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Two Cities by Rail
Get ready to embark on an unforgettable journey that fuses the rich heritage of Boston with the vibrant energy of Chicago. This dynamic doubleheader lets you experience the best of both worlds: the quaint cobblestone streets of Beantown alongside the soaring skyscrapers of the Windy City.
Boston will immerse you in the American Revolution’s rich tapestry. Walk the Freedom Trail, a red-brick path leading past historical landmarks like the Faneuil Hall marketplace and the venerated Bunker Hill Monument. Don’t forget to cheer on the home team at a Fenway Park baseball game, a quintessential Boston experience.
Chicago, the “City of Big Shoulders,” offers a completely different perspective. Immerse yourself in breath taking architecture, from the neoclassical grandeur of the Art Institute of Chicago to the iconic bean-shaped sculpture in Millennium Park. Savour the city’s deep-dish pizza and indulge in world-class jazz music in legendary clubs.
This itinerary is flexible and can be tailor-made to suit you; if you want to add extra days in one area, extend the holiday or maybe change the direction of travel. Talk to one of our experts about how to make this holiday the perfect one for you.
Ms Young"Seamless Holiday"
We used Frontier Travel to book our honeymoon. We were given all the information we needed and everything ran seamlessly. We had a fantastic time, the hotels and lodges were perfect. Thank you for organising such a brilliant trip!
Itinerary (7 Nights)
Here’s a day-by-day guide to your itinerary. Feel free to ask us to add other days or ideas and excursions by contacting us directly, so we can give you the best price.
Days 1-3
Fly into Boston where you will be met and transferred to the hotel of your...
Days 1-3
Boston
Fly into Boston where you will be met and transferred to the hotel of your choice. Among our favourites are the Onyx, the Colonnade Hotel and the Westin Copley Plaza. Boston, a city steeped in history and culture, is a vibrant hub of academic excellence, technological innovation and culinary delights. From exploring its rich Revolutionary War heritage to indulging in its diverse culinary scene, Boston offers an unforgettable experience and we have included a discounted five-attraction pass which will include such things as a 1-day Hop-On Hop-Off Big Bus Tour, a sunset cruise and the Boston Museum of Fine Arts.
3 nights Boston
Day 4
Boston to Amtrak train
The Lake Shore Limited train departs from Boston South Station at 12:50, arriving in Chicago...
Day 4
Boston
to Amtrak train
The Lake Shore Limited train departs from Boston South Station at 12:50, arriving in Chicago the following day at 10:12. Accommodation on the train is either a regular seat or a choice of private rooms which can either be a compact roomette with an upper and lower bunk or a bedroom which is twice the size and includes a private lavatory, shower and basin. Both fares include all meals and a First Class attendant on board. The route will take you through Worcester and Springfield in Massachusetts to Albany, along the Mohawk River past the Erie Canal, through Buffalo along the south shore of Lake Erie, one of the prettiest in the US, to Cleveland and on to South Bend, the south shore of Lake Michigan and into Chicago.
1 night Amtrak, Lake Shore Limited train
Days 5-7
Amtrak train to Chicago
From the grandeur of Grant Park’s Buckingham Fountain to iconic museums and skyscrapers, see for...
Days 5-7
Amtrak train
to Chicago
From the grandeur of Grant Park’s Buckingham Fountain to iconic museums and skyscrapers, see for yourself why Chicago was once dubbed “Paris on the Prairie.” Engage in retail therapy on the Magnificent Mile or root for the home team, be it the Sox or the Cubbies at famed Wrigley Field. Make your way to the hotel of your choice: we would recommend the Drake, the Hyatt Regency or the Warwick Allerton among the hundreds there are to choose from. We have included a discounted three attraction pass which will include such opportunities as a 1-day Hop-On Hop-Off Big Bus Tour, the Skydeck at Willis Tower or a river cruise.
3 nights Chicago
Day 8
Chicago
A private car will collect you from your hotel and take you to the airport...
Day 8
Chicago
A private car will collect you from your hotel and take you to the airport for your homeward flight.
