Boston to Windsor flights. Book flights today with Porter Airlines (2022)

Barrels of fun

Fly from Boston to Windsor, for a taste of rum-running history.

During Prohibition, Windsor was the source of sought after alcohol for thirsty Americans. Now, this illicit history has been distilled into some of the best things to do in Windsor. Historical buildings, museums, and heritage parks make this former rum-running hotspot the toast of Southern Ontario.

Although much has changed since the days of smuggling whisky across the Detroit River, Windsor still knows how to have fun. For the best of the city’s entertainment, you can always bet on a good time at Caesars Windsor. At the WFCU Centre, even more amusement awaits, with concerts, theatrical performances, and hockey all under one multi-purpose roof.

Drink in Windsor’s historic points of interest by touring through the Canadian Club Brand Centre and Walkerville Brewery. After tasting Windsor’s famous whisky and beer at these beverage institutions, you’ll want to raise a glass to Windsor’s rebellious past.

Historic buildings throughout the city shine a light on life in Windsor throughout the years. From the cozy company housing of Olde Walkerville to the grand estate grounds of Willistead Manor, these structures are your window into a bygone Windsor.

Several of the city’s heritage structures come together to celebrate local history in Windsor’s Community Museum. Local artistry is on display in Windsor’s former jail and courthouse, the MacKenzie Hall Cultural Centre. In the Art Gallery of Windsor’s modern building, you’ll find 4,000 of the city’s finest works of art.

30 more pieces of the Windsor’s art collection are scattered along the city’s waterfront, in the Windsor Sculpture Park. Before you go back to Boston, be sure to enjoy the park’s art and the view of the sparkling Detroit River, the former route of Windsor’s rumrunners.

Boston to Windsor flights. Book flights today with Porter Airlines (1) Boston to Windsor flights. Book flights today with Porter Airlines (2)

Downtown Detroit

Boston to Windsor flights. Book flights today with Porter Airlines (3)

Just across the river

Travel back across the US border during your trip from Boston to Windsor, with a day in downtown Detroit.

To get to Detroit, take the speedy Detroit Windsor Tunnel directly into downtown, or ride the scenic Ambassador Bridge over the Detroit River. Whether you go under or over the water, you won’t have to go far to reach Windsor’s American neighbour.

After admiring Detroit’s distinct skyline from Windsor’s waterfront, get a closer look at these striking structures. From the seven skyscrapers that make up the metallic Renaissance Center, to the 40 storey red brick walls of the 1929 Guardian Building, Detroit features a variety of interesting architectural features.

Several historic buildings act as the main stage for downtown Detroit’s arts scene. Both the Fox Theatre and Fillmore Detroit date back to the 1920s, and still light up the stage with some of Detroit’s top billed acts.

For more modern entertainment, the MGM Grand Detroit hosts live shows, lounges, and nightclubs. Double down on Detroit’s exciting casinos at the Greektown Casino-Hotel, with a variety of gaming and dining options.

Detroit’s entertainment offerings continue in the outdoors at Philip A Hart Plaza. During the summer, this public space hosts the annual Detroit Jazz Festival, which spreads from the Plaza to Campus Martius.

If you miss out on this spectacular concert series, take a shot at Detroit’s sports offerings. At Joe Louis Arena, the Detroit Red Wings take to the ice, while Comerica Park hosts the home runs of the Detroit Tigers. The city’s other big cat team, the Detroit Lions, aim for the touchdown on Ford Field. With so many sporting venues, it’s always game time in Detroit.

Before you return to Windsor, take some time to enjoy downtown Detroit’s surrounding attractions. Whether you head north to Troy, Michigan for amazing shopping, or go south to the beautiful Belle Isle Park, a day in Detroit will be one of the best parts of your trip from Boston.

Ojibway Prairie Complex

Boston to Windsor flights. Book flights today with Porter Airlines (4)

A natural beauty

After your flight from Boston touches down, stretch your legs in the fascinating ecosystems of the Ojibway Prairie Complex.

Started in 1957, with a humble area of 100 acres, the Ojibway Prairie Complex has since grown to six times its original size. Now, with 600 untamed acres to its name, this nature reserve is home to some of Windsor’s most striking scenery.

Five separate parts compose this collection of ecosystems, including the well-loved Ojibway Park. In Ojibway Park, the Nature Centre outlines the animals and plants that live in the park. Along with this educational information, the Centre also hosts wildlife, wildflower, photography and birding programs to enhance your exploration of the outdoors.

Keep an eye out for the park’s animal population as you make your way through the wilds of Ojibway. Ranging from the rare blanding’s turtle, to white-tailed deer, and green herons, the park hosts a colourful collection of creatures. Some of these species aren’t seen anywhere else in Ontario, making Ojibway ecologically unique.

Even if you don’t manage to catch a glimpse of the animals living in Ojibway, you can always count on spotting the area’s plant life. Oak savanna and endangered Ontario tallgrass prairie stand as some of the few remaining swaths of what was once one of the province’s prominent ecosystems. Among these swaying grasses, you’ll find 60 species specific to prairie areas, and over 500 kinds of flowering plants. Occasionally, the park’s vast greenery goes up in smoke, but don’t panic, these prescribed burns are part of the process of preserving prairie ecosystems.

For the best views of Ojibway’s animals and ecosystems, take one of the many trails that trace through the park. If you’re near the Nature Centre, step onto the Windsor Trail. This expansive route through more of the area’s stunning nature will take you to the next outdoor adventure on your trip from Boston.

How to get to Boston Logan International Airport (BOS)

Porter’s check-in desk is located in Terminal E.

Logan International Airport (BOS) is about 6 km / 4 mi from downtown Boston.

Hotels near Boston Logan International Airport

Looking for a hotel near Boston Logan Airport for accommodation before your flight? Here are some hotels close to the airport:

Hilton Boston Logan Airport

Hyatt Regency Boston Harbor

Hilton Garden Inn Boston Logan Airport

Courtyard by Marriott Boston Logan Airport

Renaissance Boston Waterfront Hotel

And more…

For pricing and reservations, please check the hotel website.

Transportation to Boston Logan International Airport

Water taxis from downtown cost about $15 USD.

Ride-hailing apps such as Uber and Lyft offer services to Boston Logan International Airport. Passengers may only be dropped off on the upper Departures level of each terminal at Boston Logan.

Take the Massachusetts Bay Transit Authority Silver Line SL1 bus to any one of the airport terminal stops. The fare is $2.25 USD.

The Logan Express shuttle bus provides service to the airport from downtown. The fare is $3.00 USD by credit/debit only.

Please allow sufficient time to drop off your car rental before your departing flight.

Taxis from downtown cost about $25 USD. Car service costs about $80 USD.

Boston Logan International Airport Parking

Driving to Boston Logan International Airport? There are many parking options at Boston Airport with convenient access to all terminals. Choose from the Central Parking Garage, Terminal B Garage or Terminal E Lots, with rates starting at $35 USD per day.

The information and figures above are for reference only, and may not be current. Please visit each airport's website for up-to-date details.

Landing in Windsor

Windsor International Airport (YQG) is about 10 km / 6 mi from downtown Windsor.


Car rental services are available across from the domestic baggage claim area of Windsor International Airport (YQG).

Taxis to downtown cost about $25 CAD. Car service costs about $35 CAD.

Take the Transit Windsor 8 Walkerville bus from the stop at the Windsor International Transit Terminal. The fare is $3.00 CAD.

The information and figures above are for reference only, and may not be current. Please visit each airport's website for up-to-date details.

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