Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Canada to Chicago Midway Airport from $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 Canada to Chicago Midway Airport departing on 12/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags
"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Canada to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Canada to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Canada to Chicago.

Cheap last minute flights

Planning a quick getaway from Canada to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals to Chicago

Find recent round-trip train or bus tickets from Canada to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
6:35 am - 5:47 pmYYC-MDW
10h 12m1 stop
9:34 am - 8:53 pmMDW-YYC
12h 19m2 stops
$221Delta
Find Deal
Thu, Jan 9 - Sun, Jan 12
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$225Porter Airlines
Find Deal
Thu, Nov 28 - Mon, Dec 2
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$226Porter Airlines
Find Deal
Thu, Nov 28 - Mon, Dec 2
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$228Porter Airlines
Find Deal
Fri, Feb 7 - Mon, Feb 10
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$230Porter Airlines
Find Deal
Thu, Dec 19 - Sun, Jan 5
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$249Air Transat
Find Deal
Thu, Nov 28 - Mon, Dec 2
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$252Air Transat
Find Deal
Thu, Nov 28 - Mon, Dec 2
6:35 am - 5:47 pmYYC-MDW
10h 12m1 stop
9:34 am - 8:53 pmMDW-YYC
12h 19m2 stops
$252Delta
Find Deal
Mon, Jan 27 - Thu, Jan 30
6:30 am - 1:35 pmYYZ-MDW
8h 05m1 stop
2:15 pm - 11:34 pmMDW-YYZ
8h 19m1 stop
$303WestJet
Find Deal
Tue, Dec 3 - Tue, Dec 10
6:30 am - 6:32 pmYYZ-MDW
13h 02m1 stop
12:44 pm - 7:06 pmMDW-YYZ
5h 22m1 stop
$304WestJet
Find Deal
Sat, Dec 7 - Tue, Dec 10
11:00 pm - 11:29 pmYVR-MDW
22h 29m1 stop
Fri, Dec 6
8:00 am - 10:06 pmYYC-MDW
13h 06m2 stops
$136Delta
Find Deal
Sat, Dec 7
8:35 pm - 3:11 pmYVR-MDW
16h 36m2 stops
Mon, Dec 16
7:00 am - 6:32 pmYYC-MDW
10h 32m1 stop
$137Delta
Find Deal
Thu, Dec 12
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
$140Porter Airlines
Find Deal
Thu, Dec 5
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$141Porter Airlines
Find Deal
Wed, Jan 1
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
$152Air Transat
Find Deal
Tue, Feb 11
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
$154Air Transat
Find Deal
Tue, Dec 10
6:30 am - 6:32 pmYYZ-MDW
13h 02m1 stop
$175WestJet
Find Deal
Sat, Dec 7
6:30 am - 6:32 pmYYZ-MDW
13h 02m1 stop
$187WestJet
Find Deal
Mon, Dec 9
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$353Porter Airlines
Find Deal
Wed, Nov 6 - Sun, Nov 17
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$386Porter Airlines
Find Deal
Sat, Nov 9 - Tue, Nov 12
11:39 am - 9:38 pmYYZ-MDW
10h 59m1 stop
9:30 am - 11:34 pmMDW-YYZ
13h 04m1 stop
$405WestJet
Find Deal
Sat, Nov 9 - Tue, Nov 12
1:25 pm - 9:38 pmYYZ-MDW
9h 13m1 stop
12:43 pm - 11:59 pmMDW-YYZ
10h 16m1 stop
$441WestJet
Find Deal
Sat, Nov 9 - Mon, Nov 11
6:50 am - 12:00 pmYUL-MDW
6h 10m1 stop
2:17 pm - 11:33 pmMDW-YUL
8h 16m1 stop
Sat, Nov 9 - Wed, Nov 20
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$467Air Transat
Find Deal
Fri, Nov 8 - Sun, Nov 10
11:50 am - 4:40 pmYUL-MDW
5h 50m1 stop
10:32 pm - 4:35 pmMDW-YUL
17h 03m1 stop
Thu, Nov 7 - Mon, Nov 11
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
12:55 pm - 3:37 pmMDW-YTZ
1h 42mnonstop
$494Air Transat
Find Deal
Wed, Nov 6 - Sat, Nov 9
6:00 am - 8:55 amYYZ-MDW
3h 55m1 stop
1:30 pm - 10:36 pmMDW-YYZ
8h 06m1 stop
$617Delta
Find Deal
Sat, Nov 9 - Mon, Nov 11
9:45 am - 5:03 pmYYZ-MDW
8h 18m1 stop
9:35 am - 6:28 pmMDW-YYZ
7h 53m1 stop
$706Delta
Find Deal
Fri, Nov 8 - Sun, Nov 10
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$225Porter Airlines
Find Deal
Thu, Nov 28 - Mon, Dec 2
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$226Porter Airlines
Find Deal
Thu, Nov 28 - Mon, Dec 2
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$228Porter Airlines
Find Deal
Fri, Feb 7 - Mon, Feb 10
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$230Porter Airlines
Find Deal
Thu, Dec 19 - Sun, Jan 5
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$233Porter Airlines
Find Deal
Sun, Nov 24 - Wed, Dec 25
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$234Porter Airlines
Find Deal
Fri, Dec 13 - Thu, Dec 19
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$249Air Transat
Find Deal
Thu, Nov 28 - Mon, Dec 2
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$252Air Transat
Find Deal
Thu, Nov 28 - Mon, Dec 2
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
12:55 pm - 3:37 pmMDW-YTZ
1h 42mnonstop
$260Air Transat
Find Deal
Thu, Jan 30 - Tue, Feb 4
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
Fri, Nov 15 - Mon, Nov 18

Air Transat flights from Canada to Chicago Midway Airport

Our best Air Transat deals on Canada to Chicago Midway Airport flight tickets
Air Transat
Nov 28
YTZ9:30 amToronto Island
1h 50m
MDW10:20 amChicago Midway
Dec 2
MDW5:35 pmChicago Midway
1h 42m
YTZ8:17 pmToronto Island
Air Transat
Nov 28
YTZ9:30 amToronto Island
1h 50m
MDW10:20 amChicago Midway
Dec 2
MDW12:05 pmChicago Midway
1h 42m
YTZ2:47 pmToronto Island
Air Transat
Jan 30
YTZ11:10 amToronto Island
1h 50m
MDW12:00 pmChicago Midway
Feb 4
MDW12:55 pmChicago Midway
1h 42m
YTZ3:37 pmToronto Island

Porter Airlines flights from Canada to Chicago Midway Airport

Our best Porter Airlines deals on Canada to Chicago Midway Airport flight tickets
Porter Airlines
Nov 28
YTZ3:50 pmToronto Island
1h 50m
MDW4:40 pmChicago Midway
Dec 2
MDW12:05 pmChicago Midway
1h 42m
YTZ2:47 pmToronto Island
Porter Airlines
Nov 28
YTZ9:30 amToronto Island
1h 50m
MDW10:20 amChicago Midway
Dec 2
MDW5:35 pmChicago Midway
1h 42m
YTZ8:17 pmToronto Island
Porter Airlines
Feb 7
YTZ11:20 amToronto Island
1h 50m
MDW12:10 pmChicago Midway
Feb 10
MDW1:05 pmChicago Midway
1h 42m
YTZ3:47 pmToronto Island

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

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

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

Porter Airlines. Porter Airlines is the most popular carrier operating from Canada to Chicago Midway Airport

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

No. A direct flight is the cheapest option for a flight between Canada to Chicago Midway Airport.

Cheap Canada to Chicago Midway Airport flight deals and tips

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

Best Price Found

$135

Fastest flight time

1h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Canada in the past 72 hours is $135. The best round-trip flight deal from Canada to Chicago Midway Airport found on momondo in the last 72 hours is $221.
The fastest flight from Canada to Chicago Midway Airport takes 1h 50m
Direct flights go from Canada to Chicago Midway Airport every day.

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

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

  • How many operators does momondo search for flights from Canada to Chicago Midway Airport?

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

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Canada to Chicago Midway Airport?


Best airlines flying from Canada to Chicago Midway Airport

Compare and see reviews for airlines that fly from Canada to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom $205Free CancellationRating
7.8
293 reviews
Search Porter Airlines flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Canada.

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

Yes. momondo enables you to select and highlight flights to Chicago from Canada with this policy.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Canada.

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

Yes. momondo can track prices for Canada to Chicago 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.


An easier way to manage your Chicago Midway Airport 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.
1 adult
From?
To?
Sat 11/9
Sat 11/16
Email me momondo's favorite deals

Find better results for your trip to Chicago