Epic Cityscapes New York to Chicago
New
Kick off your adventure in the bustling streets of New York for an exciting 14-day tour ending in the vibrant city of Chicago. Dive into the iconic sights of New York, from Central Park to Times Square, before heading to historic Boston and experiencing quaint Woodstock. Cross into Canada to explore lively Montreal and charming Quebec, with highlights like Parc Mont Royal and Chateaux Frontenac. Venture through Canada's stunning landscapes, visit Ottawa's Parliament Buildings, and cruise the majestic Thousand Islands. Glide past legendary Niagara Falls before re-entering the US to uncover Detroit's rich history. Wrap up in the Windy City, savouring Chicago's spectacular architecture and vibrant urban life. Expect an unforgettable mix of cityscapes, cultural landmarks, and scenic wonders.
For a detailed itinerary and information about visas, money, weather and more.
Tour Overview
Duration
14 daysHotel Rating
3-4 star hotelsStarts
New YorkEnds
ChicagoMinimum age
No minimum ageMaximum age
100Arrival Transfer
YesDeparture Transfer
NoTour Guide
Yes - English speaking guides (guiding may be in additional languages to English)Countries
Canada, USAPassengers
$3,855.00
$400.00
Tour Style
Group Size
Min 1 / Max 65
Trip Type
Large Coach Tours
Range
This tour is operated by our trusted local partner and has been handpicked by us to deliver you an unforgettable trip.
Guiding Style
This tour includes scheduled sightseeing with expert guides in key destinations as per the Inclusions, as well as transportation (either with a driver or public transport), plus of course your accommodation. There is no single tour guide or tour leader throughout the trip. You’ll have support where it counts, and more freedom in between. Our cruise tours also fall into this category where you will be looked after by a crew. For more information, check the Inclusions of this tour.
Tour Pace
A balanced pace, with a mix of free time and visits to multiple locations, allowing for both relaxation and exploration. Generally doesn't visit more than one or two destinations per day.
Physical Rating
A moderate amount of walking is required during sightseeing, with some free time, offering a balance between activity and relaxation. As a general rule, you should be able to walk 2-kilometres without stopping.
Tour Guide
Yes - English speaking guides (guiding may be in additional languages to English)Group Size
Min 1 / Max 65Tranportation
N/ALanguage
EnglishLanguage
EnglishRange
This tour is operated by our trusted local partner and has been handpicked by us to deliver you an unforgettable trip.
Guiding Style
This tour includes scheduled sightseeing with expert guides in key destinations as per the Inclusions, as well as transportation (either with a driver or public transport), plus of course your accommodation. There is no single tour guide or tour leader throughout the trip. You’ll have support where it counts, and more freedom in between. Our cruise tours also fall into this category where you will be looked after by a crew. For more information, check the Inclusions of this tour.
Tour Pace
A balanced pace, with a mix of free time and visits to multiple locations, allowing for both relaxation and exploration. Generally doesn't visit more than one or two destinations per day.
Physical Rating
A moderate amount of walking is required during sightseeing, with some free time, offering a balance between activity and relaxation. As a general rule, you should be able to walk 2-kilometres without stopping.
Trip Type
Large Coach ToursPlaces You'll See
New York
Boston
Woodstock
Montreal
Quebec
Sainte-Agathe-des-Monts
Mont-Tremblant
Ottawa
Thousand Islands
Toronto
Niagara-on-the-Lake
Niagara Falls
Detroit
Saugatuck
Chicago
Included
Not Included
Itinerary
Day 1 - New York
Upon your arrival in New York, we'll ensure a smooth transfer to your hotel, allowing you to settle in and enjoy some leisure time. In the afternoon, you will be provided with important information about the upcoming circuiteither directly or via informative panels located in the hotel reception areaso you're well prepared for the adventures ahead. Enjoy your free time exploring the vibrant energy of New York at your own pace. Please note: This tour may have travellers joining or departing at various points along the route, meaning group composition can change during the tour. Please also be aware that depending on group composition, guiding may be in additional languages as well as English.
Day 2 - New York
Following breakfast, we embark on a comprehensive tour of New York City, showcasing the vibrant heart of Manhattan. Our journey takes us through the iconic districts of Upper, Middle, and Lower Manhattan. We will explore Wall Street, known as the financial epicentre of the world, and catch a glimpse of the bustling activity at Rockefeller Center. The stunning St Patricks Cathedral awaits our visit, alongside a stroll through the serene expanse of Central Park. Our tour also includes a stop at noteworthy locations such as Columbus Circle and the AOL Time Warner Building, where modernity meets classic design. Discover the distinct cultures of the Village and Little Italy, each brimming with unique charm. At Battery Park, admire the impressive and panoramic views of the Statue of Liberty standing tall across the harbour. As evening falls, we head to Times Squarethe pulsating core of New York City, famed for its dazzling lights and world-class Broadway shows. If our hotel is conveniently located in the Times Square area, enjoy easy access without the need for additional transportation.
Day 3 - New York - Boston
We set off for Boston, Massachusetts, in the morning. Upon arrival around midday, we'll embark on a panoramic tour of this city, which played a pivotal role in American Independence. Our stops include Beacon Hill, the historic Harvard University, and the inviting gardens of Boston Common. You'll also admire the architecture of Trinity Church before we conclude our tour at the bustling Quincy Market. This lively area near the docks, teeming with shops and eateries, offers you some free time to explore before we head to our hotel for the evening.
Day 4 - Boston - Woodstock - Montreal
Following breakfast, we'll journey through New Hampshire and Vermont, two of the Eastern US states celebrated for their breathtaking landscapes. Our first stop is Woodstock in Vermont, a picturesque town renowned for its beautifully restored Georgian houses. After exploring, we'll continue our travels, crossing the Canadian border and arriving in the vibrant city of Montreal. Here, you'll have time to settle in at your accommodation and start experiencing the cultural richness of this Canadian metropolis.
Day 5 - Montreal - Quebec
Following breakfast, we'll embark on a panoramic tour of Montreal. Our morning will be filled with visits to key sites, including Parc Mont Royal, St. Joseph's Oratory, and the Cathedral. After lunch, we'll set off for Quebec, where we'll arrive in the evening and settle in for our accommodation.
Day 6 - Quebec
Following breakfast, we embark on a morning panoramic tour of Quebec City, where we'll explore iconic landmarks such as the Chteau Frontenac, Place Royale, Sainte Anne de Beaupr, and the Citadelle. These sites offer a glimpse into the city's rich history and architectural beauty. The afternoon is yours to enjoy at leisure. We recommend visiting the Montmorency Falls, a striking natural attraction. Take time to soak up the surroundings and discover more of what Quebec has to offer.
Day 7 - Quebec - Sainte-Agathe-des-Monts - Mont-Tremblant - Ottawa
Following breakfast, we embark on a journey through the picturesque Canadian landscapes. Our first stop will be the captivating Laurentian Hills, known for their stunning natural beauty. We will pause in the quaint town of Sainte-Agathe-des-Monts, a charming setting that perfectly showcases the regions allure. Our journey then continues to Mont-Tremblant, renowned for its world-famous ski resort and breathtaking scenery. After enjoying the sights here, we press on to Ottawa, the capital city of Canada. Upon arrival, we settle in for our stay and prepare to explore this vibrant city.
Day 8 - Ottawa - Thousand Islands - Toronto
Begin your day in Ottawa with a city tour post-breakfast. We will explore the historic Canal Rideau and marvel at the impressive Parliament Buildings. If you're travelling in July or August, youll have the opportunity to witness the colourful Changing of the Guard ceremony. Our journey continues as we head to Gananoque the gateway to the Thousand Islands. Here, well embark on an enchanting sightseeing cruise along the St. Lawrence River, showcasing the captivating scenery and numerous islands that dot the water. After the cruise, we proceed southwards, reaching Toronto in the late afternoon, where we will settle into our hotel for the evening.
Day 9 - Toronto
Following breakfast, we embark on a guided sightseeing tour of Toronto, characterised by its vibrant cultural and architectural landmarks. We'll explore the bustling Chinatown, the modern City Hall, and the dynamic Financial District, concluding at the renowned Eaton Centre. The historic charm of Casa Loma and other key tourist attractions are also on our itinerary. In the afternoon, you may choose to ascend the iconic CN Tower for panoramic city views, indulge in some shopping at Eaton Centre, or discover the Underground City a vast network of shopping galleries beneath the Financial District. As evening descends, you have the option to visit Queens Quay, a vibrant waterfront area teeming with restaurants. Accommodation will be provided for the night.
Day 10 - Toronto - Niagara-on-the-Lake - Niagara Falls
After breakfast, we'll journey to the charming town of Niagara-on-the-Lake, known for its picturesque streets and vibrant atmosphere. You'll have time to explore this delightful area at your leisure. We then continue our adventure to the majestic Niagara Falls. Upon arrival, we'll pause to capture photos of the impressive Floral Clock before embarking on the Hornblower Niagara Cruise. This exhilarating boat ride takes us right to the base of the iconic falls, offering an unforgettable perspective. Following our cruise, you'll have free time to enjoy the attractions at Clifton Hill, known for its lively entertainment options. We will conclude our day with an arrival at our hotel in Niagara Falls in the late afternoon, where you can relax and soak in the breathtaking surroundings.
Day 11 - Niagara Falls - Detroit
Today, we journey onwards through the charming and diverse landscapes of Canada, making our way to the city of Windsor. Here, we pause to take in the stunning views of the Detroit skyline from Windsor's picturesque Riverfront. Our adventure continues as we visit the renowned Henry Ford Museum, where admission is included, allowing you to explore the rich tapestry of American history and innovation showcased within. Following this cultural excursion, we move on to explore the vibrant city of Detroit itself. In the evening, you'll have the opportunity to savour the lively atmosphere and delightful dining options in the neighbourhood of Greektown. After an enriching day, we return to our accommodation for a restful night.
Day 12 - Detroit - Saugatuck - Chicago
We begin our day with an early departure from Detroit, traversing the state of Michigan to reach the charming town of Saugatuck. Here, you'll have time to explore the inviting shopping streets and perhaps enjoy a leisurely lunch. Our journey continues as we make our way to the vibrant city of Chicago. In the afternoon, we will transfer you to Millennium Park, a celebrated public space known for its innovative architecture and art installations. From there, we'll venture to The Loop, a bustling neighbourhood famed for its theatres and vibrant neon lights. The evening is yours to enjoy as you wish perhaps savour a dinner at one of the local eateries and take in the city's lively atmosphere. We will conclude the day with accommodation in Chicago, ready for a new adventure tomorrow.
Day 13 - Chicago
After enjoying breakfast, we embark on an insightful panoramic tour of Chicago, unveiling the city's most significant landmarks. We start at the modern Millennium Park, then marvel at the towering Willis Tower and explore Grant Park. Our journey includes experiencing the vibrant atmosphere of The Loop with its iconic elevated train and delving into Downtowns bustling streets. We continue to the Museum Campus, home to the Adler Planetarium, The Field Museum of Natural History, and the Shedd Aquarium. As we cross the bridges over the Chicago River, we are treated to a stunning panoramic view of the city from the lake. Spend the rest of the morning at your leisure, perhaps exploring the city centre or taking in breathtaking views from the Willis Tower. Enjoy free time to have lunch and visit Navy Pier, a hub of entertainment transformed into the epicentre of the city's leisure activities since its inception in 1916. Optionally, consider taking a renowned water tour along the picturesque Chicago River, which showcases the citys distinct and striking architecture. We conclude our day with accommodation in Chicago.
Day 14 - Chicago
On the final day, after enjoying breakfast, our services will conclude in Chicago.
Tour Reviews
Extras and add-ons
If you'd like to add extras or add-ons to your booking, you can do this easily during checkout. Just review the available options and select any additional services or upgrades you'd like before completing your purchase.
Pre and Post Tour Accommodation
Extend your tour with us by booking pre and post-accommodation, available at a per-person, per-night rate.

Pre-Tour Accommodation - New York
XXX
Triple
Double
Twin
Single
Hotels
The hotels listed below are examples which we frequently use on this tour. Alternative hotels of a similar standard may be used instead.
Confirmation of the hotels used may not be available until 48 hours before the tour departs.
If you are interested in booking pre or post-tour accommodation, here are some of the hotels we typically use.
Prices & Dates
Departure dates are guaranteed with 2 travellers. 'Double/Twin' prices are per person when there are 2 people on the same booking sharing a room. 'Single' prices are applicable to anyone wanting the privacy of their own room. 'Triple' prices are per person when there are 3 people on the same booking sharing a room. 'Shared' prices are for solo travellers who are happy to share with another solo traveller of the same sex in a twin room - a single room will be provided at no additional cost if there are no suitable travellers to share with.
Can't find a date that works for you?
Dates for 2027 haven't been released yet.
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