Cheap flights from Chicago to Windsor

Flights tailored to your budget

Selected dates may not give results due to COVID-19. We suggest you change the dates.
Multi-city Round trip One way
Round trip
One way
Multi-city
From
No results match your search criteria
To
No results match your search criteria
{{ weekDay }}
Dates
{{ panel.label }}
Looking for a one-way flight?

Flexible dates can save you money

Explore nearby dates to find lower fares

{{ fromDate | dateToLongNamedDate }}
?
Flexible dates
Depart {{ flexibleFromDateLabel }}
{{ option.label }}
?
Return {{ flexibleToDateLabel }}
{{ option.label }}
Passengers / Class
Number of passengers
Adults
{{ adults }}
Children
{{ children }}
Infants
{{ infants }}
Class
Economy
Available for Economy only
New Multi-city experience

Discover a new Multi-city search experience from Jetcost, designed to handle more complex itineraries. By continuing, you’ll be taken to a dedicated page powered by Kiwi.com.
How do we get the info you see here? Please note that we offer an online comparison service and that all information and prices regarding services and/or products available on our website are provided by our third-party partners. We do our best to show you up-to-date information, but please note that we are not responsible for the completeness or accuracy of the information published, so please check all conditions carefully on the website of the partner before making a booking. Please check our Terms and Conditions for more details. Read more

How to estimate the price of a flight from Chicago to Windsor?

It depends. Prices for flights from Chicago to Windsor fluctuate based on several factors.

Select your dates to check current offers.

Checking fares across several nearby dates can help you see which days offer the best deals. Jetcost lets you track price changes and grab the best opportunities.

Are there multiple airports in Chicago and Windsor?

If your departure or arrival city has more than one airport, it's worth comparing all of them for timing and pricing.

  • Airports in Chicago: 3 airports are active in Chicago - Midway, O'Hare, Rockford.
  • Airports in Windsor: Windsor is the only airport currently running.

If you're traveling with a group or bulky luggage, look into parking or transport options. Alternative airports may offer faster transfers or better rates.

Adjust your flight filters for Chicago – Windsor

Jetcost gives you tools to search smarter. Pick your ideal price range, airline, departure time, and flight type — then compare offers from the best travel agencies and carriers.

Other popular destinations

Planning a trip to Canada? These cities are popular too: Calgary, Halifax, Montreal, Toronto, Vancouver.

Sorting options let you see the most affordable flights first. Some results may include extra fees shown only at checkout — always read carefully to see what’s included.
Frequently Asked Questions

Frequently asked questions about flights from Chicago to Windsor.

How much does an airline ticket from Chicago to Windsor cost?

Flight prices can vary a lot depending on the period and destination. At the moment, this information is not available for flights from Chicago to Windsor.

How far is Chicago from Windsor?

Chicago is about 393 km from Windsor.

What are the airports in Windsor?

Windsor has one airport: Windsor.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the most popular cities in Canada?

The most popular cities in Canada according to our users' searches are: Calgary, Halifax, Montreal, Toronto, Vancouver.

When should I book a flight from Chicago to Windsor?

The best time to book a flight from Chicago to Windsor is 1 month in advance, while the worst time is 1 week in advance.

What is the cheapest month to fly from Chicago to Windsor?

This information is not available at the moment.

What is the most expensive month to fly from Chicago to Windsor?

This information is not available at the moment.

What is the best day of the week to fly from Chicago to Windsor?

This information is not available at the moment.