Cheap flights from Windsor to Chicago Midway

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 much is a flight from Windsor to Chicago Midway?

Prices vary based on date, airline, and availability. Compare several options if you're flying between Windsor and Chicago.

Pick a travel date to see today’s available fares.

Fares change often — checking several times throughout the week can make a big difference. Booking in advance often means access to lower prices for the Windsor - Chicago Midway route.

What are the airport options between Windsor and Chicago?

If both departure and destination cities offer multiple airports, comparing them can help you save time and money.

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

Some airports have different terminals for low-cost and traditional airlines — knowing in advance can save time. You can filter results to see only the airports that suit you.

Flights from Windsor to Chicago - Midway

Refine your flight search from Windsor to Chicago Midway

With Jetcost, it’s easy to narrow down results to find flights that match your schedule and preferences. You can filter by airline, price, trip type, and more — including offers from the best airlines and travel agencies.

Other popular destinations

Also looking at United States? These cities are trending: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Online agencies can show different offers for the same flight — it’s worth comparing. Filters let you narrow things down further, like selecting a specific time slot to find flights that suit you best.
Frequently Asked Questions

Frequently asked questions about flights from Windsor to Chicago Midway.

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

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

How far is Windsor from Chicago?

Windsor is about 399 km from Chicago.

What are the airports in Chicago?

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

What are the airports in Windsor?

Windsor has one airport: Windsor.

What are the most popular cities in United States?

The most popular cities in United States according to our users' searches are: Las Vegas, Los Angeles, Miami, New York City, Orlando.

When should I book a flight from Windsor to Chicago?

The best time to book a flight from Windsor to Chicago is 4 months in advance, while the worst time is 16 weeks in advance.

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

This information is not available at the moment.

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

This information is not available at the moment.

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

This information is not available at the moment.