Chicago Adventure: 6 Days of Exploring the Windy City

Carolina Aguilar

17 Oct 2023

Embark on a thrilling 6-day journey through the vibrant city of Chicago. Discover iconic landmarks, indulge in delicious cuisine, and immerse yourself in the rich culture of the Windy City.

Trip to Chicago

Tours & Activities

Viator Tours

Day 1

$329

$ 70

Aloft Chicago Mag Mile

Depart from your stay 🏨

7 - 9 min

Directions

Relaxed quarters, some with city views, in a refined hotel offering complimentary Wi-Fi & a pool.

7:30 AM - 7:30 AM

•

Free

8 - 11 min

Directions

We have been serving our delicious subs, soups and salads for over 50 Years! We will continue to do so along with a few new additions to the Fontano’s menu. ...

7:30 AM - 8:30 AM

•

$133

12 - 15 min

Directions

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

9:00 AM - 10:00 AM

•

Free

8 - 10 min

Directions

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

10:30 AM - 12:30 PM

•

Free

7:00 PM - 8:30 PM

•

$196

Relaxed quarters, some with city views, in a refined hotel offering complimentary Wi-Fi & a pool.

7:30 AM - 7:30 AM

•

Free

Day 2

$625

$ 35

Aloft Chicago Mag Mile

Depart from your stay 🏨

11 - 14 min

Directions

Relaxed quarters, some with city views, in a refined hotel offering complimentary Wi-Fi & a pool.

7:30 AM - 7:30 AM

•

Free

8 - 12 min

Directions

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

•

$161

8 - 10 min

Directions

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

9:00 AM - 11:00 AM

•

Free

4 - 5 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

•

$219

7:00 PM - 8:30 PM

•

$245

Relaxed quarters, some with city views, in a refined hotel offering complimentary Wi-Fi & a pool.

7:30 AM - 7:30 AM

•

Free

Day 3

$562

$ 18

Aloft Chicago Mag Mile

Depart from your stay 🏨

8 - 11 min

Directions

Relaxed quarters, some with city views, in a refined hotel offering complimentary Wi-Fi & a pool.

7:30 AM - 7:30 AM

•

Free

10 - 15 min

Directions

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

•

$147

10 - 12 min

Directions

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

9:00 AM - 11:00 AM

•

$219

6 - 9 min

Directions

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

11:30 AM - 1:30 PM

•

Free

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

•

$196

Relaxed quarters, some with city views, in a refined hotel offering complimentary Wi-Fi & a pool.

7:30 AM - 7:30 AM

•

Free

Day 4

$343

$ 18

Aloft Chicago Mag Mile

Depart from your stay 🏨

6 - 8 min

Directions

Relaxed quarters, some with city views, in a refined hotel offering complimentary Wi-Fi & a pool.

7:30 AM - 7:30 AM

•

Free

4 - 5 min

Directions

7:30 AM - 8:30 AM

•

$154

2 - 3 min

Directions

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

9:00 AM - 10:00 AM

•

Free

5 - 8 min

Directions

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

10:30 AM - 12:30 PM

•

Free

7:00 PM - 8:30 PM

•

$189

Relaxed quarters, some with city views, in a refined hotel offering complimentary Wi-Fi & a pool.

7:30 AM - 7:30 AM

•

Free

Day 5

$795

$ 35

Aloft Chicago Mag Mile

Depart from your stay 🏨

10 - 12 min

Directions

Relaxed quarters, some with city views, in a refined hotel offering complimentary Wi-Fi & a pool.

7:30 AM - 7:30 AM

•

Free

5 - 8 min

Directions

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

•

$175

1 - 2 min

Directions

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

9:00 AM - 10:30 AM

•

$219

8 - 11 min

Directions

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

11:00 AM - 1:00 PM

•

$219

7:00 PM - 8:30 PM

•

$182

Relaxed quarters, some with city views, in a refined hotel offering complimentary Wi-Fi & a pool.

7:30 AM - 7:30 AM

•

Free

Day 6

$797

$ 18

Aloft Chicago Mag Mile

Depart from your stay 🏨

13 - 20 min

Directions

Relaxed quarters, some with city views, in a refined hotel offering complimentary Wi-Fi & a pool.

7:30 AM - 7:30 AM

•

Free

2 - 3 min

Directions

7:30 AM - 8:30 AM

•

$126

10 - 15 min

Directions

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

9:00 AM - 11:00 AM

•

$263

4 - 5 min

Directions

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

11:30 AM - 2:30 PM

•

$219

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

•

$189

Relaxed quarters, some with city views, in a refined hotel offering complimentary Wi-Fi & a pool.

7:30 AM - 7:30 AM

•

Free

Budget breakdown: $3642 In total

Activities & Food:$3450

Transport:$193