Chicago, Niagara & New York Itinerary

Travel from Chicago to New York via Canada. Travel to Toronto, visit Niagara Falls and make a stopover in Montreal and Boston for a solid dose of history and culture.

    • 10
    • SSSA
    • Total price tool tip
      USD $2,197
      CAD $2,227
      AUD $2,313
      EUR €1,608
      GBP £1,383
      NZD $2,741
      ZAR R21,060
      CHF FR1,983
      *
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Niagara Falls, Canada

Times Square, USA

Downtown building, USA

Days 1-2 Chicago

Begin the adventure in the biggest and boldest city in the Midwest – Chicago. The third most populous city in the United States, and definitely one of the friendliest, Chicago is known for its vibrant urban culture, lakeside walking trails and some seriously stunning architecture.
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Days 3-4 Toronto/Niagara Falls

Cross the border into Canada and perhaps head up the giant CN tower for a look at this ultra-cool, ultra-clean capital – or see it from the ground on an optional bike tour. The next day, get a dose of one of North America’s most iconic marvels on a daytrip to the rampaging waters of Niagara Falls. If it’s not too cold, don a raincoat and head out on the waters for a Maid of the Mist boat tour.
ACCOM: Hotel - 2

Days 5-6 Montreal

Brush up on your French and discover a city that wears its European heritage on its sleeve. Home to more than 80 ethnic communities, Montreal is known for its fantastic food and atmospheric streets and neighbourhoods.
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Days 7-8 Boston

Swap French patisseries for Guinness on tap, and discover the fighting Irish spirit of a town that has been dubbed ‘The Athens of America’. Get caught up in the scholarly history of Boston with a trip to Cambridge, explore the Italian district or walk the Freedom Trail to learn about America’s founding fathers.
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Days 9-10 New York

From the moment you spot the looming towers of New York on the horizon, it’s hard not to get caught up in the sheer size of this mega metropolis. From Times Square, Broadway, Central Park and the Empire State Building, there’s so much to see you could spend months just ticking off your to-do list.
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