Sure, here’s your itinerary for the Chicago trip.

Day 1:

3:00 PM - Land in Chicago. Take transportation to hotel and check-in.

6:00 PM - Visit the John Hancock Center, enjoy the panoramic views of the Windy City.

8:00 PM - Dinner at Pequod’s Pizza, famous for its deep-dish pizza.

Day 2:

9:00 AM - Breakfast at your hotel.

10:30 AM - Begin your day exploring the city’s architecture with the Chicago Architecture Foundation River Cruise on the Chicago River.

1:00 PM - Lunch at a local cafe.

2:30 PM - Visit the Chicago Riverwalk, relax and enjoy the views or engage in recreational activities.

7:00 PM - Dinner at Gibsons Bar & Steakhouse, one of the most famous steakhouses in Chicago.

Day 3:

9:00 AM - Breakfast at your hotel.

10:30 AM - Visit the Cloud Gate also known as “The Bean” at the Millennium Park.

1:00 PM - Lunch at a local eatery.

2:30 PM - Free time for shopping or explore other attractions in Chicago.

7:00 PM - Dinner at a restaurant of your choice.

Day 4:

9:00 AM - Breakfast at your hotel.

10:00 AM - Check-out from the hotel and take transportation to the airport.

12:00 PM - Depart from Chicago.

Of course, this is just a suggested itinerary and Chicago has a lot more to offer! You can modify this itinerary according to your preferences and the pace at which you would like to tour. Enjoy your trip!