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

Adelina Decrescenzo

2 Oct 2023

Embark on a 6-day adventure in Chicago, IL, and experience the city's vibrant food scene and iconic landmarks. From indulging in delicious pancakes to marveling at breathtaking views from the Skydeck, this itinerary has it all!

Trip to Chicago

Tours & Activities

Viator Tours

Day 1

$407

$ 25

The Westin Michigan Avenue Chicago

Depart from your stay 🏨

13 - 16 min

Directions

Polished lodging with refined rooms & suites, plus a steakhouse, lake views & 34 meeting rooms.

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

•

$40

8 - 11 min

Directions

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

9:00 AM - 10:30 AM

•

$156

5 - 8 min

Directions

1:00 PM - 2:30 PM

•

$90

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

•

$120

Polished lodging with refined rooms & suites, plus a steakhouse, lake views & 34 meeting rooms.

7:30 AM - 7:30 AM

•

Free

Day 2

$387

$ 13

The Westin Michigan Avenue Chicago

Depart from your stay 🏨

6 - 8 min

Directions

Polished lodging with refined rooms & suites, plus a steakhouse, lake views & 34 meeting rooms.

7:30 AM - 7:30 AM

•

Free

9 - 14 min

Directions

7:30 AM - 8:30 AM

•

$75

11 - 16 min

Directions

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

9:00 AM - 11:00 AM

•

$156

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

•

$60

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

7:00 PM - 8:30 PM

•

$95

Polished lodging with refined rooms & suites, plus a steakhouse, lake views & 34 meeting rooms.

7:30 AM - 7:30 AM

•

Free

Day 3

$300

$ 13

The Westin Michigan Avenue Chicago

Depart from your stay 🏨

8 - 10 min

Directions

Polished lodging with refined rooms & suites, plus a steakhouse, lake views & 34 meeting rooms.

7:30 AM - 7:30 AM

•

Free

8 - 11 min

Directions

7:00 PM - 8:30 PM

•

$120

6 - 9 min

Directions

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

9:00 AM - 11:00 AM

•

Free

7 - 10 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

•

$60

7:00 PM - 8:30 PM

•

$120

Polished lodging with refined rooms & suites, plus a steakhouse, lake views & 34 meeting rooms.

7:30 AM - 7:30 AM

•

Free

Day 4

$372

The Westin Michigan Avenue Chicago

Depart from your stay 🏨

6 - 9 min

Directions

Polished lodging with refined rooms & suites, plus a steakhouse, lake views & 34 meeting rooms.

7:30 AM - 7:30 AM

•

Free

7 - 10 min

Directions

7:30 AM - 8:30 AM

•

$60

4 - 5 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

•

$156

8 - 11 min

Directions

1:00 PM - 2:30 PM

•

$90

7:00 PM - 8:30 PM

•

$65

Polished lodging with refined rooms & suites, plus a steakhouse, lake views & 34 meeting rooms.

7:30 AM - 7:30 AM

•

Free

Day 5

$427

$ 25

The Westin Michigan Avenue Chicago

Depart from your stay 🏨

12 - 15 min

Directions

Polished lodging with refined rooms & suites, plus a steakhouse, lake views & 34 meeting rooms.

7:30 AM - 7:30 AM

•

Free

7 - 10 min

Directions

7:30 AM - 8:30 AM

•

$50

10 - 15 min

Directions

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

9:00 AM - 11:00 AM

•

$156

11 - 16 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

•

$120

7:00 PM - 8:30 PM

•

$100

Polished lodging with refined rooms & suites, plus a steakhouse, lake views & 34 meeting rooms.

7:30 AM - 7:30 AM

•

Free

Day 6

$275

$ 25

The Westin Michigan Avenue Chicago

Depart from your stay 🏨

8 - 10 min

Directions

Polished lodging with refined rooms & suites, plus a steakhouse, lake views & 34 meeting rooms.

7:30 AM - 7:30 AM

•

Free

5 - 8 min

Directions

7:30 AM - 8:30 AM

•

$55

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

4 - 5 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

•

$100

7:00 PM - 8:30 PM

•

$120

Polished lodging with refined rooms & suites, plus a steakhouse, lake views & 34 meeting rooms.

7:30 AM - 7:30 AM

•

Free

Budget breakdown: $2265 In total

Activities & Food:$2165

Transport:$100