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

Porter Airlines, Delta, and Air Transat are the most popular carriers operating from Chicago Midway to Canada

How often are flights from Chicago to Canada delayed?

Historically, on average around 15% 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 115 minutes.

How many flights depart from Chicago Midway Airport to Canada on average per week?

22 flights are operational weekly from Chicago Midway Airport to Canada as of June 2026. The most popular departure day for this route is Mon, with 18% of flights per week taking off on this day.

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 14% of their flights experiencing any sort of delay.

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

Thursday 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.

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.

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$ 135 Cheap Flights from Chicago Midway Airport to Canada in 2026

Find the cheapest flights from Chicago Midway Airport to Canada

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:25 a.m. - 1:05 p.m.

MDW

YTZ

1h 40mdirect

8:50 a.m. - 9:40 a.m.

YTZ

MDW

1h 50mdirect

C$ 302Porter Airlines

Tue, 14 Jul - Wed, 15 Jul

3:20 p.m. - 6:00 p.m.

MDW

YTZ

1h 40mdirect

8:50 a.m. - 9:40 a.m.

YTZ

MDW

1h 50mdirect

C$ 304Porter Airlines

Thu, 25 Jun - Mon, 29 Jun

10:25 a.m. - 1:05 p.m.

MDW

YTZ

1h 40mdirect

8:50 a.m. - 9:40 a.m.

YTZ

MDW

1h 50mdirect

C$ 305Porter Airlines

Sat, 27 Jun - Mon, 29 Jun

3:20 p.m. - 6:00 p.m.

MDW

YTZ

1h 40mdirect

8:50 a.m. - 9:40 a.m.

YTZ

MDW

1h 50mdirect

C$ 308Porter Airlines

Fri, 17 Jul - Tue, 21 Jul

10:25 a.m. - 1:05 p.m.

MDW

YTZ

1h 40mdirect

8:50 a.m. - 9:40 a.m.

YTZ

MDW

1h 50mdirect

C$ 309Porter Airlines

Mon, 29 Jun - Tue, 21 Jul

9:30 a.m. - 3:18 p.m.

MDW

YYZ

4h 48m

1 stop

9:45 a.m. - 12:34 p.m.

YYZ

MDW

3h 49m

1 stop

C$ 380Delta

Sat, 12 Sep - Sat, 19 Sep

9:24 a.m. - 5:24 p.m.

MDW

YYZ

7h 00m

1 stop

6:10 a.m. - 9:17 a.m.

YYZ

MDW

4h 07m

1 stop

C$ 392Delta

Tue, 1 Sep - Sun, 6 Sep

9:19 a.m. - 3:20 p.m.

MDW

YYZ

5h 01m

1 stop

12:09 p.m. - 6:07 p.m.

YYZ

MDW

6h 58m

1 stop

C$ 401KLM

Sat, 25 Jul - Sat, 1 Aug

10:25 a.m. - 8:40 a.m.

MDW

YWG

22h 15m

1 stop

8:10 p.m. - 9:40 a.m.

YWG

MDW

13h 30m

1 stop

C$ 564Multiple Airlines

Thu, 25 Jun - Mon, 29 Jun

10:25 a.m. - 11:22 p.m.

MDW

YHZ

10h 57m

1 stop

11:00 p.m. - 9:40 a.m.

YHZ

MDW

12h 40m

1 stop

C$ 577Multiple Airlines

Fri, 3 Jul - Sat, 11 Jul

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KLM flights from Chicago Midway Airport to Canada

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

KLM

25 Jul

MDW9:19 a.m.Chicago Midway

5h 01m

1 stop

YYZ3:20 p.m.Toronto Pearson Intl

1 Aug

YYZ12:09 p.m.Toronto Pearson Intl

6h 58m

1 stop

MDW6:07 p.m.Chicago Midway

C$ 401

KLM

21 Jul

MDW9:19 a.m.Chicago Midway

7h 05m

1 stop

YYZ5:24 p.m.Toronto Pearson Intl

28 Jul

YYZ12:09 p.m.Toronto Pearson Intl

7h 16m

1 stop

MDW6:25 p.m.Chicago Midway

C$ 514

Delta flights from Chicago Midway Airport to Canada

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

Delta

14 Sep

MDW9:30 a.m.Chicago Midway

3h 04m

1 stop

YYZ1:34 p.m.Toronto Pearson Intl

18 Sep

YYZ6:00 a.m.Toronto Pearson Intl

7h 34m

1 stop

MDW12:34 p.m.Chicago Midway

C$ 380

Delta

29 Aug

MDW1:27 p.m.Chicago Midway

8h 32m

1 stop

YYZ10:59 p.m.Toronto Pearson Intl

5 Sep

YYZ9:45 a.m.Toronto Pearson Intl

8h 14m

1 stop

MDW4:59 p.m.Chicago Midway

C$ 392

Delta

2 Jul

MDW1:26 p.m.Chicago Midway

8h 36m

1 stop

YYZ11:02 p.m.Toronto Pearson Intl

4 Jul

YYZ6:05 a.m.Toronto Pearson Intl

7h 41m

1 stop

MDW12:46 p.m.Chicago Midway

C$ 404

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

Quickest round-trip

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 14/7

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

Toronto Island

Wed 15/7

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 302

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 25/6

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Mon 29/6

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 304

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 27/6

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

Toronto Island

Mon 29/6

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 305

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 17/7

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Tue 21/7

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 308

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 29/6

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

Toronto Island

Tue 21/7

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 309

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 12/9

9:30 a.m.-3:18 p.m.

1 stop4h 48m

Toronto Pearson Intl

Sat 19/9

9:45 a.m.-12:34 p.m.

1 stop3h 49m

C$ 380

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 1/9

9:24 a.m.-5:24 p.m.

1 stop7h 00m

Toronto Pearson Intl

Sun 6/9

6:10 a.m.-9:17 a.m.

1 stop4h 07m

C$ 392

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Sat 25/7

9:19 a.m.-3:20 p.m.

1 stop5h 01m

Toronto Pearson Intl

Sat 1/8

12:09 p.m.-6:07 p.m.

1 stop6h 58m

C$ 401

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 25/6

10:25 a.m.-8:40 a.m.

1 stop22h 15m

Winnipeg

Mon 29/6

8:10 p.m.-9:40 a.m.

1 stop13h 30m

C$ 564

ChicagoHalifax

MDW - YHZ

MDWYHZ

Chicago Midway

Fri 3/7

10:25 a.m.-11:22 p.m.

1 stop10h 57m

Halifax Intl

Sat 11/7

11:00 p.m.-9:40 a.m.

1 stop12h 40m

C$ 577

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

Other information

What is the cheapest month to fly to Canada?

In general, March 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$ 81. If you’re not able to fly to Canada in March, then July is your next best option. Flight prices from Chicago Midway Airport to Canada during July average around C$ 86.

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

Our data shows that Friday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as C$ 319. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 733. 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$ 364. 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$ 397 per ticket.

Can stopping save me money on Chicago Midway Airport to Canada flights?

You could potentially save up to 20% 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$ 148
Fastest flight time	1h 40m
Direct flights	Every day
Airports in Canada	515 airports

The best one-way flight to Canada from Chicago Midway Airport in the past 72 hours is C$ 148. The best round-trip flight deal from Chicago Midway Airport to Canada found on momondo in the last 72 hours is C$ 320.

The fastest flight from Chicago Midway Airport to Canada takes 1h 40m

Direct flights go from Chicago Midway Airport to Canada every day.

There are 515 airports in Canada. From Chicago Midway Airport there are direct flights to Toronto Island (YTZ).

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 40.90% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 11.93%, Embraer 175 with 10.03%, and Embraer 170 with 7.61%.

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.

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Popular Cities in Canada

Flights to Torontofrom C$ 139

Flights to Vancouverfrom C$ 109

Flights to Montrealfrom C$ 295

Flights to Calgaryfrom C$ 149

Flights to Winnipegfrom C$ 151

Flights to Ottawafrom C$ 269

Flights to Halifaxfrom C$ 169

Flights to Kelownafrom C$ 130

Flights to Saskatoonfrom C$ 226

Flights to Reginafrom C$ 245

Flights to St. John'sfrom C$ 276

Flights to Québec Cityfrom C$ 321

Cheap flights from Chicago Midway Airport to Canada from C$ 135

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Canada departing on 26/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Chicago Midway Airport to Canada

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KLM flights from Chicago Midway Airport to Canada

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

Delta flights from Chicago Midway Airport to Canada

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

momondo Fare Finder

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

See travel insights to Canada from

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

What is the cheapest month to fly to Canada?

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

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

Can stopping save me money on Chicago Midway Airport to Canada flights?

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

How often are flights from Chicago to Canada delayed?

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

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

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

How many flights depart from Chicago Midway Airport to Canada on average per week?

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

Fastest flight time

Direct flights

Airports in Canada

Frequently asked questions about flying from Chicago Midway Airport to Canada

Why use momondo?

An easier way to manage your Canada trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Canada

Popular Cities in Canada

Popular flights according to clicks in the last 7 days on momondo

Chicago Midway Airport flight routes

According to popular flight searches on momondo this year

Canada flight routes

According to popular flight searches on momondo this year

Fly your favourite airline to Canada

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

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List of cabin classes available on flights landing in Canada. Availability may vary depending on flight origin and airline.

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