Cheap flights from Canada to Midway

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Boston (BOS)
Chicago (MDW)
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How to find the cheapest flight from
Canada to Midway (MDW)

All the information you need to plan the best null to MDW flight in 2021: compare Canada to Midway flight prices with the expected peak season, weather and rainfall in Midway.
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 34 days in advance to save up to 86% 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 34 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$ 428, or C$ 580 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 January. For low rates, April can be a great choice for travel to Chicago Midway Airport. Flights to Chicago Midway Airport from Canada in April are about C$ 312 on average during April, but can be found for as low as C$ 236.

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 October, November 2021

The best prices found for Canada to MDW flights for October, November
11 Nov - 14 Nov
C$ 241pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
11 Nov - 15 Nov
C$ 242pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
16 Nov - 18 Nov
C$ 244pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Canada to Midway 2021 flight deals

Cheap flights to Midway from Canada found for this year
11 Nov - 14 Nov
C$ 241pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
11 Nov - 15 Nov
C$ 242pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
16 Nov - 18 Nov
C$ 244pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Direct flights to Midway from Canada

Save time with Canada to Midway direct flight deals
11 Nov - 14 Nov
C$ 241pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
11 Nov - 15 Nov
C$ 242pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
16 Nov - 18 Nov
C$ 244pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Last minute flights from Canada to Midway

Late deals on round-trip flights to Midway from Canada, departing today and this week
30 Oct - 13 Nov
C$ 358pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
29 Oct - 5 Nov
C$ 438pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
28 Oct - 2 Nov
C$ 439pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

One-way flights to Midway from Canada

The cheapest one-way flights from Canada to Midway
1:00 a.m. - 9:16 a.m.
Multiple Airlines
2 stops
31h 16m
YEG - MDW
Multiple Airlines
C$ 217
FlightNetwork
1:35 a.m. - 6:58 a.m.
Delta
1 stop
6h 23m
YYZ - MDW
Delta
C$ 218
Delta
5:15 a.m. - 6:05 a.m.
Porter Airlines
Direct
1h 50m
YTZ - MDW
Porter Airlines
C$ 221
AirfareAssist

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Canada</span> to <span class="emphasized">Midway</span> flights.

Flight FAQs

From Canada to Midway

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$ 241, but on average you can expect to pay C$ 262.

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$ 263.

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 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: Air Canada, Delta or Porter Airlines.

What are the cheapest flights from Canada to Chicago Midway Airport?

The cheapest flight price from Canada to Chicago Midway Airport is C$ 258. On average you can expect to pay C$ 421. The most popular route, (Toronto Island - Chicago Midway), can usually be booked for C$ 242.

What are the most popular routes from Canada to Chicago Midway Airport?

While some choose either Montreal Pierre Elliott Trudeau Intl - Chicago Midway or Toronto Pearson Intl - Chicago Midway, Toronto Island - Chicago Midway is the most popular route from Canada to Chicago Midway Airport.

Related searches

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Rent a Car

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COVID Restrictions

View COVID Travel Restrictions for Midway (MDW)

Do I need a COVID test to fly to Midway from Canada?

Information is based on travel restrictions from Canada to Chicago Midway

Most visitors from Canada need to provide a negative COVID-19 test result and/or quarantine to enter Chicago Midway.

COVID-19 testing requirements
Visitors from Canada must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago Midway.

Quarantine requirements
Visitors from Canada are not required to quarantine after entering Chicago Midway.

Do I need a test to fly back to Canada from Midway?

Returning to Canada from Chicago Midway

COVID-19 testing requirements
Visitors from Chicago Midway must present a negative RT-PCR (NAAT) test taken 72 hours before departing to Canada.

Quarantine requirements
Visitors from Chicago Midway are not required to quarantine after entering Canada.

Hide COVID Travel Restrictions for Midway (MDW)

Departure points for flights from Canada to Midway

Select to see more specific information for flights to Midway from all departure points in Canada.

Destination information for Midway

Things to know before you go - useful duration and weather info for your trip from Canada to Midway.
Today's exchange rate
C$ 1 = $0.82
Flight duration from Canada to Chicago Midway
1h 43m
Average temperature for October in Midway
18.0 °C
Avg rainfall for October in Midway
66.0 mm

Airports servicing Chicago

Top 4 airlines flying from Canada to Chicago 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.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Porter Airlines
C$ 245 C$ 368 No cancel fee 52%
Search Porter Airlines flights
Delta
C$ 258 C$ 534 No cancel fee N/A
Search Delta flights
WestJet
C$ 259 C$ 473 No cancel fee 60%
Search WestJet flights
Air Canada
C$ 273 C$ 370 No cancel fee 67%
Search Air Canada flights
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