{"id":34650,"date":"2026-03-05T10:20:00","date_gmt":"2026-03-05T15:20:00","guid":{"rendered":"https:\/\/marathontours.com\/en-us\/events\/chicago-marathon-2\/"},"modified":"2026-03-13T10:49:05","modified_gmt":"2026-03-13T14:49:05","slug":"windy-city-to-waterfront-challenge","status":"publish","type":"events","link":"https:\/\/marathontours.com\/en-us\/events\/windy-city-to-waterfront-challenge\/","title":{"rendered":"Windy City to Waterfront Challenge"},"content":{"rendered":"","protected":false},"excerpt":{"rendered":"","protected":false},"featured_media":34655,"template":"","event_types":[110,20,106,104,99],"event_locations":[28],"event_distances":[32,11,12],"event_course_types":[21],"event_seasons":[22],"class_list":["post-34650","events","type-events","status-publish","has-post-thumbnail","hentry","event_types-5k","event_types-abbott-world-marathon-majors","event_types-half-marathon","event_types-marathon","event_types-urban","event_locations-north-america","event_distances-5k","event_distances-half-marathon","event_distances-marathon","event_course_types-abbot-world-marathon-majors","event_seasons-autumn"],"acf":{"event_hero_image":34618,"event_logo":"","event_logo_background":{"enable":true,"background_colour":""},"event_status":"available","event_status_labels_available":"book-now","event_status_labels_waitlist":"available-soon","event_status_labels_off_sale":"sold-out","event_waitlist_button":{"link_option":"external","":null,"external_link":{"title":"Available Soon","url":"mailto:kaitlyn.roukey@marathontours.com","target":"_blank"}},"event_additional_buttons":null,"event_book_button":{"link_option":"external","":null,"external_link":{"title":"Book Now","url":"https:\/\/bookingus.marathontours.com\/experience\/windy-city-to-waterfront-challenge-2026\/38","target":"_blank"}},"event_extra_button":"","event_overview":"

If you have questions regarding Marathon Tours & Travel's Windy City to Waterfront Challenge Package please: CONTACT US<\/a>\u00a0or\u00a0CALL 617-242-7845<\/a><\/p>\r\n

Join us for the 2026 Windy City to Waterfront Challenge<\/strong> and conquer the famed Bank of America Chicago Marathon & TCS Toronto Waterfront Marathon in one unforgettable week. Start in Chicago on a lightning\u2011fast, spectator\u2011packed course that winds through the city\u2019s diverse neighborhoods 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.<\/p>\r\n

The Bank of America Chicago Marathon<\/strong> is known worldwide for its fast, flat course and its thrilling world-class athlete competition. O<\/span>ne 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 neighborhoods including colorful Old Town, Little Italy and Chinatown. As an official tour operator, Marathon Tours & Travel can offer guaranteed race entry with our package.\u00a0<\/span><\/p>\r\nThe TCS Toronto Waterfront Marathon<\/strong> is one of Canada\u2019s 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\u2019s diverse neighborhoods and iconic waterfront. With crisp autumn weather and an electric race day atmosphere, it\u2019s a great time to experience Toronto!<\/span>\u00a0<\/span>\r\n\r\nThe Windy City to Waterfront Challenge<\/strong>\u00a0combines these two renowned races into one exhilarating ten-night package where you can make the most out of these bucket-list destinations.\r\n\r\nBoth the Bank of America Chicago Marathon and TCS Toronto Waterfront Marathon are AbbottWMM Marathon Tours & Travel World Age Group Qualifying Races<\/a>.<\/span>","event_overview_button":"","event_feature_icons":null,"event_features":{"meals_included":{"detail":"Meals as outlined on the itinerary","title":"Meals Included"},"guide":{"title":"Guide","detail":"Hosted on-site by Marathon Tours & Travel"},"transfers":{"detail":"Airport transfers as outlined on the itinerary","title":"Transfers"},"trip_extension":{"title":"Trip Extension","detail":""},"accommodation":{"title":"Accommodation","detail":"Ten nights' accommodation"},"entry":{"title":"Entry","detail":"Guaranteed race entry for Chicago Marathon & Toronto Marathon, Half-Marathon or 5K"},"celebration_party":{"detail":"Post-race celebration ","title":"Celebration Party"},"excursions":{"title":"Excursions","detail":""},"helping_hand":{"title":"A Helping Hand","detail":""},"worldwide_events":{"title":"Worldwide Events","detail":""},"medal_bling":{"title":"Medal Bling","detail":""}},"event_gallery":[{"acf_fc_layout":"event_gallery_image","image":794},{"acf_fc_layout":"event_gallery_image","image":10704},{"acf_fc_layout":"event_gallery_image","image":799},{"acf_fc_layout":"event_gallery_image","image":34619},{"acf_fc_layout":"event_gallery_image","image":34620},{"acf_fc_layout":"event_gallery_image","image":34616}],"event_packages":[{"package_title":"Windy City to Waterfront Challenge Package","package_duration":"10 Nights","package_dates":"October 9 - 19, 2026","package_days":[{"day_title":"Friday, October 9","day_content":"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."},{"day_title":"Saturday, October 10","day_content":"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. (<\/span><\/em><\/span>Breakfast included<\/span><\/span>)<\/span><\/span>\u00a0<\/span><\/em>"},{"day_title":"Sunday, October 11","day_content":"Race Day! <\/strong>\r\n\r\nYour 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. (<\/span><\/em><\/span>Breakfast included<\/span><\/span>)<\/span><\/span>\u00a0<\/span><\/em>"},{"day_title":"Monday, October 12","day_content":"After checking out of your respective hotel, please make your way to Chicago O\u2019Hare 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.\u00a0 <\/span>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)<\/em>\r\n\r\nFurther details regarding flight information will be provided at a later date.<\/em><\/span>"},{"day_title":"Tuesday, October 13","day_content":"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)<\/em>"},{"day_title":"Wednesday, October 14","day_content":"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)<\/em>"},{"day_title":"Thursday, October 15","day_content":"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)<\/em>"},{"day_title":"Friday, October 16","day_content":"Today is at your leisure. The Marathon Expo will be open from 10:00am-8:00pm so be sure to visit the Better Living Centre to pick up your bib, race kit, and race day necessities!\u00a0<\/span><\/span><\/span>\r\n\r\nJoin your fellow Marathon Tours & Travel runners and supporters for a Welcome Reception <\/span>in the evening<\/span>.<\/span><\/span> (<\/span><\/em><\/span>Breakfast included<\/span><\/span>)<\/span><\/span>\u00a0<\/span><\/em><\/span>"},{"day_title":"Saturday, October 17","day_content":"Today is race day for the Toronto 5K! After this, you<\/span>\u00a0are free to explore\u00a0<\/span>Toronto<\/span>\u00a0on your\u00a0<\/span>own! It will also be the last day to visit the Marathon Expo and pick up your race bib - make your way to the Better Living Centre between 10:00am-6:00pm to ensure you have all you need for race day. <\/span><\/span><\/span>\r\n\r\nIn the evening, join your MTT team for a pre-race pasta\u00a0<\/span>dinner\u00a0<\/span>to fuel up for race day.\u202f<\/span><\/span>(Breakfast and dinner included)<\/span><\/span>\u00a0<\/span><\/em>"},{"day_title":"Sunday, October 18","day_content":"Race Day!\u202f<\/span><\/span><\/strong>\r\n\r\nT<\/span>he Marriott Downton at Toronto Eaton Centre<\/span>\u00a0<\/span>is conveniently located within a short walking distance of the start and finish line.<\/span>\u00a0<\/span>In the evening, j<\/span>oin us for drinks and bites\u00a0<\/span>t<\/span>o celebrate your accomplishment<\/span>s!\u00a0<\/span>(<\/span><\/em><\/span>Breakfast included<\/span><\/span>)<\/span><\/span>\u00a0<\/span><\/em>"},{"day_title":"Monday, October 19","day_content":"Departure day. If you are heading home, enjoy a leisure morning at the hotel before\u00a0<\/span>checking-out<\/span>\u00a0by 12:00PM.<\/span><\/span>\u00a0<\/span>"}]}],"event_extensions":"","event_extensions_packages":null,"event_packages_and_rates":"

Windy City to Waterfront Challenge<\/strong> Tour | Ten-Night Package: October 9 - 19, 2026<\/h3>\r\n
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Chicago Features:<\/strong><\/div>\r\n<\/div>\r\n<\/div>\r\n
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