4 Day Chicago Itinerary

A reunion adventure that will guide a group of college friends through the iconic landmarks of Chicago over 4 days, starting from February 10, 2050, until February 13, 2050. From city park explorations, and art excursions, to a scenic river architecture cruise, this itinerary ensures a memorable journey.

Day 1: Arrival and Exploration

Time Slot	Activities
Morning	Arrive in Chicago and check into your hotel. Drop off your luggage and freshen up.
Afternoon	Head to Millennium Park and explore the iconic Cloud Gate sculpture (The Bean). Stroll through the park and enjoy the scenery.
Evening	Have dinner at a local restaurant. Consider trying deep-dish pizza, a Chicago specialty.
Night	Relax at your hotel or explore the nightlife in the area.

Day 2: Cultural and Architectural Delights

Time Slot	Activities
Morning	Start your day with a visit to the Art Institute of Chicago. Explore the museum's vast collection of art, including works by famous artists like Grant Wood and Georges Seurat.
Afternoon	After lunch, take an architectural boat tour along the Chicago River. Learn about the city's famous buildings and skyline.
Evening	Enjoy dinner at a waterfront restaurant overlooking Lake Michigan.
Night	Take a stroll along the Navy Pier and enjoy the views of the city skyline lit up at night.

Day 3: Shopping and Sightseeing

Time Slot	Activities
Morning	Visit the Magnificent Mile, Chicago's premier shopping destination. Browse through the many shops and boutiques.
Afternoon	After shopping, visit the John Hancock Center and take the elevator to the 360 Chicago Observation Deck. Enjoy panoramic views of the city.
Evening	Have dinner at a restaurant in the area.
Night	If you're up for it, consider visiting a jazz club or comedy club for some evening entertainment.

Day 4: Farewell and Departure

Time Slot	Activities
Morning	Check out of your hotel and take a walk along Lake Michigan. Enjoy the morning breeze and take in the views.
Afternoon	Visit the Field Museum or the Shedd Aquarium, depending on your interests.
Evening	Have a farewell dinner at a restaurant of your choice.
Night	Depart from Chicago or spend one more night in the city, depending on your travel plans.

Budget and Expenses:

Hotel: $200-$400 per night (depending on the hotel)
Meals: $50-$100 per day (depending on the restaurant)
Activities: $50-$100 per day (depending on the attractions)

Essentials Checklist:

Comfortable walking shoes.
Weather-appropriate clothing (layers are recommended).
Camera or smartphone for photos.
Travel guide or map of Chicago.
Personal items (toiletries, medications, etc.).

This itinerary is designed to give you a taste of Chicago's culture, architecture, and cuisine in just four days. Adjustments can be made based on your interests and preferences. Enjoy your time in the Windy City!