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

Horys Jimenez

17 Oct 2023

Embark on a 6-day adventure in Chicago, IL, and indulge in mouthwatering meals at iconic restaurants while visiting top attractions like Skydeck Chicago, Millennium Park, and Navy Pier.

Trip to Chicago

Tours & Activities

Viator Tours

Day 1

$116

$ 8

HI Chicago Hostel

Depart from your stay 🏨

10 - 12 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

•

7 - 9 min

Directions

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

9:00 AM - 10:30 AM

•

$31

3 - 4 min

Directions

11:00 AM - 11:30 AM

•

$45

5 - 8 min

Directions

1:00 PM - 2:30 PM

•

$18

7:00 PM - 8:30 PM

•

$13

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

7:30 AM - 7:30 AM

•

Free

Day 2

$39

$ 5

HI Chicago Hostel

Depart from your stay 🏨

8 - 10 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

•

$15

6 - 9 min

Directions

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

9:00 AM - 11:00 AM

•

Free

3 - 4 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.

1:00 PM - 2:30 PM

•

$12

By Millenium Park at Lake and Michigan, Downtown Chicago restaurant Roti Modern Mediterranean offers a menu of deliciously fresh salads, bowls, & pitas

1:00 PM - 2:30 PM

•

$12

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

7:30 AM - 7:30 AM

•

Free

Day 3

$43

HI Chicago Hostel

Depart from your stay 🏨

11 - 16 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

•

6 - 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

8 - 12 min

Directions

By Millenium Park at Lake and Michigan, Downtown Chicago restaurant Roti Modern Mediterranean offers a menu of deliciously fresh salads, bowls, & pitas

1:00 PM - 2:30 PM

•

$12

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

•

$24

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

7:30 AM - 7:30 AM

•

Free

Day 4

$75

HI Chicago Hostel

Depart from your stay 🏨

4 - 6 min

Directions

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

7:30 AM - 7:30 AM

•

Free

4 - 6 min

Directions

7:30 AM - 8:30 AM

•

$12

6 - 9 min

Directions

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

9:00 AM - 12:00 PM

•

$31

5 - 8 min

Directions

1:00 PM - 2:30 PM

•

$18

7:00 PM - 8:30 PM

•

$13

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

7:30 AM - 7:30 AM

•

Free

Day 5

$86

$ 5

HI Chicago Hostel

Depart from your stay 🏨

10 - 12 min

Directions

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

7:30 AM - 7:30 AM

•

Free

9 - 14 min

Directions

7:30 AM - 8:30 AM

•

$10

11 - 16 min

Directions

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

9:00 AM - 11:00 AM

•

$31

4 - 6 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.

1:00 PM - 2:30 PM

•

$24

Quick casual restaurant featuring Original Italian Beef, Pizza, Burgers, Hot Dogs, Sandwiches and Salads

7:00 PM - 8:30 PM

•

$20

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

7:30 AM - 7:30 AM

•

Free

Day 6

$105

$ 3

HI Chicago Hostel

Depart from your stay 🏨

9 - 11 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

7:30 AM - 8:30 AM

•

$11

15 - 22 min

Directions

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

9:00 AM - 12:00 PM

•

$50

10 - 15 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

•

$20

7:00 PM - 8:30 PM

•

$24

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

7:30 AM - 7:30 AM

•

Free

Budget breakdown: $482 In total

Activities & Food:$462

Transport:$20