Cheap flights from Canada to Chicago Midway Airport
How far in advance should I book a flight from Canada to Chicago Midway Airport?
Travellers have found it’s best to book a flight 56 days in advance to save up to 45% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 56 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Canada to Chicago Midway Airport 1-2 weeks in advance for as low as C$ 395, or C$ 484 for flights within the next 24 hours.
What is the cheapest month to fly from Canada to Chicago Midway Airport?
Due to multiple factors, expect to potentially pay more when booking in December. For low rates, June can be a great choice for travel to Chicago Midway Airport. Flights to Chicago Midway Airport from Canada in June are about C$ 357 on average during June, but can be found for as low as C$ 217.
When is the cheapest time to fly from Canada to Chicago Midway Airport (CA - MDW)?
When flying from Canada to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Cheap flights from Canada to Midway in November, December 2022
The best prices found for Canada to MDW flights for November, December
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Canada to Midway 2022 flight deals
Cheap flights to Midway from Canada found for this year
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Cheap Delta flights from Canada to Midway
Toronto Pearson Intl
Chicago Midway
1 stop
7h 28mChicago Midway
Toronto Pearson Intl
1 stop
7h 50mDelta
Toronto Pearson Intl
Chicago Midway
1 stop
4h 01mChicago Midway
Toronto Pearson Intl
1 stop
7h 50mDelta
Toronto Pearson Intl
Chicago Midway
1 stop
7h 58mChicago Midway
Toronto Pearson Intl
1 stop
4h 35mDelta
Cheap Porter Airlines flights from Canada to Midway
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Direct flights to Midway from Canada
Save time with Canada to Midway direct flight deals
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 47mChicago Midway
Toronto Island
Nonstop
1h 42mPorter Airlines
Last minute flights from Canada to Midway
Late deals on round-trip flights to Midway from Canada, departing today and this week
Toronto Pearson Intl
Chicago Midway
1 stop
4h 01mChicago Midway
Toronto Pearson Intl
1 stop
7h 30mDelta
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Toronto Pearson Intl
Chicago Midway
1 stop
4h 01mChicago Midway
Toronto Pearson Intl
1 stop
3h 38mDelta
One-way flights to Midway from Canada
The cheapest one-way flights from Canada to Midway
Toronto Island
Chicago Midway
Nonstop
1h 50mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mPorter Airlines
Related info for your journey
Useful info, stats and facts about Canada to Midway flights.
Which airlines flying from Canada to Chicago Midway have flexible cancellations due to COVID-19?
Porter Airlines, Delta, and WestJet are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.
Can I find flights from Canada to Chicago Midway Airport for under C$ 300 on Cheapflights?
Yes, there are multiple flights from Canada to Chicago Midway Airport for under C$ 300. The cheapest flight booked recently is on Porter Airlines for just C$ 221, but on average you can expect to pay C$ 243.
Are there direct flights from Canada to Chicago Midway Airport for under C$ 300 on Cheapflights?
Cheapflights has 20 direct flights from Canada to Chicago Midway Airport under C$ 300. A good price for a direct flight from Canada to Chicago Midway Airport is less than C$ 241.
Are there last-minute flights available from Canada to Chicago Midway Airport for under C$ 400?
There are currently 20+ open flights from Canada to Chicago Midway Airport within the next 7 days for less than C$ 400.
What are the most popular routes from Canada to Chicago Midway Airport?
While some choose either Toronto Island - Chicago Midway or Toronto Pearson Intl - Chicago Midway, Montreal Pierre Elliott Trudeau Intl - Chicago Midway is the most popular route from Canada to Chicago Midway Airport.
What are the most popular airlines that fly from Canada to Chicago Midway Airport?
Before booking your flight from Canada to Chicago Midway Airport check out the most popular airlines for this route: Endeavor Airlines, Air Canada or Delta.
What are the cheapest flights from Canada to Chicago Midway Airport?
The cheapest flight price from Canada to Chicago Midway Airport is C$ 261. On average you can expect to pay C$ 261. The most popular route, (Montreal Pierre Elliott Trudeau Intl - Chicago Midway), can usually be booked for C$ 277.
Flights to Midway from Canada
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Departure points for flights from Canada to Midway
Select to see more specific information for flights to Midway from all departure points in Canada
Top 3 airlines flying from Canada to Midway
The chart below displays the airlines Cheapflights users travelling from Canada to Midway choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Hourly flight availability from Canada to Midway
See what time of day planes typically take off from Canada to Midway
| 1%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 31%of flight departures | Morning6 am to noon |
| 68%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |