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Recent round-trip flight deals from Canada to Chicago
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Air Transat flights from Canada to Chicago Midway Airport
Our best Air Transat 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?
In general, February is the cheapest month to fly from Canada to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 296. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Canada during the month July is also very affordable. Most momondo users find prices during this month for around C$ 323.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
The cheapest day to depart on your flight to Chicago Midway Airport is on a Wednesday when prices can be found for as low as C$ 338. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday is the most expensive day to depart from Canada because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 366.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Our most recent data shows that the best time of day to fly to Chicago Midway Airport is in the morning. Flights from Canada to Chicago Midway Airport during this time can be as low as C$ 350. In contrast, the most expensive time of day to depart to Chicago Midway Airport is at noon when prices are around C$ 576.
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
How many flights depart from Canada to Chicago Midway Airport on average per day?
As of April 2025, there are 3 flights per day flying from Canada to Chicago Midway Airport. The most common time of day flights depart is 3:00p.m., with 50% of flights taking off at noon.
How many flights depart from Canada to Chicago Midway Airport on average per week?
As of April 2025, 24 flights take off from Canada and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 17% of weekly 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 are updated daily.
How many operators does momondo search for flights from Canada to Chicago Midway Airport?
As of April 2025, there are 2 operators 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?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify 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 flights between Canada and Chicago Midway Airport, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 29.14% of the total bookings. Other popular models include Boeing 737 MAX 8 with 13.78%, Embraer 175 (Enhanced Winglets) with 13.47%, and Airbus A220-300 with 9.93%.
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 C$ 261 | Free Cancellation | Rating 8.0 281 reviews | |||
| PriceFrom C$ 479 | Free Cancellation | Rating 7.2 2,809 reviews |
Travelling 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?
All flight searches from Canada to Chicago on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Canada to Chicago?
Once you have performed a search for Canada to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Canada to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Canada. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.