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This Weekend's Flight Deals to Windsor

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fares from $177 One Way, $382 Round Trip from Chicago to Windsor

Prices starting at $382 for return flights and $177 for one-way flights to Windsor were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

More About Flying To Windsor from Chicago

Route Information for Flights from Chicago to Windsor

Origin Airport IATA CodeCHI
Destination Airport IATA CodeXCM
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Traveling from Chicago to Windsor

Airports in Chicago

The city of Chicago is primarily served by two international airports. Travelers looking for low-fare flights from Chicago can use Orbitz.com to find flights from both O'Hare and Midway. O'Hare International Airport is located approximately 17 miles northwest of downtown Chicago. Midway International Airport is located on the city's southwest side, approximately eight miles from Chicago's Loop. O'Hare serves as a hub for American Airlines and United Airlines, and Midway is a hub for Southwest Airlines.

Chicago Airport Parking

Daily, hourly, and valet parking are available at O'Hare. Rates vary from $2.00 to $10.00 per hour. An economy parking lot is also available at a rate of $2.00 per hour. Similar parking options and rates apply at Midway.

Chicago Airport Transportation

There are numerous transportation options for getting to and from both O'Hare and Midway. O'Hare can be accessed via regional trains, buses, and local mass transit lines. The CTA Blue Line offers a fast and convenient transportation option to and from this airport. Midway is served by the CTA Orange Line. Car rental services are available at both airports, and travelers can quickly book car rental services at either airport using Orbitz.com.

Chicago Airport Restaurants

Both O'Hare and Midway offer a variety of restaurant options for travelers. Restaurants located in both airports include Starbuck's Coffee, Chicago Style Hot Dogs, McDonald's, Auntie Anne's, Chili's, Cinnabon, and Dunkin Donuts, making it easy for visitors to grab a quick breakfast, snack, or meal. By using Orbitz.com, travelers can quickly and easily find low-fare flights from Chicago.

Windsor International Airport

Use the search tools on Orbitz.com to find cheap flights to Windsor, Ontario. Windsor International Airport (3200 County Road 42) is conveniently located about two miles from the center of Windsor. It is also within minutes of Detroit. Air Canada, Porter, WestJet and Sunwing fly into this airport, giving you a variety of travel options. This airport also offers a newly renovated lounge area and terminal-wide Wi-Fi.

Getting from Windsor International Airport

Veteran Cab provides taxi service from the airport, but you will need to call them to arrange a pickup. Windsor Essex Airport Limo Ltd. offers on-site limousine service. The City of Windsor Transit Authority features a fixed bus route to the airport on weekdays. Three car-rental companies, Avis, Budget and National, can be found a few meters away from the terminal building. You can arrange for a rental car online at Orbitz.com.

Weather in Windsor

Windsor is the warmest city in Ontario, with highs that reach the low 80s in July. December through March is the cold season, which has lows in the teens and highs in the low 30s. Light rain and light snow are the most common forms of precipitation in the city. Rain is most likely to occur in April or October, while snow is most common in January.

Attractions in Windsor

In the warm season, you can enjoy Windsor's scenery at popular tourist spots such as Coventry Gardens, Dieppe Gardens and Jackson Park. If you will be visiting in the colder months, you should check out traveler favorites like Caesars Windsor, Devonshire Mall and the Art Gallery of Windsor. Find cheap flights to Windsor today at Orbitz.com.

Flights from Chicago to Windsor - Frequently Asked Questions

What is the shortest flight from Chicago to Windsor?

It can take as little as 2 hours and 40 minutes to fly from Chicago, IL (MDW-Midway Intl.) to Windsor, ON (YQG). Buckle up and enjoy those window views, because you'll be touching down in next to no time.

If I am not able to travel due to COVID-19, can I cancel my flight to Windsor?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Windsor have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Windsor with flexible change policies?

In most cases you'll have the option to reschedule your flight to Windsor without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2019 shows that Tuesday is the cheapest day to depart, followed by Monday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a fresh start to the new year. Be aware that the most expensive time to fly isn't the height of summer, as most people assume, but the festive month of December.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2019 saved over 50% on their airfares. Get mixing and matching today!

*According to flight demand on Orbitz.com from January to December 2019. Savings are subject to change based on departure location, date and destination.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.