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Not ready to book? to track prices.Find the cheapest flights from Canada to Chicago Midway Airport
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Flights to Chicago Midway Airport - Travel Insights & Trends
Get data-powered insights and trends for flights to Chicago Midway Airport to help you craft the best travel plan.
What cabin class options are available on Canada to Chicago Midway flights?
There are 1 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.
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$ 321. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday 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$ 358.
What is the cheapest month to fly to Chicago Midway Airport?
In general, May 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$ 280. 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 C$ 289.
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$ 328. In contrast, the most expensive time of day to depart to Chicago Midway Airport is at noon when prices are around C$ 563.
How long does it take to fly to Chicago Midway Airport?
Flight times from Canada to Chicago Midway Airport vary, but if you’re flying out of Toronto Pearson Intl and flying into Chicago O'Hare Intl (one of the most popular routes), then the duration is 1h 54m on average. Another popular route from Canada to Chicago Midway Airport is flying from Vancouver Intl to Chicago O'Hare Intl, which will take roughly 4h 03m. Keep in mind that layovers or delays could extend your travel time.
How many flights depart from Canada to Chicago Midway Airport on average per day?
As of June 2025, there are 3 flights per day flying from Canada to Chicago Midway Airport. The most common time of day flights depart is 7:00a.m., with 63% of flights taking off at noon.
Cheapest flights to Chicago Midway
Find the cheapest flights to Chicago Midway from your nearest city or airport
| CHEAPEST MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORT | February | 31% cheaper | Flying from Toronto Pearson Intl Airport to Chicago Midway Airport costs on average just C$ 297 in February |
| MOST EXPENSIVE MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORT | August | 30% more expensive | It costs about C$ 557 for flights to Chicago Midway Airport from Toronto Pearson Intl Airport in August |
| MOST POPULAR MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORT | August | 500% more users visited | More momondo users searched in flights to Chicago Midway Airport from Toronto Pearson Intl Airport in August than any other month |
Cheap Chicago Midway Airport flight deals and tips
Summary info about Chicago Midway Airport flight prices, duration and airlines
Best One-Way Price | C$ 134 |
|---|---|
Best Round-Trip Price | C$ 215 |
Fastest flight time | 1h 49m |
Popular in | October |
Frequently asked questions about flying to Chicago Midway Airport
What is the cheapest month to fly to Chicago Midway Airport?
In general, when booking your flight to Chicago Midway Airport, May is the cheapest month on average.
How far in advance should I book a flight to Chicago Midway Airport?
From most locations, to find the best deals on airfare, our data shows that users booking 34 days before flying found the cheapest flight to Chicago Midway Airport.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
On average, the cheapest flights to Chicago Midway Airport are found when departing on a Wednesday. Try to avoid departing on a Sunday, as this is usually the most expensive day.
What is the cheapest time of day to fly to Chicago Midway Airport?
Generally, when visiting Chicago Midway Airport, Morning flights represent the best value. Noon flights are likely to have higher prices.
Is there an alternative airport near Chicago Midway Airport?
Finding an alternative and possibly cheaper destination airport near Chicago Midway Airport is possible. If you are planning a flight to Chicago Midway Airport, consider booking flights to Chicago O'Hare Intl Airport (26 km from Chicago city centre) or Chicago Greater Rockford Airport (126 km from Chicago city centre).
Is there a cheaper alternative to flying into Chicago?
You can find deals at Chicago O'Hare Intl Airport for C$ 1,062 on average, but that price can change based on your departure airport. To save money, try momondo’s Airport-to-Airport Pricing Tool.
What is the absolute cheapest flight to Chicago?
Users booking trips to Chicago from Nashville found flights 88% cheaper than the average price of flights to Chicago. To find the cheapest price to Chicago from your area, use momondo’s Airport-to-Airport Pricing Tool.
Which airlines fly to Chicago Midway Airport?
Porter Airlines, Air Transat and WestJet are the top three most popular airlines that fly to Chicago Midway Airport according to our data. Porter Airlines is the first choice among our users, with 93% of people opting to fly with this airline when travelling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
When did momondo last update prices for flights to Chicago Midway Airport?
Prices for flights to Chicago Midway Airport are updated daily.
How many operators does momondo search for flights to Chicago Midway Airport?
The number of operators available for flights to Chicago Midway Airport is 3 as of June 2025.
How old do you have to be to fly 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 to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
Travelling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights to Chicago. Millions of users trust and use momondo every year so you are in good company.
Can I find flights to Chicago with flexible booking policies on momondo?
All flight searches to Chicago on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights to Chicago?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight to Chicago.
I’m not ready to book a flight to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.
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Popular Flights to Chicago Midway Airport
Popular routes according to searches in the past day on momondo
Cheapest flight routes to Chicago Midway
These routes have the cheapest flights to Chicago Midway found by momondo users in Canada
| Departing | Destination | Best Time | Best Price |
|---|---|---|---|
| Toronto | Chicago | 1h 49m | C$ 215 |
| Montreal | Chicago | 4h 14m | C$ 287 |
| Winnipeg | Chicago | 4h 55m | C$ 334 |
| Ottawa | Chicago | 4h 49m | C$ 357 |
| Edmonton | Chicago | 7h 22m | C$ 363 |
| Vancouver | Chicago | 8h 41m | C$ 413 |
| Québec City | Chicago | 6h 24m | C$ 489 |
| Calgary | Chicago | 11h 10m | C$ 493 |
| Halifax | Chicago | 6h 49m | C$ 516 |
| Kelowna | Chicago | 13h 50m | C$ 532 |
| Saskatoon | Chicago | 11h 40m | C$ 665 |
| Regina | Chicago | 6h 25m | C$ 682 |
| Victoria | Chicago | 24h 47m | C$ 892 |
| Comox | Chicago | 12h 41m | C$ 938 |
| Grande Prairie | Chicago | 9h 39m | C$ 940 |
| Saint John | Chicago | 27h 39m | C$ 956 |