Enchanting Cities Toronto to Chicago Adventure
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Start your adventure in the vibrant city of Toronto and end in the architectural paradise of Chicago over a fulfilling 7-day journey. Begin by exploring Torontos iconic attractions from bustling Chinatown to the historic Casa Loma. Head to Niagara-on-the-Lake and experience the awe-inspiring Niagara Falls with a thrilling Hornblower Cruise. Continue into the United States, with a pit stop at the fascinating Henry Ford Museum in Detroit. In Chicago, marvel at landmarks like the Willis Tower and the scenic Millennium Park. With lively neighbourhoods, spectacular views, and diverse sights, this tour promises an unforgettable cultural and scenic exploration of North America.
For a detailed itinerary and information about visas, money, weather and more.
Tour Overview
Duration
7 daysHotel Rating
3-4 star hotelsStarts
TorontoEnds
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
$1,915.00
$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
Toronto
Niagara-on-the-Lake
Niagara Falls
Detroit
Saugatuck
Chicago
Included
Not Included
Itinerary
Day 1 - Toronto
Upon arriving in Toronto, you'll be warmly welcomed and transferred to your hotel, where you can enjoy some leisurely free time. As you settle in, youll receive important details about the upcoming circuit. If you prefer, feel free to check the informative panels in the hotel reception area for further information. 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 - Toronto
Following breakfast, we embark on a guided sightseeing tour of Toronto, visiting key attractions such as Chinatown, City Hall, the Financial District, Eaton Centre, and Casa Loma, among other notable sites. In the afternoon, you may choose to explore the CN Tower, indulge in some shopping at Eaton Centre, or wander through the Underground City, which features 25 kilometres of shopping galleries beneath the financial district. As evening approaches, consider heading to Queens Quay, a bustling area known for its vibrant atmosphere and numerous dining options to spend your leisure time. Accommodation is included for the night.
Day 3 - Toronto - Niagara-on-the-Lake - Niagara Falls
Following breakfast, we set off to explore the charming town of Niagara-on-the-Lake. After a leisurely stroll, we continue our journey to the world-renowned Niagara Falls. Here, we take the opportunity to capture stunning photos of the Floral Clock before embarking on the Hornblower Niagara Cruisea small boat that brings us up close to the breathtaking falls. Afterwards, youll have time to explore the vibrant attractions of Clifton Hill. In the late afternoon, we arrive at our hotel in Niagara Falls for an overnight stay.
Day 4 - Niagara Falls - Detroit
Today, we journey further through Canada, arriving in Windsor, where we pause at the scenic Riverfront. Here, you can take in the serene views across the river towards Detroit. Our exploration continues as we visit the renowned Henry Ford Museum, with admission included. After immersing ourselves in the rich history and innovation showcased here, we head into the city itself. You'll have the opportunity to spend time in the vibrant district of Greektown, where a variety of dining options await for a delightful dinner. Afterwards, we return to the hotel for the night.
Day 5 - Detroit - Saugatuck - Chicago
We begin our day early, departing from Detroit and travelling through the scenic state of Michigan until we reach the charming town of Saugatuck. Here, you will have time to explore the delightful shopping streets and enjoy a leisurely lunch. Our journey then continues towards Chicago, where we will transfer you to the vibrant Millennium Park in the afternoon. Explore The Loop, renowned for its theatres and dazzling neon lights, and take the opportunity to savour dinner at one of the areas many restaurants. The evening is yours to explore, with accommodation provided for the night.
Day 6 - Chicago
Following breakfast, we'll embark on an extensive tour of Chicago, showcasing its most iconic sites. Highlights include the New Millennium Park, Willis Tower, and Grant Park. We'll journey through The Loop, witnessing the elevated train, and explore Downtown's bustling atmosphere. Our tour also features the Museum Campus, home to the Adler Planetarium, The Field Museum of Natural History, and Shedd Aquarium. As we traverse the bridges over the Chicago River, enjoy breathtaking views of the skyline from the waterfront. For the rest of the morning, you're free to stroll through the city centre or enjoy the view from Willis Tower. Lunch offers a perfect opportunity to explore the culinary delights of Chicago. Don't miss Navy Pier, a hub of urban recreation and once the world's largest pier when constructed in 1916. If you fancy, indulge in a water tour along the Chicago River, complete with the city's stunning architectural vistas. Accommodation is arranged for the evening, providing a comfortable end to an enriching day.
Day 7 - Chicago
Following breakfast, our services conclude and you'll have the day to explore Chicago at your leisure. Whether you choose to delve into the city's vibrant cultural scene or simply relax and soak in the atmosphere, there's no shortage of options. You might opt to revisit favourite spots or discover new areas, ensuring a memorable end to your journey.
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 - Toronto
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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