Chicago Adventure: 5-Day Itinerary

Carlos “DR BEAT DJ” Cabrera

17 Oct 2023

Embark on an unforgettable journey through the vibrant city of Chicago. Explore 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

$94

$ 10

La Quinta Inn & Suites by Wyndham Chicago Downtown

Depart from your stay 🏨

28 - 34 min

Directions

La Quinta Inn & Suites by Wyndham Chicago Downtown

Straightforward rooms & suites in a laid-back lodging offering free breakfast & a fitness room.

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

•

$38

14 - 17 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

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

11:30 AM - 12:30 PM

•

Free

3 - 4 min

Directions

Landmark sign at the start of the fabled Route 66, which stretches from Chicago to Los Angeles.

1:00 PM - 1:30 PM

•

Free

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

•

$56

Straightforward rooms & suites in a laid-back lodging offering free breakfast & a fitness room.

7:30 AM - 7:30 AM

•

Free

Day 2

$116

La Quinta Inn & Suites by Wyndham Chicago Downtown

Depart from your stay 🏨

9 - 14 min

Directions

Straightforward rooms & suites in a laid-back lodging offering free breakfast & a fitness room.

7:30 AM - 7:30 AM

•

Free

3 - 4 min

Directions

7:30 AM - 8:30 AM

•

$46

4 - 6 min

Directions

Collection of artifacts, films & books on US military history, housed in an ornate 1912 building.

9:00 AM - 10:30 AM

•

Free

10 - 15 min

Directions

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

11:00 AM - 12:00 PM

•

Free

6 - 9 min

Directions

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

12:30 PM - 2:30 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

•

$70

Straightforward rooms & suites in a laid-back lodging offering free breakfast & a fitness room.

7:30 AM - 7:30 AM

•

Free

Day 3

$169

$ 5

La Quinta Inn & Suites by Wyndham Chicago Downtown

Depart from your stay 🏨

11 - 16 min

Directions

Straightforward rooms & suites in a laid-back lodging offering free breakfast & a fitness room.

7:30 AM - 7:30 AM

•

Free

2 - 3 min

Directions

7:30 AM - 8:30 AM

•

$42

8 - 11 min

Directions

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

9:00 AM - 11:00 AM

•

$75

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

7:00 PM - 8:30 PM

•

$52

Straightforward rooms & suites in a laid-back lodging offering free breakfast & a fitness room.

7:30 AM - 7:30 AM

•

Free

Day 4

$98

$ 5

La Quinta Inn & Suites by Wyndham Chicago Downtown

Depart from your stay 🏨

14 - 21 min

Directions

Straightforward rooms & suites in a laid-back lodging offering free breakfast & a fitness room.

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

•

$44

12 - 18 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

9 - 14 min

Directions

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

10:30 AM - 1:30 PM

•

Free

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

7:00 PM - 8:30 PM

•

$54

Straightforward rooms & suites in a laid-back lodging offering free breakfast & a fitness room.

7:30 AM - 7:30 AM

•

Free

Day 5

$165

$ 15

La Quinta Inn & Suites by Wyndham Chicago Downtown

Depart from your stay 🏨

12 - 15 min

Directions

Straightforward rooms & suites in a laid-back lodging offering free breakfast & a fitness room.

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

•

$50

9 - 11 min

Directions

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

9:00 AM - 11:00 AM

•

$63

12 - 18 min

Directions

18.5-mi. mixed-use trail along Lake Michigan, with multiple parks & city skyline views.

11:30 AM - 1:30 PM

•

Free

7:00 PM - 8:30 PM

•

$52

Straightforward rooms & suites in a laid-back lodging offering free breakfast & a fitness room.

7:30 AM - 7:30 AM

•

Free

Budget breakdown: $677 In total

Activities & Food:$642

Transport:$35