6 Days in Chicago: Exploring the Windy City's Delights

Linda Darwish

7 Dec 2023

Join me on a thrilling 6-day adventure through the vibrant streets of Chicago. From iconic landmarks to mouthwatering deep-dish pizza, this itinerary is packed with excitement and unforgettable experiences. Get ready to immerse yourself in the rich culture, stunning architecture, and delicious cuisine of the Windy City!

Trip to Chicago

Tours & Activities

Viator Tours

Day 1Savory Delights and Cultural Marvels

$301

$ 5

Blends the bold flavors + savory spices found in Puerto Rico, South East Asia, China, Japan and Korea. Comfort foods from the motherland with a twist.

7:30 AM - 8:30 AM

•

$38

5 - 8 min

Directions

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

9:00 AM - 10:30 AM

•

$63

7 - 9 min

Directions

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

11:00 AM - 2:00 PM

•

$64

4 - 5 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.

2:30 PM - 4:00 PM

•

$72

12 - 17 min

Directions

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

4:00 PM - 5:00 PM

•

Free

12 - 17 min

Directions

Full-service restaurant.

1:30 PM - 3:00 PM

•

$64

Day 2Coffee, Pier Fun, and Museum Marvels

$160

$ 5

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

•

$46

10 - 15 min

Directions

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

9:00 AM - 11:00 AM

•

Free

10 - 12 min

Directions

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

11:30 AM - 2:30 PM

•

Free

9 - 14 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

3:00 PM - 4:30 PM

•

$56

7 - 10 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.

12:30 PM - 2:00 PM

•

$58

Day 3Vegan Eats, Science Wonders, and Pizza Pleasures

$237

$ 5

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

7:30 AM - 8:30 AM

•

$42

8 - 11 min

Directions

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

9:00 AM - 1:00 PM

•

$75

15 - 18 min

Directions

Full-service restaurant.

1:30 PM - 3:00 PM

•

$64

9 - 14 min

Directions

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

3:00 PM - 5:00 PM

•

Free

12 - 17 min

Directions

7:00 PM - 8:30 PM

•

$56

Day 4Burgers, Aquariums, and Museum Magic

$319

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

•

$44

12 - 17 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

16 - 23 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.

12:30 PM - 2:00 PM

•

$58

12 - 18 min

Directions

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

2:00 PM - 5:00 PM

•

$63

12 - 17 min

Directions

Polish/Italian. Pizza/pierogi Craft beer/polish vodkas

7:00 PM - 8:30 PM

•

$54

Day 5Park Strolls, Zoo Adventures, and Culinary Delights

$223

$ 10

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

•

$50

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

10 - 12 min

Directions

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

11:30 AM - 1:00 PM

•

$63

9 - 11 min

Directions

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

1:30 PM - 3:00 PM

•

$58

5 - 8 min

Directions