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Cheap flights from Canada to Chicago from $106

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 departing on 9/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Canada to Chicago

Recent round-trip flight deals from Canada to Chicago

Porter Airlines Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$173Porter Airlines
Find Deal
Thu, Aug 28 - Tue, Sep 2
Porter Airlines Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
10:40 am - 1:20 pmMDW-YTZ
1h 40mnonstop
$174Porter Airlines
Find Deal
Thu, Aug 28 - Sun, Aug 31
Air Transat Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
Air Transat Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
$211Air Transat
Find Deal
Fri, Oct 31 - Mon, Nov 3
Delta Logo
6:30 am - 8:35 amYYZ-MDW
3h 05m1 stop
Delta Logo
9:31 am - 1:32 pmMDW-YYZ
3h 01m1 stop
$212Delta
Find Deal
Thu, Sep 4 - Sun, Sep 7
Delta Logo
6:00 am - 1:03 pmYYZ-MDW
8h 03m1 stop
Delta Logo
6:15 pm - 10:56 pmMDW-YYZ
3h 41m1 stop
$213Delta
Find Deal
Thu, Sep 11 - Sat, Sep 13
Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$222
Find Deal
Thu, Sep 11 - Sun, Sep 14
Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$224
Find Deal
Fri, Sep 5 - Mon, Sep 8
Air Transat Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
Air Transat Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
$227Air Transat
Find Deal
Thu, Aug 21 - Mon, Aug 25
WestJet Logo
1:20 pm - 9:26 pmYYZ-MDW
9h 06m1 stop
WestJet Logo
10:31 am - 4:57 pmMDW-YYZ
5h 26m1 stop
$261WestJet
Find Deal
Wed, Sep 3 - Sat, Sep 6
WestJet Logo
6:00 am - 5:35 pmYYZ-MDW
12h 35m1 stop
WestJet Logo
1:43 pm - 11:20 pmMDW-YYZ
8h 37m1 stop
$262WestJet
Find Deal
Tue, Sep 30 - Sat, Oct 4

Porter Airlines flights from Canada to Chicago Midway Airport

Our best Porter Airlines deals on Canada to Chicago Midway Airport flight tickets
Porter Airlines
Aug 28
YTZ7:55 amToronto Island
1h 50m
MDW8:45 amChicago Midway
Sep 2
MDW9:35 amChicago Midway
1h 42m
YTZ12:17 pmToronto Island
$173
Find similar
Porter Airlines
Aug 28
YTZ7:55 amToronto Island
1h 50m
MDW8:45 amChicago Midway
Aug 31
MDW10:40 amChicago Midway
1h 40m
YTZ1:20 pmToronto Island
$174
Find similar
Porter Airlines
Sep 1
YTZ9:00 amToronto Island
1h 50m
MDW9:50 amChicago Midway
Sep 4
MDW5:20 pmChicago Midway
1h 42m
YTZ8:02 pmToronto Island
$175
Find similar

Air Transat flights from Canada to Chicago Midway Airport

Our best Air Transat deals on Canada to Chicago Midway Airport flight tickets
Air Transat
Oct 31
YTZ2:30 pmToronto Island
1h 50m
MDW3:20 pmChicago Midway
Nov 3
MDW11:00 amChicago Midway
1h 42m
YTZ1:42 pmToronto Island
$211
Find similar
Air Transat
Aug 21
YTZ7:55 amToronto Island
1h 50m
MDW8:45 amChicago Midway
Aug 25
MDW9:40 amChicago Midway
1h 40m
YTZ12:20 pmToronto Island
$227
Find similar
Air Transat
Oct 7
YTZ7:50 amToronto Island
1h 49m
MDW8:39 amChicago Midway
Oct 7
MDW5:20 pmChicago Midway
1h 42m
YTZ8:02 pmToronto Island
$264
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Canada to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 3, 2025.
Use the filters below to find and compare flights from Canada to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 8/28

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Tue 9/2

9:35 am-12:17 pm

Nonstop1h 42m

$173

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 8/28

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Sun 8/31

10:40 am-1:20 pm

Nonstop1h 40m

$174

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 10/31

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Mon 11/3

11:00 am-1:42 pm

Nonstop1h 42m

$211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 9/4

6:30 am-8:35 am

1 stop3h 05m

Chicago Midway

Sun 9/7

9:31 am-1:32 pm

1 stop3h 01m

$212

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 9/11

6:00 am-1:03 pm

1 stop8h 03m

Chicago Midway

Sat 9/13

6:15 pm-10:56 pm

1 stop3h 41m

$213

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 9/11

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

Sun 9/14

5:20 pm-8:02 pm

Nonstop1h 42m

$222

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 9/5

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Mon 9/8

5:20 pm-8:02 pm

Nonstop1h 42m

$224

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 8/21

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Mon 8/25

9:40 am-12:20 pm

Nonstop1h 40m

$227

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 9/3

1:20 pm-9:26 pm

1 stop9h 06m

Chicago Midway

Sat 9/6

10:31 am-4:57 pm

1 stop5h 26m

$261

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 9/30

6:00 am-5:35 pm

1 stop12h 35m

Chicago Midway

Sat 10/4

1:43 pm-11:20 pm

1 stop8h 37m

$262

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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 month to fly to Chicago Midway Airport?

The month of May is, on average, the cheapest month to fly to Chicago Midway Airport from Canada, with most prices found around $206. If you are unable to visit Chicago Midway Airport during the month of May, then departing from Canada during the month February is also very affordable. Most momondo users find prices during this month for around $213.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Canada. The lowest ticket price found for a Wednesday departure recently was $242. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Thursday is the most expensive day to depart from Canada because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $279.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Canada in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $240 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $284. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Canada to Chicago Midway flight route?

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

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

There are 4 cabin classes available to choose from on Canada to Chicago Midway 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 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

$106

Fastest flight time

1h 49m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Canada in the past 72 hours is $106. The best round-trip flight deal from Canada to Chicago Midway Airport found on momondo in the last 72 hours is $173.
The fastest flight from Canada to Chicago Midway Airport takes 1h 49m
Direct flights go from Canada to Chicago Midway Airport every day.
Search flight deals

  • 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 $158Free CancellationRating
8.0
319 reviews
Search Porter Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

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.

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