Chicago City Break

Holiday Highlights

Experience the energy of Chicago with an unforgettable city break filled with iconic attractions, world-class dining and stunning skyline views. Explore Millennium Park, Navy Pier and the Magnificent Mile, then discover deep-dish pizza, rooftop bars and vibrant neighbourhoods in one of America’s most exciting and stylish cities.

4 Nights Millennium Hotel Knickerbocker Chicago

  • Beautiful & Historic Chicago Hotel
  • One of the Best Downtown Locations – Close to Sightseeing, Restaurants & Shopping
  • Luxurious Guest Rooms & Amenities
  • Kid’s Menu’s & Maps to Kid Friendly Attractions
  • Concierge
4 Nights
More USA holiday
From £883 pp
Price Breakdown:
Holiday Cost: £883 per person
In Destination Cost: £68 per person
Holiday Code: #D102
Chicago City Break
From £883 pp

What's Included

Wide Range of Dates Available
Call Now for more Details

Inclusions:

  • Round Trip UK Flights
  • Accommodation
  • Private Transfers
  • ABTA Protection

If you would like to enquire about this city break to Chicago, contact us on 020 3542 8888 and quote Offer Code D102

Based on 2 Adults sharing, London departure, 8th March 2027, call for your perfect dates, we are always happy to help!
Core Holiday Price £849pp
In Destination Resort Fees approx £34pp (charged locally in USD)

Pricing

2026-2027
Bookable All Year Round
£883 pp
Example price based on 8th March 2027

About Chicago City Break

Experience one of America’s greatest city destinations with a trip to Chicago, a city famous for world-class attractions, iconic architecture and an outstanding food scene. Set on the shores of Lake Michigan, Chicago combines big-city energy with scenic waterfront views, creating the perfect destination for couples, families and city-break travellers alike.

Explore Iconic Chicago

Chicago is home to some of the USA’s most recognisable attractions. Visit Millennium Park and snap a photo beside Cloud Gate, better known as “The Bean.” Then head to Navy Pier for lakeside entertainment, restaurants and skyline views.

For breathtaking panoramas, visit Skydeck Chicago at Willis Tower or 360 CHICAGO at the John Hancock Center. Meanwhile, architecture lovers can enjoy famous river cruises showcasing the city’s incredible skyline and historic buildings.

Chicago is also a major cultural hub. The Art Institute of Chicago features world-famous masterpieces, while the Theatre District hosts Broadway productions, live music and comedy shows year-round.

Food, Drink & Neighbourhoods

Chicago’s food scene is one of the best in America. The city is famous for deep-dish pizza, classic steakhouses and award-winning restaurants. In addition, craft breweries, rooftop bars and neighbourhood food halls provide endless dining options.

Explore neighbourhoods such as River North, Wicker Park and the West Loop, each offering their own character, shopping and nightlife. From luxury boutiques along the Magnificent Mile to local bakeries and coffee shops, Chicago delivers something for every traveller.

Sports & Entertainment

Sports are central to Chicago’s identity. Catch a Chicago Cubs game at historic Wrigley Field or experience the electric atmosphere surrounding the Bulls, Bears and Blackhawks.

Throughout the year, the city also hosts festivals, concerts and lakefront events, ensuring there is always something happening.

Discover Wider Illinois

Beyond the city, Illinois offers scenic road trips, outdoor adventure and charming small towns. Travel historic Route 66 through classic Americana landscapes or follow the Great River Road alongside the Mississippi River.

Southern Illinois is home to Shawnee National Forest and the spectacular Garden of the Gods rock formations. Meanwhile, destinations such as Galena offer wineries, historic streets and relaxed countryside escapes.

From Chicago’s iconic skyline to Illinois’ scenic backroads, this destination combines culture, food, history and outdoor beauty into one unforgettable experience.

Call TravelPlanners on 020 3542 8888 and let’s get you there today!

4 Nights
More USA holiday
From £883 per person
Price Breakdown:
Holiday Cost: £883 per person
In Destination Cost: £68 per person
Holiday Code: #D102

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