8 Days in the Windy City

Jay Campbell

27 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 1Bridges, Bean, and Theatrical Dreams

$227

Homewood Suites by Hilton Chicago-Downtown

Depart from your stay 🏨

6 - 9 min

Directions

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

8:00 AM - 9:00 AM

•

Free

8 - 12 min

Directions

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

9:30 AM - 10:30 AM

•

Free

4 - 5 min

Directions

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

11:00 AM - 12:00 PM

•

Free

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

12:30 PM - 2:00 PM

•

$54

4 - 5 min

Directions

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

2:00 PM - 4:00 PM

•

$113

4 - 6 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

•

$60

Day 2Sky-high Thrills and Lakeside Delights

$190

$ 15

Homewood Suites by Hilton Chicago-Downtown

Depart from your stay 🏨

11 - 16 min

Directions

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

8:00 AM - 9:30 AM

•

$94

10 - 12 min

Directions

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

10:00 AM - 12:00 PM

•

Free

8 - 10 min

Directions

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

12:30 PM - 1:30 PM

•

Free

6 - 9 min

Directions

2:00 PM - 3:30 PM

•

$36

4 - 5 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

•

$60

Day 3Zoo Adventures and Baseball Fever

$504

$ 30

Homewood Suites by Hilton Chicago-Downtown

Depart from your stay 🏨

13 - 16 min

Directions

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

8:00 AM - 10:00 AM

•

Free

20 - 24 min

Directions

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

10:30 AM - 1:30 PM

•

$396

6 - 9 min

Directions

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

2:00 PM - 3:30 PM

•

$36

6 - 8 min

Directions

7:00 PM - 8:30 PM

•

$72

Day 4Riverfront Strolls and Towering Views

$187

$ 38

Homewood Suites by Hilton Chicago-Downtown

Depart from your stay 🏨

8 - 11 min

Directions

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

8:00 AM - 10:00 AM

•

Free

11 - 14 min

Directions

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

10:30 AM - 12:30 PM

•

$94

33 - 40 min

Directions

1:00 PM - 2:30 PM

•

$54

7 - 9 min

Directions

Baha'i temple, one of 8 in the world, featuring a 135-ft white-stone dome completed in 1953.

2:30 PM - 4:00 PM

•

Free

9 - 11 min

Directions

7:00 PM - 8:30 PM

•

$39

Day 5Science Wonders and Fountain Fantasies

$224

$ 23

Homewood Suites by Hilton Chicago-Downtown

Depart from your stay 🏨

19 - 23 min

Directions

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

8:00 AM - 12:00 PM

•

$113

12 - 15 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

7:00 PM - 8:30 PM

•

$51

11 - 16 min

Directions

7:00 PM - 8:30 PM

•

$60

Day 6Artistic Masterpieces and Urban Oasis

$228

$ 15

Homewood Suites by Hilton Chicago-Downtown

Depart from your stay 🏨

10 - 12 min

Directions

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

8:00 AM - 11:00 AM

•

$96

5 - 8 min

Directions

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

11:30 AM - 1:30 PM

•

Free

6 - 9 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

•

$60

8 - 11 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.

7:00 PM - 8:30 PM

•

$72

Day 7Museum Marvels and Park Escapes

$102

$ 15

Homewood Suites by Hilton Chicago-Downtown

Depart from your stay 🏨

12 - 15 min

Directions

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

8:00 AM - 11:00 AM

•

Free

10 - 15 min

Directions

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

11:30 AM - 1:30 PM

•

Free

8 - 11 min

Directions

2:00 PM - 3:30 PM

•

$51

7 - 10 min

Directions

7:00 PM - 8:30 PM

•

$51

Day 8Aquatic Wonders and Classic Diners

$270

$ 15

Homewood Suites by Hilton Chicago-Downtown

Depart from your stay 🏨

15 - 18 min

Directions

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

8:00 AM - 11:00 AM

•

$150

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.

1:00 PM - 2:30 PM

•

$54

8 - 11 min

Directions

7:00 PM - 8:30 PM

•

$66

Budget breakdown: $2081 In total

Activities & Food:$1931

Transport:$150