
Windsor to Chicago Flight Tickets
Compare the best flight deals from Windsor to Chicago
About Windsor - Chicago Flights
Find the best prices for flights between Windsor (Canada) and Chicago (United States) on Tripuck. We compare prices from hundreds of airlines to offer you the best options.
Windsor has 1 airports, while Chicago has 6 airports. Compare flights between all airports to find the best deal.
Cheapest Months for Windsor - Chicago Flights
Best month to fly
November 2026 - 19.663 ₺
November 2026
19.663 ₺
1 stops
Cheapest| Ay | Flight Type | Price |
|---|---|---|
| November 2026Cheapest | 1 stops | 19.663 ₺ |
Prices may change. Based on recent searches.
Popular Windsor - Chicago Flights
Windsor - Chicago

Airlines on Windsor - Chicago Route
| Havayolu | Uçuş Tipi | Fiyat |
|---|---|---|
| 1 stops | 19.663 ₺ |
Windsor Airports
Chicago Airports
Alternative Routes
Windsor and Chicago - Airport Transportation
Windsor International Airport (YQG)
How to Get to the Airport
Bus: You can reach the airport by transferring to stops around the airport from the Downtown Transit Terminal and surrounding stops in Windsor city center using Transit Windsor buses. The travel time from the city center to the airport is approximately 25-40 minutes, followed by an additional 5-10 minutes of walking or a short drive. There are generally services every 20-30 minutes during the day.
Taxi: It is possible to reach the airport from Windsor city center by taxi. The taxi journey takes approximately 15-25 minutes, depending on traffic. Finding a taxi in the city center is quite easy.
Uber: Uber can also be preferred for transportation from Windsor city center to the airport. The travel time by Uber is approximately 15-25 minutes, depending on traffic conditions. You can easily request a vehicle through the app.
Car Rental: You can reach the airport by renting a car from car rental offices located in the city center. It is advisable to consider traffic conditions while traveling by car rental.
Metro/Train: NOT AVAILABLE There is no metro or train line from Windsor city center to Windsor International Airport. Therefore, road transportation should be preferred for reaching the airport from the city center.
Chicago Midway International Airport (MDW)
From Airport to City Center
Metro/Train: The CTA Orange Line station is located at the end of the enclosed pedestrian walkway connected to the terminal building. The train reaches the Loop area from MDW in approximately 25 minutes. The frequency of service varies depending on the time of day: generally every 3–15 minutes on weekdays, approximately every 10–15 minutes on Saturdays, and about every 10–15 minutes on Sundays and holidays. Operating hours from MDW to the Loop are weekdays 03:30–01:05, Saturdays 04:00–01:05, and Sundays and holidays 04:30–01:05.
Bus: There is no direct, regular, and fast CTA bus line between MDW and the city center; therefore, the Orange Line is generally preferred for transportation to the city center. The N62 Archer bus, which serves the airport, is an alternative CTA line that operates throughout the night; however, its route does not go directly to the Loop and may require a transfer. The frequency and hours of the N62 line may vary according to the schedule.
Taxi: Taxi services are available at the airport. The taxi stand is conveniently located outside the terminal building. Travel time may vary depending on traffic conditions, but generally, it takes 20-30 minutes to reach the city center. Taxi services operate 24 hours a day.
Uber/Bolt: App-based ride-hailing services like Uber and Bolt are also available at the airport. Vehicles you request through the app will be waiting for you in designated areas outside the airport terminal. Travel time and cost may vary depending on traffic conditions.
Car Rental: There are many car rental companies at the airport. You can prepare the necessary documents for rental and head to the car rental offices located within the terminal to rent the vehicle you want. Car rental services are generally open 24 hours.
O'Hare International Airport (ORD)
From Airport to City Center
Metro/Train: The CTA Blue Line Train is the most convenient option for transportation from O'Hare International Airport to downtown Chicago. The airport station is directly connected to Terminals 1, 2, and 3. Access from Terminal 5 is possible via a free shuttle train. The journey takes approximately 40-45 minutes. Services operate 24 hours a day, with trains running every 5-10 minutes during peak hours.
Bus (CTA and Private Shuttles): Buses connecting O'Hare Terminals 1, 2, 3, and 5 operate routes to downtown. The journey time varies between 45-60 minutes depending on traffic conditions. Services run every 15-30 minutes and generally operate from 5:00 AM to 11:45 PM.
Taxi: Official taxi stands at O'Hare are located at each terminal exit and provide direct transportation to downtown. The journey time varies between 30-60 minutes depending on traffic. Taxi services are available 24 hours a day.
Airport App-Based Rides (Uber/Lyft): Apps like Uber and Lyft operate in designated pickup areas at O'Hare. Journey time and cost can vary based on traffic and demand.
Car Rental: Various car rental companies are available at the airport. Car rental options can be arranged at offices located at terminal exits or at rental centers accessible via shuttle services.

