Summary
Discover the very best of the USA with our Boston to Chicago multi-centre holiday package. Begin with a 3-night stay in Boston, the historic capital of Massachusetts, where rich American heritage blends seamlessly with a vibrant modern culture. From here, travel by rail to New York, immersing yourself in the energy and excitement of the city that never sleeps.
After experiencing the highlights of the East Coast, continue your journey to Chicago, a city famed for its striking architecture, cultural attractions, and lively waterfront. Often compared to the Champs-Élysées, the Magnificent Mile is a grand boulevard lined with upscale shops, museums, and stylish restaurants. Stroll along to the historic Navy Pier and take a ride on its iconic 148-foot Ferris wheel for spectacular views of the city skyline and Lake Michigan. Explore iconic cities, diverse cultures, and unforgettable experiences with our Boston to Chicago holiday packages.
Dates and Prices
November 2026
From £1,349
December 2026
From £1,349
January 2027
From £1,149
February 2027
From £1,199
March 2027
From £1,299
April 2027
From £1,599
May 2027
From £1,849
June 2027
From £1,949
July 2027
From £1,899
August 2027
From £1,849
November 2026
From £1,499
December 2026
From £1,499
January 2027
From £1,249
February 2027
From £1,299
March 2027
From £1,449
April 2027
From £1,749
May 2027
From £1,999
June 2027
From £1,999
July 2027
From £2,049
August 2027
From £1,999
November 2026
From £1,549
December 2026
From £1,549
January 2027
From £1,299
February 2027
From £1,349
March 2027
From £1,449
April 2027
From £1,749
May 2027
From £1,999
June 2027
From £1,999
July 2027
From £2,049
August 2027
From £2,149
Please select number of passengers
Price per person
$458
Total Price
$7,458
Plan Your Dream Trip
Gallery
Itinerary
Day 1
Fly from UK airport to Boston
- Depart from your chosen UK airport on your international flight to Boston. On arrival, complete immigration and transfer to your hotel. Spend the rest of the day at leisure, perhaps taking a gentle walk around the historic downtown area. Overnight stay in Boston.
Day 2
- Enjoy a full day to explore Boston. Walk the famous Freedom Trail, visit historic sites such as Faneuil Hall and Quincy Market, or explore Harvard University and MIT across the river in Cambridge. Overnight stay in Boston.
Day 3
Stay in Boston
- Spend the day at leisure discovering more of Boston’s charm. Options include a harbour cruise, exploring Boston Common and Public Garden, or visiting the New England Aquarium. Overnight stay in Boston.
Day 4
Take train from Boston to New York & Stay
- Check out from your hotel and transfer to the station for your scenic Amtrak train journey from Boston to New York. On arrival, transfer to your hotel and enjoy your first evening in the city that never sleeps. Overnight stay in New York.
Day 5
Stay in New York
- Explore New York at your own pace. Highlights include Times Square, Central Park, Fifth Avenue, Wall Street, and the Statue of Liberty. Optional museum visits include the Metropolitan Museum of Art or MoMA. Overnight stay in New York.
Day 6
Stay in New York
- Another day to enjoy New York’s diverse neighbourhoods. Visit Brooklyn, walk across the Brooklyn Bridge, explore Chinatown and Little Italy, or enjoy a Broadway show in the evening. Overnight stay in New York.
Day 7
Fly from New York to Chicago & Stay
- Check out from your hotel and transfer to the airport for your internal flight from New York to Chicago. On arrival, transfer to your hotel and relax or enjoy an evening stroll along the Magnificent Mile. Overnight stay in Chicago.
Day 8
Stay in Chicago
- Discover Chicago’s famous attractions, including Millennium Park and Cloud Gate (The Bean), Navy Pier, and the Art Institute of Chicago. Enjoy shopping and dining along the Magnificent Mile. Overnight stay in Chicago.
Day 9
Stay in Chicago
- Spend your final full day exploring more of Chicago. Optional activities include an architecture river cruise, visiting Willis Tower Skydeck, or relaxing along the shores of Lake Michigan. Overnight stay in Chicago.
Day 10
Fly from Chicago to UK airport
- Check out from your hotel and transfer to the airport for your return flight from Chicago to the UK, bringing your memorable multi-centre USA holiday to an end.
At a Glance
- Your Holiday At a Glance
- 3 Nights Boston
- 3 nightsNew York
- 3 Nights Chicago
- Amtrak train journey from Boston to New York
- Internal flights from New York to Chicago
- Prices are based on two adults sharing
- City Tax not included: payable directly on site
- Offer Subject to Popular Holidays Terms & Conditions
