Back

8-Day Chicago Adventure: Explore the Windy City's Best Sights and Tastes

DANIEL HERNANDEZ

3 Oct 2023

0

Embark on an unforgettable 8-day journey through Chicago, IL, and discover the city's iconic landmarks, mouthwatering cuisine, and vibrant culture. From the magnificent Buckingham Fountain to the mesmerizing Cloud Gate, immerse yourself in the beauty of Millennium Park. Indulge in delectable meals at renowned eateries like Sweetgreen, Wildberry Pancakes & Cafe, and more. Get ready for an incredible solo adventure in the Windy City!

Trip to Chicago

Tours & Activities

Viator Tours

Day 1

+

$84

Osaka Sushi Express & Fresh Fruit Smoothies

7:30 AM - 8:30 AM

•

$32

8 - 11 min

~

Directions

Buckingham Fountain

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

9:00 AM - 10:00 AM

•

Free

11 - 16 min

~

Directions

Crown Fountain

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

10:30 AM - 11:30 AM

•

Free

3 - 4 min

~

Directions

Cloud Gate

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

12:00 PM - 1:00 PM

•

Free

4 - 5 min

~

Directions

Chicago Cultural Center

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

1:30 PM - 2:30 PM

•

Free

4 - 5 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

•

$52

Day 2

+

$281

Just Salad

7:30 AM - 8:30 AM

•

$60

4 - 6 min

~

Directions

The Art Institute of Chicago

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

9:00 AM - 12:00 PM

•

$125

5 - 8 min

~

Directions

Millennium Park

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

12:30 PM - 2:30 PM

•

Free

5 - 8 min

~

Directions

Wildberry Pancakes & Cafe

7:00 PM - 8:30 PM

•

$96

Day 3

+

$249

·

$ 10

Garrett Popcorn Shops

7:30 AM - 8:30 AM

•

$28

4 - 6 min

~

Directions

Civic Opera House

North America's 2nd-largest opera venue has over 3,500 seats & houses the Lyric Opera of Chicago.

9:00 AM - 10:30 AM

•

Free

5 - 8 min

~

Directions

Willis Tower

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

11:00 AM - 1:00 PM

•

$125

9 - 11 min

~

Directions

Jay Pritzker Pavilion

Designed by architect Frank Gehry, this bandshell in Millennium Park hosts various musical events.

1:30 PM - 2:30 PM

•

Free

4 - 5 min

~

Directions

Wildberry Pancakes & Cafe

7:00 PM - 8:30 PM

•

$96

Day 4

+

$375

·

$ 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

•

$48

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

•

$125

5 - 6 min

~

Directions

The Chicago Theatre

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

11:00 AM - 1:00 PM

•

$150

4 - 5 min

~

Directions

Roti Modern Mediterranean

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

•

$52

Day 5

+

$395

·

$ 10

B'Gabs

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

7:30 AM - 8:30 AM

•

$40

8 - 11 min

~

Directions

Museum of Science and Industry, Chicago

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

9:00 AM - 1:00 PM

•

$150

24 - 29 min

~

Directions

360 CHICAGO

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

1:30 PM - 3:00 PM

•

$125

7 - 10 min

~

Directions

Doc B's Fresh Kitchen

7:00 PM - 8:30 PM

•

$80

Day 6

+

$140

Yolk

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

•

$44

10 - 15 min

~

Directions

Museum Campus

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

9:00 AM - 12:00 PM

•

Free

12 - 18 min

~

Directions

Victory Tap

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.

7:00 PM - 8:30 PM

•

$96

Day 7

+

$229

·

$ 10

Dmk

7:30 AM - 8:30 AM

•

$36

10 - 15 min

~

Directions

Field Museum

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

9:00 AM - 12:00 PM

•

$125

20 - 24 min

~

Directions

Lincoln Park Zoo

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

12:30 PM - 2:30 PM

•

Free

6 - 9 min

~

Directions

Chicago Pizza & Oven Grinder

7:00 PM - 8:30 PM

•

$68

Day 8

+

$273

·

$ 10

Kanela Breakfast Club

7:30 AM - 8:30 AM

•

$60

9 - 14 min

~

Directions

Navy Pier

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

9:00 AM - 11:00 AM

•

$125

9 - 11 min

~

Directions

Grant Park

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

11:30 AM - 1:30 PM

•

Free

7 - 10 min

~

Directions

Grant Park Bistro

7:00 PM - 8:30 PM

•

$88

Budget breakdown: $2076 In total

Activities & Food:$2026

Transport:$50