Win a trip to Chicago, Whistler, Hawaii, Italy or the Mediterranean!

Feeling lucky? Then enter these contests and you might be on your way to Chicago, Whistler, Hawaii or Italy, or off on a Mediterranean cruise. Bonne chance!

Cycle through Tuscany

Move quickly on this one, if you like to combine travel and fitness: The Oprah Magazine is giving away a six-day cycling trip for two on Italy’s Tuscan Coast, including flights, accommodations, many meals, and a cycling tour with VBT Bicycling and Walking Vacations. Not open to Quebec residents. Contest closes October 9, 2017.

Take three guests to Hawaii

Flickr/Creative Commons photo of a view from the Road to Hana in Maui by Paul Bica.

You’ll be the most popular person in town if you win this prize: a seven-night trip for four to Maui, including airfare on WestJet and accommodations. Who would you bring? I bet your friends and family would have some suggestions. This contest is not open to Quebec residents. Contest deadline is October 15, 2017.

Live it up in Whistler

To promote the movie The Mountain Between Us, Postmedia is giving away a goodie-packed trip for two to Whistler, B.C. The prize includes flights to Vancouver, ground transportation from Vancouver to Whistler, four nights at the Westin Resort and Spa, a helicopter tour, a mountaintop fondue tour, spa treatments, and restaurant gift certificates. Open to all Canadians of legal age, and you can enter once a day. Entry deadline is October 17, 2017.

Escape to Chicago for the weekend

The Chicago skyline reflected in water.

Flickr/Creative Commons photo of the Chicago skyline by Roman Boed.

To celebrate the release of Pearl Jam’s new concert film, Let’s Play Two, Postmedia is giving away a two-night trip for two to Chicago (where the concert was filmed), including airfare and accommodations. Open to all Canadians of legal age. Contest closes on October 29, 2017.

Cruise the Mediterranean

Stokes is giving away a seven-night Mediterranean cruise for two, including airfare. The estimated value of the prize is $4,500. Open to all Canadians of legal age. Entry deadline is October 29, 2017.

I publish a contest roundup early each week on this site. Do you want to be sure never to miss one? And would you like more tips on road trips from Ottawa—including info on hotel discounts, festivals and other cool news? Subscribe to my free weekly e-newsletter! I will never spam you—promise.

All attempts have been made to make the information here as correct as possible, but in the case of a discrepancy between the details in this post and the details on each contest’s website, the information on the contest’s website will be deemed correct. These contests are the responsibility of the contest sponsors, not OttawaRoadTrips.com. Contests may end before midnight on the date indicated. Even if this post is shared on Facebook, that does not imply that any of these contests are sponsored, endorsed or administered by, or associated with, Facebook.

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