Flights from Chicago to Windsor

Where history is always brewing

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.

Where Windsor’s waterfront shines

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.