30 AM

•

$18

10 - 15 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 - 18 min

Directions

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

•

$34

Day 8Sushi Sensations and Artistic Treasures

$130

Osaka Sushi Express & Fresh Fruit Smoothies

7:30 AM - 8:30 AM

•

$30

8 - 11 min

Directions

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

9:00 AM - 11:00 AM

•

Free

9 - 14 min

Directions

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

11:30 AM - 2:30 PM

•

$64

6 - 9 min

Directions

3:00 PM - 4:30 PM

•

$36

Day 9Vegan Delights and Scientific Wonders

$141

$ 5

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

7:30 AM - 8:30 AM

•

$24

8 - 11 min

Directions

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

9:00 AM - 1:00 PM

•

$75

5 - 6 min

Directions

1:30 PM - 3:00 PM

•

$42

Day 10Park Picnics and Architectural Marvels

$200

$ 10

7:30 AM - 8:30 AM

•

$26

6 - 8 min

Directions

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

9:00 AM - 11:00 AM

•

Free

16 - 20 min

Directions

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

11:30 AM - 1:30 PM

•

$63

10 - 15 min

Directions

Fresh salads, plates + grain bowls available for pickup and delivery every day, made in-house from scratch, using whole produce delivered that morning.

2:00 PM - 3:30 PM

•

$36

6 - 9 min

Directions

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

3:30 PM - 5:30 PM

•

$75

Budget breakdown: $1496 In total

Activities & Food:$1446

Transport:$50