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Big Apple to the Windy City
Explore these two iconic cities connected by an Amtrak overnight train. You can of course fly if you wish, but we think the train is fun and gives you a chance to enjoy some of the very pretty countryside.
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
Your holiday starts with a flight to New York: on arrival you will be met...
Days 1-3
New York City
Your holiday starts with a flight to New York: on arrival you will be met and transferred to the hotel of your choice, where you will stay for three nights (more if you wish). Among our favourites are the Mark, the Pierre and a little less expensive – the Soho Grand or the Hilton Garden Inn. New York City, also known as The Big Apple, is a city of contrasts, where towering skyscrapers stand alongside vibrant neighbourhoods and world-class museums rub shoulders with street art and authentic ethnic cuisine. New York is a city that has something to offer everyone, from history buffs to fashionistas, from foodies to theatre-goers. We have included a tour pass which will give you discounted access to 4 of New York’s best attractions.
3 nights New York City
Day 4
New York City to Amtrak train
There are several train routes to get to Chicago. We have included the Lake Shore...
Day 4
New York City
to Amtrak train
There are several train routes to get to Chicago. We have included the Lake Shore Limited train as there are no changes and it is the shortest route at 19 ½ hours. Its disadvantage is that much of the journey is at night: it departs at 15:40 arriving in Chicago the following day at 10:12.
Alternatives include changing in Pittsburgh or Washington DC, these trains leave at around 11:00 arriving the following day at 08:45. 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 the Finger Lakes region 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-day attraction pass which will include such things 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.
