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Not ready to book? to track prices.Find the cheapest flights from Canada to Chicago
Recent round-trip flight deals from Canada to Chicago
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Porter Airlines flights from Canada to Chicago Midway Airport
Our best Porter Airlines deals on Canada to Chicago Midway Airport flight tickets
WestJet flights from Canada to Chicago Midway Airport
Our best WestJet deals on Canada to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from Canada to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago Midway Airport?
The month of May is, on average, the cheapest month to fly to Chicago Midway Airport from Canada, with most prices found around $206. If you are unable to visit Chicago Midway Airport during the month of May, then departing from Canada during the month February is also very affordable. Most momondo users find prices during this month for around $213.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Monday is the cheapest day to fly to Chicago Midway Airport from Canada. The lowest ticket price found for a Monday departure recently was $246. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Thursday is the most expensive day to depart from Canada because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $275.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Canada in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $247 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $284. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Canada to Chicago Midway flight route?
Fly from Toronto Island to Chicago Midway for the best Canada - Chicago Midway flight prices
What cabin class options are available on Canada to Chicago Midway flights?
There are 4 cabin classes available to choose from on Canada to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Canada to Chicago Midway Airport flights?
No. A direct flight is the cheapest option for a flight between Canada to Chicago Midway Airport.
How many flights depart from Canada to Chicago Midway Airport on average per day?
As of June 2025, 3 flights take off from Canada and land in Chicago Midway Airport each day. The most common flight departure time for this route is 7:00AM, with 63% of daily flights taking off at noon.
How many flights depart from Canada to Chicago Midway Airport on average per week?
As of June 2025, there are 26 flights per week flying from Canada to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.
Cheap Canada to Chicago Midway Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Canada to Chicago Midway Airport
When did momondo last update prices for flights from Canada to Chicago Midway Airport?
Prices for flights from Canada to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from Canada to Chicago Midway Airport?
As of June 2025, there is 1 operator available to choose from for flights from Canada to Chicago Midway Airport.
How old do you have to be to fly from Canada to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Canada to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Canada to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Canada to Chicago Midway Airport is De Havilland (Bombardier) DHC-8-400 Dash 8Q (31.14% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (18.16%), Boeing 737-800 (14.61%), and Airbus A220-300 (10.21%).
Best airlines flying from Canada to Chicago Midway Airport
Compare and see reviews for airlines that fly from Canada to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $169 | Free Cancellation | Rating 8.0 288 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Canada to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Canada.
Can I find flights from Canada to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Canada with this policy.
How can momondo help me find flights from Canada to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Canada.
I’m not ready to book a flight from Canada to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Canada to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.