Windy City to Waterfront Challenge
Join us for the 2026 Windy City to Waterfront Challenge and conquer the famed Bank of America Chicago Marathon & TCS Toronto Waterfront Marathon in one unforgettable week. Start in Chicago on a lightning‑fast, spectator‑packed course that winds through the city’s diverse neighbourhoods before lining up in Toronto a week later, for a scenic waterfront tour through the heart of Canada’s largest city. Between races, reset in style at Niagara Falls where you’ll experience the legendary Maid of Mist boat tour capped off by a farewell dinner overlooking the illuminated cascades.
The Bank of America Chicago Marathon is known worldwide for its fast, flat course and its thrilling world-class athlete competition. One of the Abbott World Marathon Majors, the Bank of America Chicago Marathon is a great choice if you want to chase after a personal best or simply finish your first marathon. Packed with spectators, the scenic course will take you past many historic landmarks and through numerous diverse neighbourhoods including colourful Old Town, Little Italy and Chinatown. As an official tour operator, Marathon Tours & Travel can offer guaranteed race entry with our package.
The TCS Toronto Waterfront Marathon is one of Canada’s premier running events, offering Marathon, Half-Marathon, and 5K distances through the heart of vibrant downtown Toronto. This scenic and energetic race takes runners on a tour of the city’s diverse neighbourhoods and iconic waterfront. With crisp autumn weather and an electric race day atmosphere, it’s a great time to experience Toronto!
The Windy City to Waterfront Challenge combines these two renowned races into one exhilarating ten-night package where you can make the most out of these bucket-list destinations.
Both the Bank of America Chicago Marathon and TCS Toronto Waterfront Marathon are AbbottWMM Marathon Tours & Travel World Age Group Qualifying Races.
Meals Included
Meals as outlined on the itinerary
Guide
Hosted on-site by Marathon Tours & Travel
Transfers
Airport transfers as outlined on the itinerary
Accommodation
Ten nights' accommodation
Entry
Guaranteed race entry for Chicago Marathon & Toronto Marathon, Half-Marathon or 5K
Celebration Party
Post-race celebration
Coopah
2 week free trial for Coopah training plans
Travel Package Information
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Itinerary
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Friday, October 9
Arrive in Chicago and transfer on your own to your hotel. You will be greeted at your hotel by a Marathon Tours & Travel staff. The Abbott Health & Fitness Expo at McCormick Place will be open today. This evening enjoy a Welcome Reception with your hosts and running peers. The rest of the evening is free to enjoy this beautiful city.
Saturday, October 10
We start the day with an optional shakeout run along the Riverwalk to loosen your legs. The rest of your morning and afternoon are free on your own. Our pre-race pasta dinner will take place this evening. (Breakfast included)
Sunday, October 11
Race Day!
Your Marathon Tours & Travel team will be in the lobby of the hotel offering escorted walks to the start area in Grant Park. Following the race, you will make your way back to your hotel for some well-deserved rest before we gather for a celebratory toast! The evening is free to experience one of the many fine restaurants in the city. (Breakfast included)
Monday, October 12
After checking out of your respective hotel, please make your way to Chicago O’Hare International Airport for your midday flight to Buffalo International Airport. An MTT rep will be on-site to meet the and check our group into the flight. Upon arrival, we will have a private transfer to the Marriott on the Falls hotel. The rest of your day is on your own. (Breakfast included)
Further details regarding flight information will be provided at a later date.
Tuesday, October 13
After breakfast, join us for the iconic Maid of the Mist Niagara Falls boat tour. This afternoon will be on your own. Tonight, join us for a farewell dinner overlooking Niagara Falls. (Breakfast and dinner included)
Wednesday, October 14
This morning we will have a private transfer to your hotel in Toronto. After checking into the Marriott Downtown at CF Toronto Eaton Centre, the rest of the day will be on your own. (Breakfast included)
Thursday, October 15
Today, join us for an optional city tour of Toronto. The tour will include a stop and visit at the CN Tower, a scenic Toronto City Harbour Cruise, a stop at St. Lawrence Market, and more! The rest of your day will be on your own. (Breakfast included)
Friday, October 16
Today is at your leisure. Join your fellow Marathon Tours & Travel runners and supporters for a Welcome Reception in the evening. (Breakfast included)
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Packages & Rates
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Windy City to Waterfront Challenge Tour | Ten-Night Package: October 9 – 19, 2026
Chicago Features:- Three nights hotel accommodation
- All hotel taxes
- Welcome Reception on Friday evening
- Shake-out run on Saturday morning
- Saturday Morning Architectural River-Cruise – Optional Addition
- Pre-race dinner on Saturday evening
- Escorted walk to the start area (less than one mile from the hotel!)
- Post-race celebration on Sunday evening
- Services of Marathon Tours & Travel staff at the hotel
- Guaranteed Entry is an additional cost ($640)
Niagara Features:
- Monday flight from Chicago (ORD) to Buffalo (BUF)
- Transfer from Airport to Marriott on the Falls
- Two nights’ accommodation at the 4* Marriott on the Falls
- Maid of the Mist ticket
- Farewell dinner in Niagara
- Transfer from Niagara to Toronto
- Two nights’ accommodation at the 4* Marriott Downtown at CF Toronto Eaton Centre
- Daily Breakfasts
- Hotel taxes
Toronto Features:- 3 nights’ accommodation at 4* Marriott Downtown at CF Toronto Eaton Centre
- Daily breakfasts, except on arrival day
- Hotel taxes
- Welcome drink and reception
- Shakeout run
- Pre-race pasta dinner
- Post race drinks and celebration
- Guidance and support from Marathon Tours & Travel in Toronto
Please Note:
- Entry only is not allowed.
- Room types available are Double Rooms (one bed/ two persons), Twin Rooms (two beds/two persons) or Single (one bed/one person).
- Triple and Quad and Children rates available upon request.
- Additional nights based on request and availability.
- Marathon Tours & Travel’s policy is that anyone staying in our room block must be part of our package. If you plan to bring a spouse or guest, they must purchase our package. For example, if there are two of you, the rate would be the double occupancy rate (per person). If you purchase a single occupancy rate package, then only you are allowed in your room. To attend any of our activities, you must be part of our package.
Not Included:
- Race entry fee
- Meals unless noted above
- Gratuities and tips unless noted above
- Travel Insurance
- Transportation to Chicago & from Toronto
Rates (all prices are per person in GBP)
Additional nights available upon request
Windy City to Waterfront Challenge PackageTen-Night Package Double Occupancy Single Occupancy Windy City to Waterfront Challenge Package £ TBC £ TBC Optional Add-OnsOptional Tours Rate Chicago Architectural River-Cruise £ TBC Toronto City Tour £ TBC Race Entry FeeChicago Marathon Race Entry £ TBC Toronto Marathon Race Entry £ TBC Toronto Half-Marathon Race Entry £ TBC Toronto 5K Race Entry £ TBC
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Hotels
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Renaissance Chicago Downtown Hotel
This hotel is ideally situated in the Chicago Loop and within walking distance of the Chicago Marathon start and finish. From the moment you step into the hotel’s modern lobby, you have everything you need for a first-class stay in the Theatre District. Delight in contemporary hotel rooms near the Riverwalk, each offers a host of fantastic amenities. Many accommodations also boast panoramic views of the downtown Chicago skyline. Take a refreshing swim in the hotel’s heated indoor pool or unwind with a cocktail and creative American cuisine at Raised bar, offering a sensational rooftop setting and a unique, modern ambiance. Style and substance blend seamlessly at Renaissance Chicago Downtown Hotel.
Marriott on the FallsSituated on the brink of Horseshoe Falls in Canada, Niagara Falls Marriott on the Falls is the closest hotel to Niagara Falls. Located in the Fallsview Tourist District near Niagara Falls Convention Centre, Fallsview Casino Resort, Niagara Parks and Niagara City Cruises, the fallsview hotel in Niagara Falls offers breathtaking views, exemplary service and modern amenities.
Marriott Downtown at CF Toronto Eaton CentreThe Marriott Downtown at CF Toronto Eaton Centre is a contemporary full service hotel located steps from premier shopping, dining, and entertainment in the heart of downtown Toronto. Its guestrooms feature comfortable seating areas and modern amenities designed for a relaxing and convenient stay. Guests can enjoy facilities such as a 24hour fitness center, the PAR BAR Topgolf Swing Suite, and a rooftop indoor pool. With major attractions like Nathan Phillips Square, the CN Tower, and Scotiabank Arena within walking distance, it offers an ideal base for exploring the city.
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Event Information
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Chicago Event Information:
Race Date: Sunday, October 11, 2026
Race Time: The first wave begins at 7:30 AM.
Minimum Pace/Cut-Off Time Policy: The event has a course time limit of 6 hours and 30 minutes. The official end vehicle will start following the last starter and maintain a 15-minute per mile pace along the race course. Chicago Marathon Website
Course: Flat and fast, the start and finish is in Grant Park. The looped-course through the city offers numerous opportunities for spectators to catch the action.
Temperature: The Windy City can be just that or it could be a chamber of commerce perfect day. Expect anything and everything from temperatures in the low 40’s Fahrenheit at the start to upper 70s at the finish. The average high and low is 64 and 46 degrees Fahrenheit in October.
Number Pickup: Each runner is responsible for picking up their own race bib and packet at the Abbott Health & Fitness Expo at McCormick Place (2301 S. Martin Luther King Drive, Chicago) from Thursday, October 9 through Saturday, October 11. Find details here.
Difficulty: Easy. This is a flat and fast course.
Toronto Event Information:
Race Date: Sunday, October 18, 2026 (Marathon and Half-Marathon)
The 5K is held the day prior, on Saturday, October 17, 2026.
Start Times:
Marathon – 8:00 AM
Half-Marathon – 8:00 AM
5K – 9:00 AM (October 17)
Course Information:
Marathon (42.2 km)
The Marathon features a 42K course through downtown Toronto and along the waterfront, showcasing more than a dozen neighborhoods and scenic lakefront views. The course is predominantly flat, making it a strong option for fast times and personal bests.
Start Line: Yonge St. near Elm St., facing northbound
Finish Line: Bay St. just north of Queen St., near Nathan Phillips SquareHalf-Marathon (21.1 km)
The Half-Marathon follows the same energetic fall atmosphere and uses segments of the waterfront and downtown Toronto corridors. It is also designed to be flat and fast, offering an approachable course for runners of all levels.
5K
Held the day before the Marathon and Half Marathon, the 5K is a lively, accessible race through downtown Toronto. It serves as a community friendly kickoff to race weekend.
Eligibility:
Marathon: Must be 18+
Half-Marathon: Must be 16+
5K: Open to all ages
Time Limit: Marathon: 6 hours
Aid Stations: Hydration and aid stations are located approximately every 3 km, offering water and endurance fuel products (specific brands/flavors to be confirmed).
Awards / Finisher Items: All Marathon finishers receive
- Finisher Medal
- ASICS Souvenir Shirt
- Postrace recovery food
Temperature: Toronto’s mid October weather is typically cool and variable, offering favorable running conditions.
Difficulty: All three distances are characterized by a primarily flat course, with gentle elevation changes—ideal for runners seeking speed or a supportive, confidence building race experience.
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Registration & Booking
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Rates: All prices are based on current exchange rates and may change due to currency fluctuations.
Reservations and Payments: When you confirm your booking, we will take a deposit payment. Subsequent payments are taken automatically.
Not included in price: All items not specifically listed under tour features. Entry fee is additional. Airfares.
Insurance: We strongly recommend travellers to take out comprehensive travel insurance with sufficient healthcare cover. Make sure that you are insured for existing medical conditions, any activities you plan to do and any equipment that you plan to take. Travel insurance covers you if anything doesn’t go to plan before you travel as well, so we recommend sorting it at the time of booking. For more information, click here.
Security Policy: Marathon Tours & Travel’s security policy requires that anyone staying in our room block must be registered as part of our package. If a registered client attempts to house a non-registered guest and/or invite them to attend any of our scheduled activities, the registered guest’s tour package will be forfeited and parties may be denied access to future tours. Please note that no exceptions will be made as this policy will be strictly enforced.
Responsibility: These tours are operated by Marathon Tours, Inc. of Chelsea, MA who acts only as an agent for the passenger to the companies offering such services and assumes no liability for injury, damage, loss, accident, delay or irregularity caused by any reason whatsoever by any party offering such services. All terms and conditions offered are governed by the laws of Massachusetts. The right is reserved to cancel the tour prior to departure with a refund, less applicable credit card and processing fees, made as full settlement to the passenger. The right is reserved by Marathon Tours, Inc. to deny acceptance of a booking application by any person. Marathon Tours, Inc. may make any changes or alterations in the itinerary as it deems necessary for the proper handling of the tour. The sole responsibility of any airline used is limited to that set out in the passenger contract evidenced by the ticket. The airlines concerned are not to be held responsible for any act, omission or event during the time that the passengers are not on board their aircraft.
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Seven Continents Club ®
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The Seven Continents Club (SCC) offers a unique opportunity for runners to run on all seven continents of the globe, as well as providing numerous benefits to its members. The club operates as a global frequent traveller club for runners, offering waitlist priority for high-demand events, early pre-registration periods for a number of races in popular destinations and tour package vouchers for money off international tour packages. What’s more, Seven Continents Club rewards all its members for the extraordinary achievement of running marathons on each continent with their own special finishers medal and certificate of completion. Join the SCC today!
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Abbott World Marathon Majors Age Group World Championship
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These events are Abbott World Marathon Majors Marathon Tours & Travel Age Group World Championship (AGWC) Qualifying Races. If you achieve the automatic qualifying time for your age group, found here, you will be invited to the 2028 Age Group World Championship Race.
For more information on the Age Group World Rankings and Championship go here.
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