6 Days in Chicago: A Journey of Art, Adventure, and Delicious Eats!

Lissette Vasquez

8 Dec 2023

Experience the vibrant city of Chicago in 6 action-packed days! Discover iconic landmarks, immerse yourself in art and culture, and savor mouthwatering cuisine. From Millennium Park to Navy Pier, this itinerary will take you on an unforgettable adventure in the Windy City.

Trip to Chicago

Tours & Activities

Viator Tours

Day 1Fountain Delights and Artistic Wonders

$847

$ 70

Holiday Inn Express Chicago - Magnificent Mile, an IHG Hotel

Depart from your stay 🏨

7 - 9 min

Directions

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

8:00 AM - 9:00 AM

•

Free

3 - 4 min

Directions

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

9:30 AM - 12:30 PM

•

$224

8 - 11 min

Directions

1:00 PM - 2:30 PM

•

$252

5 - 8 min

Directions

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

2:30 PM - 4:30 PM

•

Free

12 - 15 min

Directions

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

5:00 PM - 7:00 PM

•

Free

6 - 9 min

Directions

7:30 PM - 9:00 PM

•

$196

34 - 41 min

Directions

Lions, tigers, dolphins & more frolic in natural indoor & outdoor settings at this wildlife park.

No time set

•

$175

Day 2Sky-high Thrills and Park Serenity

$1217

$ 105

Holiday Inn Express Chicago - Magnificent Mile, an IHG Hotel

Depart from your stay 🏨

8 - 12 min

Directions

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

8:00 AM - 9:00 AM

•

Free

12 - 15 min

Directions

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

9:30 AM - 11:30 AM

•

$219

1 - 2 min

Directions

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

12:00 PM - 1:30 PM

•

$219

17 - 21 min

Directions

2:00 PM - 3:30 PM

•

$196

9 - 14 min

Directions

Suburban recreational area with soccer & baseball fields, tennis courts & playgrounds, plus a beach.

3:30 PM - 5:30 PM

•

Free

18 - 22 min

Directions

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

6:00 PM - 7:30 PM

•

$219

4 - 5 min

Directions

8:00 PM - 9:30 PM

•

$189

9 - 11 min

Directions

Wide ice-skating track snaking around a rock-climbing facility in a park overlooked by skyscrapers.

No time set

•

Free

12 - 15 min

Directions

No time set

•

$175

Day 3Family Fun and Baseball Excitement

$1476

$ 53

Holiday Inn Express Chicago - Magnificent Mile, an IHG Hotel

Depart from your stay 🏨

12 - 15 min

Directions

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

8:00 AM - 10:00 AM

•

$131

5 - 8 min

Directions

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

10:30 AM - 12:30 PM

•

Free

15 - 18 min

Directions

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

1:00 PM - 2:30 PM

•

$224

6 - 9 min

Directions

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

2:30 PM - 5:30 PM

•

$924

11 - 16 min

Directions

7:00 PM - 8:30 PM

•

$196

Day 4Reflections in the Bean and Museum Marvels

$961

$ 53

Holiday Inn Express Chicago - Magnificent Mile, an IHG Hotel

Depart from your stay 🏨

9 - 11 min

Directions

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

8:00 AM - 9:00 AM

•

Free

14 - 17 min

Directions

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

9:30 AM - 1:30 PM

•

$263

16 - 20 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

•

$203

5 - 8 min

Directions

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

3:30 PM - 5:30 PM

•

Free

14 - 21 min

Directions

Downtown museum showcasing post-World War II paintings, sculptures, photos, videos & performances.

6:00 PM - 7:30 PM

•

$131

4 - 5 min

Directions

8:00 PM - 9:30 PM

•

$189

12 - 18 min

Directions

Beloved 1924 addition to the city skyline, whose clock tower stands 425 ft above street level.

No time set

•

Free

10 - 15 min

Directions

Interactive exhibits, artifacts & memorabilia help tell the story of the city's rich sports history.

No time set

•

$175

Day 5Cultural Treasures and Scenic Beauty

$385

$ 105

Holiday Inn Express Chicago - Magnificent Mile, an IHG Hotel

Depart from your stay 🏨

6 - 8 min

Directions

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

8:00 AM - 9:00 AM

•

Free

7 - 9 min

Directions

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

9:30 AM - 12:30 PM

•

Free

14 - 17 min

Directions

1:00 PM - 2:30 PM

•

$203

7 - 9 min

Directions

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

2:30 PM - 4:30 PM

•

Free

13 - 16 min

Directions

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

5:00 PM - 6:00 PM

•

Free

12 - 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

•

$182

Day 6Aquatic Wonders and Historic Landmarks

$1203

$ 35

Holiday Inn Express Chicago - Magnificent Mile, an IHG Hotel

Depart from your stay 🏨

14 - 17 min

Directions

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

8:00 AM - 11:00 AM

•

$350

5 - 8 min

Directions

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

11:30 AM - 2:30 PM

•

$219

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

•

$182

9 - 14 min

Directions