Fly from Chicago to Windsor and uncover the deep roots of this Ontario border city.
Discover its vibrant art and history through a tour of Windsor’s points of interest. Visit the city’s informative museums, elaborate public artwork, and iconic residences. Explore the artistic legacy of the city at the Art Gallery of Windsor. The gallery is home to an eclectic artwork collection including a 300-year-old English tapestry.
Outside, hit the Riverfront Trail for some fresh air and exercise. The waterfront route breezes by the Art Gallery of Windsor and will lead you to the Windsor Sculpture Park. Here, the grounds are dotted with large-scale sculptures that add a modern touch to your tour.
Mosey along the shores of the Detroit River for views of the city’s historic homes. Make your first stop at Maison François Baby House. Now, the residence is a National Historic Site and part of Museum Windsor. As one of Windsor’s oldest buildings, it houses many of the city’s turn of the century artifacts.
Interestingly, the neighbouring heritage building, the Duff-Baby House was built as a fur trading post in 1798. Now, the sounds of city residents haunt the corridors of this community meeting spot. To get the real haunting effect, you may need an appointment if you plan on wandering through its rooms.
Cap off your journey at the Ambassador Bridge. Connecting the United States and Canada since 1929, sunsets create the perfect backdrop against the bridge’s suspended towers. Capture a postcard-worthy photo filled with the gold and amber hues of the fading sunshine.
Touch down on the scenic banks of the Detroit River with flights from Chicago to Windsor.
Hop off your flight from Chicago to Windsor into Walkerville, the city’s elegant distillery district.
This charming enclave was developed by whisky pioneer Hiram Walker and retains much of its 19th-century flair. Walkerville is distinct from other parts of Windsor with its amazing architecture, inviting green spaces, and a hip cultural scene.
Willistead Manor, a sprawling Tudor-style mansion, is a must-see Windsor attraction. The interior is decorated with polished wood-panelled walls and immaculate crown-molded ceilings. Built in 1906, the cool grey brick exterior will draw you into this former property of the Walker family.
Step through the conservatory on the first floor, into the lush gardens of Willistead Park. Windsor is often called the City of Roses, and it stays true to its name here. In a section of the gardens dedicated to local hero and former Prime Minister Paul Martin, you’ll find a wild array of Windsor’s famed flowers.
Opt for the less heroic, but vividly entertaining stories from the Prohibition Era during your visit to Windsor from Chicago. Walkerville’s winding trails were once the hidden routes of crafty bootleggers. The Chicago Outfit and Al Capone were among their famed clientele, back when Canadian liquor was whisked across the Detroit River.
Drop into the Olde Walkerville Theatre for a snappy rendition of this golden age. The Windsor landmark also hosts an assortment of other live performances, including comedy shows that’ll have you buckling with laughter.
Fancy an urban retreat? Relax in Walkerville’s Lanspeary Park. The park’s summer greenery is only topped by its winter ice rink. Try an afternoon in the Great Western Park for serene riverside views and access to the Riverfront Trail.
Blend a bit of history with a touch of mystery when you fly to Windsor from Chicago.
Watch life unfold along the Detroit River with flights from Chicago to Windsor.
The allure of Riverside comes from the refined green spaces that make it a desirable locale for Windsor residents. There’s little question where the neighbourhood gets its name; owed to its picturesque location beside the river.
Have a camera ready when you set off on an excursion through Riverside. The Pelee Passage Lighthouse is just one of the photo-ready spots along the waterfront. The lighthouse’s tall white tower stands guard over the merger of Lake St. Clair and the Detroit River. It’s an excellent place to watch boats cruise leisurely between Windsor and Detroit.
Nestled at the foot of the lighthouse are the Lakeview Park Marina and Riverside Marina. Come view the bobbing boats, ranging from white sail schooners to stunning luxury yachts.
Biking is highly recommended for traversing the neighbourhood. You’ll have an immersive experience side by side with the locals on paths like Ganatchio Trail. When you’ve worked up an appetite, turn off the trail to a Windsor restaurant on the waterfront. These eateries are renowned for their casual ambiance and delicious cuisine.
Trade in your bike for a kayak and paddle on over to Peche Island. Indulge in a peaceful paddle to the island’s wooded shores. Now a Windsor public park, the island was once owned by whisky baron, Hiram Walker. His abandoned mansion serves as the summer retreat of Peche Island’s migratory birds.
Return to Riverside and rejoin the lively populace. Coventry Park is a popular destination for locals with its laid-back vibe and exhilarating summer concerts. In the Detroit River near the park, is the floating Windsor Peace Fountain. You won’t want to miss the nightly light show at this water fountain when you fly to Windsor from Chicago.
Fly from Chicago Midway International Airport (MDW) to Windsor International Airport (YQG), with a quick connection in Toronto. Chicago to Windsor flight time is 2 hours and 35 minutes on average. Connection times vary. The distance from Chicago to Windsor is around 1,035 km / 645 mi.
Enjoy complimentary drinks and snacks along the way.