A Week in Chicago: Exploring the Windy City's Best

Mohammed Ali Fallah

1 Oct 2023

Join me on a thrilling 7-day adventure in Chicago, where we'll discover the city's iconic landmarks, indulge in delicious cuisine, and immerse ourselves in its vibrant culture.

Trip to Chicago

Tours & Activities

Viator Tours

Day 1

$141

$ 15

HI Chicago Hostel

Depart from your stay 🏨

12 - 15 min

Directions

Laid-back lodging offering casual dorms & private rooms, plus complimentary breakfast & tours.

7:30 AM - 7:30 AM

•

Free

7 - 10 min

Directions

7:30 AM - 8:30 AM

•

$16

12 - 15 min

Directions

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

9:00 AM - 10:30 AM

•

$63

6 - 9 min

Directions

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

11:00 AM - 1:00 PM

•

Free

7 - 10 min

Directions

1:30 PM - 3:00 PM

•

$36

12 - 17 min

Directions

Thousands of exotic plants in an 1890 glass structure, plus outdoor gardens & fountains.

3:00 PM - 4:00 PM

•

Free

7 - 10 min

Directions

Oz-themed playground/park with statues of the Tin Man, Scarecrow, Cowardly Lion & Dorothy.

4:30 PM - 5:30 PM

•

Free

7:00 PM - 8:30 PM

•

$26

Laid-back lodging offering casual dorms & private rooms, plus complimentary breakfast & tours.

7:30 AM - 7:30 AM

•

Free

Day 2

$142

$ 15

HI Chicago Hostel

Depart from your stay 🏨

12 - 15 min

Directions

Laid-back lodging offering casual dorms & private rooms, plus complimentary breakfast & tours.

7:30 AM - 7:30 AM

•

Free

8 - 12 min

Directions

7:30 AM - 8:30 AM

•

$30

11 - 16 min

Directions

Photos, artifacts, newsreels & dioramas bring to life historical events, architecture & culture.

9:00 AM - 11:00 AM

•

$50

12 - 15 min

Directions

11:30 AM - 1:30 PM

•

Free

6 - 9 min

Directions

House of Blues Restaurant & Bar will temporarily close for service operations until further notice. The safety of our guests, staff, and extended community has always been our highest priority; and these decisions are never made lightly...

2:00 PM - 3:30 PM

•

$24

5 - 8 min

Directions

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

3:30 PM - 4:30 PM

•

Free

7:00 PM - 8:30 PM

•

$38

Laid-back lodging offering casual dorms & private rooms, plus complimentary breakfast & tours.

7:30 AM - 7:30 AM

•

Free

Day 3

$211

$ 15

HI Chicago Hostel

Depart from your stay 🏨

6 - 8 min

Directions

Laid-back lodging offering casual dorms & private rooms, plus complimentary breakfast & tours.

7:30 AM - 7:30 AM

•

Free

5 - 8 min

Directions

7:30 AM - 8:30 AM

•

$14

7 - 9 min

Directions

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

9:00 AM - 10:00 AM

•

Free

11 - 14 min

Directions

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

10:30 AM - 12:30 PM

•

$63

13 - 20 min

Directions

1:00 PM - 2:30 PM

•

$24

4 - 6 min

Directions

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

2:30 PM - 5:30 PM

•

$63

Flat Top Stir-Fry Grill is a create-your-own stir-fry restaurant featuring fresh ingredients, house made sauces for a fun, fresh and interactive dining experience.

7:00 PM - 8:30 PM

•

$48

Laid-back lodging offering casual dorms & private rooms, plus complimentary breakfast & tours.

7:30 AM - 7:30 AM

•

Free

Day 4

$149

$ 10

HI Chicago Hostel

Depart from your stay 🏨

7 - 9 min

Directions

Laid-back lodging offering casual dorms & private rooms, plus complimentary breakfast & tours.

7:30 AM - 7:30 AM

•

Free

7 - 10 min

Directions

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

•

$24

4 - 5 min

Directions

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

9:00 AM - 10:30 AM

•

$63

5 - 8 min

Directions

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

11:00 AM - 12:00 PM

•

Free

4 - 5 min

Directions

12:30 PM - 2:00 PM

•

$36

12 - 17 min

Directions

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

2:00 PM - 4:00 PM

•

Free

7 - 10 min

Directions

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

4:30 PM - 6:30 PM

•

Free

Visit Buddy Guy's Legends to experience the finest blues seven nights a week, enjoy southern Cajun soul food, and behold a major archive of blues.

7:00 PM - 8:30 PM

•

$26

Laid-back lodging offering casual dorms & private rooms, plus complimentary breakfast & tours.

7:30 AM - 7:30 AM

•

Free

Day 5

$258

$ 15

HI Chicago Hostel

Depart from your stay 🏨

7 - 9 min

Directions

Laid-back lodging offering casual dorms & private rooms, plus complimentary breakfast & tours.

7:30 AM - 7:30 AM

•

Free

12 - 17 min

Directions

7:30 AM - 8:30 AM

•

$20

5 - 6 min

Directions

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

9:00 AM - 12:00 PM

•

$100

8 - 10 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

3 - 4 min

Directions

2:00 PM - 3:30 PM

•

$48

3 - 4 min

Directions

Immersive rooms with optical illusions & holograms designed to deceive the eye, popular for photos.

3:30 PM - 5:00 PM

•

$50

7:00 PM - 8:30 PM

•

$40

Laid-back lodging offering casual dorms & private rooms, plus complimentary breakfast & tours.

7:30 AM - 7:30 AM

•

Free

Day 6

$173

$ 10

HI Chicago Hostel

Depart from your stay 🏨

10 - 15 min

Directions

Laid-back lodging offering casual dorms & private rooms, plus complimentary breakfast & tours.

7:30 AM - 7:30 AM

•

Free

10 - 15 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

7:30 AM - 8:30 AM

•

$22

8 - 10 min

Directions

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

9:00 AM - 12:00 PM

•

$63

7 - 10 min

Directions

Famous Chicago-style deep dish pizza right in your neighborhood. Visit us for a family-friendly atmosphere and delicious food or order your meal online for pickup or delivery.

12:30 PM - 2:00 PM

•

$40

3 - 4 min

Directions

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

2:00 PM - 4:00 PM

•

Free

5 - 8 min

Directions

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

4:30 PM - 5:30 PM

•

Free

7:00 PM - 8:30 PM

•

$48

Laid-back lodging offering casual dorms & private rooms, plus complimentary breakfast & tours.

7:30 AM - 7:30 AM

•

Free

Day 7

$136

$ 25

HI Chicago Hostel

Depart from your stay 🏨

22 - 27 min

Directions

Laid-back lodging offering casual dorms & private rooms, plus complimentary breakfast & tours.

7:30 AM - 7:30 AM

•

Free

7 - 9 min

Directions

7:30 AM - 8:30 AM

•

$18

13 - 16 min

Directions

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

9:00 AM - 1:00 PM

•

$50

14 - 17 min

Directions

Famous Chicago-style deep dish pizza right in your neighborhood. Visit us for a family-friendly atmosphere and delicious food or order your meal online for pickup or delivery.

1:30 PM - 3:00 PM

•

$34

7:00 PM - 8:30 PM

•

$34

Laid-back lodging offering casual dorms & private rooms, plus complimentary breakfast & tours.

7:30 AM - 7:30 AM

•

Free

Budget breakdown: $1314 In total

Activities & Food:$1209

Transport:$105