8 Days in the Windy City!

Frankie S

17 Jan 2024

Embark on an epic adventure through the vibrant streets of Chicago! From towering skyscrapers to world-class museums, this itinerary will take you on a whirlwind tour of the city's iconic landmarks and hidden gems. Get ready to immerse yourself in the rich culture, mouthwatering cuisine, and unforgettable experiences that the Windy City has to offer!

Trip to Chicago

Tours & Activities

Viator Tours

Day 1Savoring Saucy Delights and Soaring to New Heights

$493

$ 10

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

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

9:00 AM - 11:00 AM

•

$63

22 - 27 min

Directions

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

11:30 AM - 2:30 PM

•

$264

6 - 9 min

Directions

Award Winning, Italian-inspired Global Cuisine. Chef Owned. Named one of Chicago's Best Bistros -CBS Chicago

3:00 PM - 4:30 PM

•

$72

5 - 6 min

Directions

7:00 PM - 8:30 PM

•

$56

Day 2Indulging in Art and Architecture, and Basking in the Beauty of Buckingham Fountain

$217

$ 5

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

•

$46

7 - 10 min

Directions

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

9:00 AM - 10:30 AM

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$63

12 - 15 min

Directions

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

11:00 AM - 1:00 PM

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Free

13 - 20 min

Directions

1:30 PM - 3:00 PM

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$56

19 - 28 min

Directions

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

3:00 PM - 4:00 PM

•

Free

10 - 15 min

Directions

Visit Buddy Guy's Legends to experience the finest blues seven nights a week, enjoy southern Cajun soul food, and behold a major archive of blues.

7:00 PM - 8:30 PM

•

$52

Day 3Exploring the Magnificent Mile and Savoring Mediterranean Delights

$337

$ 10

Take a culinary tour of Barcelona right on Michigan Avenue at Mercat a la Planxa, a Chicago Tapas Restaurant by Iron Chef Jose Garces!

7:30 AM - 8:30 AM

•

$42

5 - 8 min

Directions

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

9:00 AM - 11:00 AM

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Free

8 - 10 min

Directions

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

11:30 AM - 1:30 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

2:00 PM - 3:30 PM

•

$64

4 - 6 min

Directions

Long-standing drawbridge honoring a founder of Chicago & decorated with sculptures & plaques.

3:30 PM - 4:30 PM

•

Free

5 - 8 min

Directions

7:00 PM - 8:30 PM

•

$56

18 - 22 min

Directions

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

2:00 PM - 5:00 PM

•

$100

Day 4Unleashing Your Inner Scientist and Savoring Eclectic Cuisine

$253

$ 5

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

7:30 AM - 8:30 AM

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$44

8 - 11 min

Directions

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

9:00 AM - 1:00 PM

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$75

14 - 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.

7:00 PM - 8:30 PM

•

$62

3 - 4 min

Directions

Public sculpture with 2 50-ft. LED towers & a reflecting pool, by Catalan artist Jaume Plensa.

3:00 PM - 4:00 PM

•

Free

4 - 5 min

Directions

Flat Top Stir-Fry Grill is a create-your-own stir-fry restaurant featuring fresh ingredients, house made sauces for a fun, fresh and interactive dining experience.

1:00 PM - 2:30 PM

•

$72

Day 5Feasting on Fluffy Pancakes and Diving into the Depths of the Ocean

$160

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

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$50

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

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Free

11 - 16 min

Directions

12:30 PM - 2:00 PM

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$58

6 - 9 min

Directions

Visit Buddy Guy's Legends to experience the finest blues seven nights a week, enjoy southern Cajun soul food, and behold a major archive of blues.

7:00 PM - 8:30 PM

•

$52

Day 6Burgers, Museums, and Pancakes: A Perfect Day in Chicago

$209

$ 5

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

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$36

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

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$63

8 - 10 min

Directions

12:30 PM - 2:00 PM

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$52

5 - 8 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

5 - 8 min

Directions

Famous Chicago-style deep dish pizza right in your neighborhood. Visit us for a family-friendly atmosphere and delicious food or order your meal online for pickup or delivery.

1:30 PM - 3:00 PM

•

$58

Day 7Discovering Lincoln Park's Treasures and Savoring Deep-Dish Pizza

$235

$ 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

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$42

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

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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

10 - 12 min

Directions

Famous Chicago-style deep dish pizza right in your neighborhood. Visit us for a family-friendly atmosphere and delicious food or order your meal online for pickup or delivery.

1:30 PM - 3:00 PM

•

$58

3 - 4 min

Directions

Free art & shows in an 1897 Beaux-Arts building with vaulted lobby, mosaics & 2 stained-glass domes.

3:00 PM - 4:00 PM

•

Free

4 - 6 min

Directions

7:00 PM - 8:30 PM

•

$72

Day 8Coffee, Pier Fun, and Reflections in The Bean

$184

$ 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

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$50

10 - 15 min

Directions

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

9:00 AM - 11:00 AM

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Free

10 - 12 min

Directions

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

11:30 AM - 12:30 PM

•

Free

6 - 9 min

Directions

Flat Top Stir-Fry Grill is a create-your-own stir-fry restaurant featuring fresh ingredients, house made sauces for a fun, fresh and interactive dining experience.

1:00 PM - 2:30 PM

•

$72

3 - 4 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.

7:00 PM - 8:30 PM

•

$62

Budget breakdown: $2136 In total

Activities & Food:$2086

Transport:$50