Chicago City Break • View Itinerary
Home Wish List Enquire Phone
Chicago Bean, Millennium Park
Chicago at dusk
Shedd Aquarium, Chicago, USA
Water Tower, Chicago, USA
The Magnificent Mile Chicago America
Navy Pier at night, Chicago, USA

Chicago City Break

4 day City Break – from £379

With flights from £1029

This sparkling city boasts everything from world-class museums and staggering architecture to rockin’ festivals and an excellent array of dining options.

Highlights:
  • Enjoy luxurious shopping along Chicago’s famed Magnificent Mile
  • Immerse yourself in the soulful rhythms of Chicago’s vibrant jazz and blues scene
  • Experience breathtaking heights at the Willis Tower
  • Delve into the rich history and diverse culture of Chicago

Your Itinerary

Expand All

You can customise this itinerary by adding extra nights or experiences. Just let us know what you would like to do.

Chicago at dusk

Day 1 – Welcome to Chicago

Welcome to Chicago! Make your way to your chosen hotel, where you can relax after your…

Welcome to Chicago! Make your way to your chosen hotel, where you can relax after your flight, or drop off your bags and head out into the energetic streets of this incredible city.

    Choice of Chicago Hotel

Chicago at dusk
Chicago Bean, Millennium Park

Day 2 to 3 – CityPASS & Free Time

Explore the city with the Chicago CityPASS. With this convenient pass, you’ll have access to the…

Explore the city with the Chicago CityPASS. With this convenient pass, you’ll have access to the city’s most iconic attractions, including the Shedd Aquarium, Skydeck Chicago, and The Field Museum. Dive into the underwater wonders of the Shedd Aquarium, where you’ll encounter a dazzling array of marine life. Then, ascend to the thrilling heights of Skydeck Chicago, where you can step out onto the glass-floored observation deck for panoramic views of the city skyline. Finally, immerse yourself in history and culture at The Field Museum, home to an impressive collection of artifacts and exhibits. With the Chicago CityPASS, you’ll enjoy a wonderful Chicago experience while saving time and money on admission to these must-see attractions.

    Choice of Chicago Hotel

Chicago Bean, Millennium Park
Navy Pier at night, Chicago, USA

Day 4 – Farewell from Chicago

Make your way to the airport for your flight home or on to your next destination.

Make your way to the airport for your flight home or on to your next destination.

Navy Pier at night, Chicago, USA

Your Itinerary

You can customise this itinerary by adding extra nights or experiences. Just let us know what you would like to do.

Day 1

|

Welcome to Chicago

Welcome to Chicago! Make your way to your chosen hotel, where you can relax after your flight, or drop off your bags and head out into the energetic streets of this incredible city.

    Choice of Chicago Hotel

Chicago at dusk

Day 2 to 3

|

CityPASS & Free Time

Explore the city with the Chicago CityPASS. With this convenient pass, you’ll have access to the city’s most iconic attractions, including the Shedd Aquarium, Skydeck Chicago, and The Field Museum. Dive into the underwater wonders of the Shedd Aquarium, where you’ll encounter a dazzling array of marine life. Then, ascend to the thrilling heights of Skydeck Chicago, where you can step out onto the glass-floored observation deck for panoramic views of the city skyline. Finally, immerse yourself in history and culture at The Field Museum, home to an impressive collection of artifacts and exhibits. With the Chicago CityPASS, you’ll enjoy a wonderful Chicago experience while saving time and money on admission to these must-see attractions.

    Choice of Chicago Hotel

Chicago Bean, Millennium Park

Day 4

|

Farewell from Chicago

Make your way to the airport for your flight home or on to your next destination.

Navy Pier at night, Chicago, USA

This City Break Includes

3 nights hotel accommodation
Chicago CityPASS

Flights & More

With FREEDOM, you can book your Chicago City Break city break and flights together, as an ATOL protected package. Our Travel Experts can find the best priced Economy, Premium or Business Class flights for you.

Next Step

Please get in touch with our America Experts to start planning your holiday. You’ll have a single point of contact from your first enquiry through booking.

Chicago City Break

4 day City Break – from £379

With flights from £1029