What is the cheapest airline that flies from Chicago Midway to Canada?

Delta is the most popular carrier operating from Chicago Midway to Canada

What is the most punctual flight time for Chicago to Canada flights?

Generally, flights departing in the evening tend to experience fewer delays. Flights departing at night have, in the past, seen delays more frequently in comparison.

Which airline has the best punctuality record on Chicago to Canada flights?

According to our data, Porter Airlines has had the least delays on this route over the last 12 months, with about 17% of their flights experiencing any sort of delay.

How often are flights from Chicago to Canada delayed?

Historically, on average around 18% of flights between Chicago and Canada have experienced a delay on any given week. The average delay length over the past 12 months has been 111 minutes.

What day of the week experiences the fewest flight delays on this route?

Saturday is statistically the day of the week that experiences the fewest delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

When did momondo last update prices for flights from Chicago Midway Airport to Canada?

Prices for flights from Chicago Midway Airport to Canada were last updated today.

How old do you have to be to fly from Chicago Midway Airport to Canada?

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 Chicago Midway Airport to Canada.

What documentation or ID do you need to fly to Canada?

The necessary travel and health documents for your Canada 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.

C$ 191 Cheap Flights from Chicago Midway Airport to Canada in 2026/27

Find the cheapest flights from Chicago Midway Airport to Canada

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:37 a.m. - 5:20 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

6h 43m1 stop Detroit Metropolitan Wayne County

2:25 p.m. - 6:01 p.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

4h 36m1 stop Detroit Metropolitan Wayne County

C$ 565Delta

Thu, 3 Dec - Sun, 6 Dec

9:29 a.m. - 3:14 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

4h 45m1 stop Detroit Metropolitan Wayne County

6:10 a.m. - 8:49 a.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

3h 39m1 stop Detroit Metropolitan Wayne County

C$ 565Delta

Tue, 22 Dec - Tue, 29 Dec

9:37 a.m. - 5:20 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

6h 43m1 stop Detroit Metropolitan Wayne County

2:25 p.m. - 6:01 p.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

4h 36m1 stop Detroit Metropolitan Wayne County

C$ 566Delta

Thu, 3 Dec - Sun, 6 Dec

6:41 p.m. - 11:07 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

3h 26m1 stop Detroit Metropolitan Wayne County

2:25 p.m. - 6:01 p.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

4h 36m1 stop Detroit Metropolitan Wayne County

C$ 568Air France

Thu, 3 Dec - Sun, 6 Dec

9:37 a.m. - 5:20 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

6h 43m1 stop Detroit Metropolitan Wayne County

2:25 p.m. - 6:01 p.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

4h 36m1 stop Detroit Metropolitan Wayne County

C$ 568Delta

Thu, 3 Dec - Sun, 6 Dec

6:41 p.m. - 11:07 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

3h 26m1 stop Detroit Metropolitan Wayne County

6:00 a.m. - 9:37 a.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

4h 37m1 stop Detroit Metropolitan Wayne County

C$ 576Delta

Sat, 12 Dec - Mon, 14 Dec

1:59 p.m. - 7:14 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

4h 15m1 stop Detroit Metropolitan Wayne County

9:45 a.m. - 1:01 p.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

4h 16m1 stop Detroit Metropolitan Wayne County

C$ 576Delta

Wed, 13 Jan - Tue, 19 Jan

1:41 p.m. - 11:07 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

8h 26m1 stop Detroit Metropolitan Wayne County

2:25 p.m. - 6:01 p.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

4h 36m1 stop Detroit Metropolitan Wayne County

C$ 576Delta

Fri, 11 Dec - Tue, 15 Dec

9:38 a.m. - 4:19 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

5h 41m1 stop Detroit Metropolitan Wayne County

9:45 a.m. - 1:01 p.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

4h 16m1 stop Detroit Metropolitan Wayne County

C$ 576Delta

Wed, 13 Jan - Thu, 18 Feb

5:30 p.m. - 11:41 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 11m1 stop Minneapolis St Paul

7:00 a.m. - 12:04 p.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

6h 04m1 stop Atlanta Hartsfield-Jackson

C$ 582Delta

Sat, 12 Dec - Sun, 13 Dec

Cheap last-minute flights

Enter your travel dates to find the best prices.

6:42 p.m. - 1:40 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

17h 58m2 stops Atlanta Hartsfield-Jackson Orlando

9:35 a.m. - 7:47 p.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

11h 12m1 stop Orlando

C$ 780Multiple Airlines

Wed, 11 Nov - Wed, 25 Nov

9:30 a.m. - 1:30 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

3h 00m1 stop Detroit Metropolitan Wayne County

9:45 a.m. - 12:51 p.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

4h 06m1 stop Detroit Metropolitan Wayne County

C$ 808Delta

Tue, 10 Nov - Tue, 24 Nov

6:00 a.m. - 4:15 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

9h 15m1 stop Atlanta Hartsfield-Jackson

12:15 p.m. - 6:04 p.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

6h 49m1 stop Detroit Metropolitan Wayne County

C$ 808Delta

Wed, 11 Nov - Wed, 25 Nov

9:30 a.m. - 5:20 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

6h 50m1 stop Detroit Metropolitan Wayne County

6:00 a.m. - 11:25 a.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

6h 25m1 stop Detroit Metropolitan Wayne County

C$ 808Delta

Wed, 11 Nov - Thu, 26 Nov

5:13 p.m. - 11:57 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

5h 44m1 stop Atlanta Hartsfield-Jackson

12:15 p.m. - 6:04 p.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

6h 49m1 stop Detroit Metropolitan Wayne County

C$ 808Delta

Tue, 10 Nov - Wed, 25 Nov

9:30 a.m. - 1:30 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

3h 00m1 stop Detroit Metropolitan Wayne County

6:00 a.m. - 11:25 a.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

6h 25m1 stop Detroit Metropolitan Wayne County

C$ 808Delta

Tue, 10 Nov - Thu, 26 Nov

1:05 p.m. - 9:57 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

7h 52m1 stop Atlanta Hartsfield-Jackson

6:00 a.m. - 9:46 a.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

4h 46m1 stop Detroit Metropolitan Wayne County

C$ 808Delta

Wed, 11 Nov - Tue, 24 Nov

5:29 p.m. - 11:30 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 01m1 stop Minneapolis St Paul

6:00 a.m. - 9:46 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

4h 46m1 stop Detroit Metropolitan Wayne County

C$ 812Delta

Sat, 14 Nov - Wed, 25 Nov

6:44 p.m. - 11:27 p.m.MDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

3h 43m1 stop Detroit Metropolitan Wayne County

6:00 a.m. - 11:25 a.m.YUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

6h 25m1 stop Detroit Metropolitan Wayne County

C$ 812Delta

Sat, 14 Nov - Thu, 26 Nov

9:30 a.m. - 5:20 p.m.MDW Chicago Midway-YYZ Toronto Pearson Intl

6h 50m1 stop Detroit Metropolitan Wayne County

6:00 a.m. - 11:25 a.m.YYZ Toronto Pearson Intl-MDW Chicago Midway

6h 25m1 stop Detroit Metropolitan Wayne County

C$ 822Delta

Wed, 11 Nov - Thu, 26 Nov

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Delta flights from Chicago Midway Airport to Canada

Our best Delta deals on Chicago Midway Airport to Canada flight tickets

Delta

3 Dec

MDW9:37 a.m.Chicago Midway

6h 43m

1 stop

YYZ5:20 p.m.Toronto Pearson Intl

6 Dec

YYZ2:25 p.m.Toronto Pearson Intl

4h 36m

1 stop

MDW6:01 p.m.Chicago Midway

C$ 565

Delta

3 Dec

MDW9:37 a.m.Chicago Midway

6h 43m

1 stop

YYZ5:20 p.m.Toronto Pearson Intl

6 Dec

YYZ2:25 p.m.Toronto Pearson Intl

4h 36m

1 stop

MDW6:01 p.m.Chicago Midway

C$ 566

Delta

3 Dec

MDW9:37 a.m.Chicago Midway

6h 43m

1 stop

YYZ5:20 p.m.Toronto Pearson Intl

6 Dec

YYZ2:25 p.m.Toronto Pearson Intl

4h 36m

1 stop

MDW6:01 p.m.Chicago Midway

C$ 568

JetBlue flights from Chicago Midway Airport to Canada

Our best JetBlue deals on Chicago Midway Airport to Canada flight tickets

JetBlue

5 Dec

MDW6:47 p.m.Chicago Midway

3h 26m

1 stop

YYZ11:13 p.m.Toronto Pearson Intl

15 Dec

YYZ6:06 a.m.Toronto Pearson Intl

8h 01m

1 stop

MDW1:07 p.m.Chicago Midway

C$ 622

JetBlue

10 Dec

MDW1:08 p.m.Chicago Midway

9h 46m

1 stop

YUL11:54 p.m.Montreal Pierre Elliott Trudeau Intl

13 Dec

YUL7:06 a.m.Montreal Pierre Elliott Trudeau Intl

10h 16m

1 stop

MDW4:22 p.m.Chicago Midway

C$ 646

JetBlue

9 Dec

MDW1:47 p.m.Chicago Midway

8h 26m

1 stop

YYZ11:13 p.m.Toronto Pearson Intl

11 Jan

YYZ12:16 p.m.Toronto Pearson Intl

6h 50m

1 stop

MDW6:06 p.m.Chicago Midway

C$ 664

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Canada that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Thu 3/12

9:37 a.m.-5:20 p.m.

1 stop6h 43m

Toronto Pearson Intl

Sun 6/12

2:25 p.m.-6:01 p.m.

1 stop4h 36m

C$ 565

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Tue 22/12

9:29 a.m.-3:14 p.m.

1 stop4h 45m

Toronto Pearson Intl

Tue 29/12

6:10 a.m.-8:49 a.m.

1 stop3h 39m

C$ 565

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Thu 3/12

9:37 a.m.-5:20 p.m.

1 stop6h 43m

Toronto Pearson Intl

Sun 6/12

2:25 p.m.-6:01 p.m.

1 stop4h 36m

C$ 566

Quickest round-trip

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Thu 3/12

6:41 p.m.-11:07 p.m.

1 stop3h 26m

Toronto Pearson Intl

Sun 6/12

2:25 p.m.-6:01 p.m.

1 stop4h 36m

C$ 568

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Thu 3/12

9:37 a.m.-5:20 p.m.

1 stop6h 43m

Toronto Pearson Intl

Sun 6/12

2:25 p.m.-6:01 p.m.

1 stop4h 36m

C$ 568

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Sat 12/12

6:41 p.m.-11:07 p.m.

1 stop3h 26m

Toronto Pearson Intl

Mon 14/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

C$ 576

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Wed 13/1

1:59 p.m.-7:14 p.m.

1 stop4h 15m

Toronto Pearson Intl

Tue 19/1

9:45 a.m.-1:01 p.m.

1 stop4h 16m

C$ 576

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Fri 11/12

1:41 p.m.-11:07 p.m.

1 stop8h 26m

Toronto Pearson Intl

Tue 15/12

2:25 p.m.-6:01 p.m.

1 stop4h 36m

C$ 576

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Wed 13/1

9:38 a.m.-4:19 p.m.

1 stop5h 41m

Toronto Pearson Intl

Thu 18/2

9:45 a.m.-1:01 p.m.

1 stop4h 16m

C$ 576

ChicagoMontreal

MDW Chicago Midway - YUL Montreal Pierre Elliott Trudeau Intl

MDWYUL

Chicago Midway

Sat 12/12

5:30 p.m.-11:41 p.m.

1 stop5h 11m

Montreal Pierre Elliott Trudeau Intl

Sun 13/12

7:00 a.m.-12:04 p.m.

1 stop6h 04m

C$ 582

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to Canada

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

Prices

Airlines

Delays

What is the cheapest month to fly to Canada?

In general, January is the cheapest month to fly from Chicago Midway Airport to Canada. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 290. If you’re not able to fly to Canada in January, then April is your next best option. Flight prices from Chicago Midway Airport to Canada during April average around C$ 322.

What is the cheapest day to depart on your flight to Canada?

Our data shows that Thursday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as C$ 343. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 761. These prices are subject to change though, so be sure to set up a Price Alert for flights to Canada.

What is the cheapest time of day to depart on your flight to Canada?

According to our data, the cheapest time of day to fly to Canada is in the morning. momondo users have found flights departing from Chicago Midway Airport to Canada in the morning for as low as C$ 429. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the afternoon is when there is more demand to fly to Canada, so prices are often more expensive at around C$ 459 per ticket.

What is the cheapest Chicago Midway to Canada flight route?

Fly from Chicago Midway to Toronto Island for the best Chicago Midway - Canada flight prices

What cabin class options are available on Chicago Midway Airport to Canada flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport to Canada 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 Chicago Midway Airport to Canada flights?

You could potentially save up to 15% on your flight if you consider stops on a Chicago Midway Airport to Canada flight.

Cheap Chicago Midway Airport to Canada flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Canada

Best price found	C$ 191
Fastest flight time	3h 13m
Direct flights	None

The best one-way flight to Canada from Chicago Midway Airport in the past 72 hours is C$ 191. The best round-trip flight deal from Chicago Midway Airport to Canada found on momondo in the last 72 hours is C$ 565.

The fastest flight from Chicago Midway Airport to Canada takes 3h 13m

There are no direct flights from Chicago Midway Airport to Canada. There are no popular flight routes from Chicago Midway Airport to Canada.

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Canada

When did momondo last update prices for flights from Chicago Midway Airport to Canada?
Prices for flights from Chicago Midway Airport to Canada were last updated today.
How old do you have to be to fly from Chicago Midway Airport to Canada?
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 Chicago Midway Airport to Canada.
What documentation or ID do you need to fly to Canada?
The necessary travel and health documents for your Canada 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.
What is the most popular plane model from Chicago Midway Airport to Canada?
Based on momondo bookings for flights between Chicago Midway Airport and Canada, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 40.35% of the total bookings. Other popular models include Embraer 175 with 11.29%, Embraer 175 (Enhanced Winglets) with 9.65%, and Embraer 170 with 7.02%.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Canada?

It is quick and easy to find Chicago to Canada flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Canada that suits you.

Can I find flights from Chicago to Canada with flexible booking policies on momondo?

All flight searches from Chicago to Canada on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Canada?

Once all potential Chicago to Canada flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Canada right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Canada 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.