Cheap flights from Canada to Chicago from $195

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Canada to Chicago

Recent round-trip flight deals from Canada to Chicago

Enter your travel dates to find the best prices.
Delta Logo
8:45 am - 4:53 pmYYC  Calgary-MDW Chicago Midway
8h 08m1 stop Minneapolis St Paul
Delta Logo
12:44 pm - 10:01 pmMDW  Chicago Midway-YYC Calgary
9h 17m1 stop Minneapolis St Paul
$325Delta
Thu, Jan 21 - Mon, Jan 25
Delta Logo
8:45 am - 4:53 pmYYC  Calgary-MDW Chicago Midway
8h 08m1 stop Minneapolis St Paul
Delta Logo
9:38 am - 10:01 pmMDW  Chicago Midway-YYC Calgary
12h 23m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$325Delta
Thu, Jan 21 - Wed, Jan 27
Delta Logo
8:45 am - 6:00 pmYYC  Calgary-MDW Chicago Midway
9h 15m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
Delta Logo
9:38 am - 10:01 pmMDW  Chicago Midway-YYC Calgary
12h 23m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$325Delta
Fri, Jan 22 - Wed, Jan 27
Delta Logo
8:45 am - 4:53 pmYYC  Calgary-MDW Chicago Midway
8h 08m1 stop Minneapolis St Paul
Delta Logo
9:38 am - 10:01 pmMDW  Chicago Midway-YYC Calgary
12h 23m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$325Delta
Fri, Jan 22 - Thu, Jan 28
Delta Logo
8:45 am - 4:53 pmYYC  Calgary-MDW Chicago Midway
8h 08m1 stop Minneapolis St Paul
Delta Logo
12:44 pm - 10:01 pmMDW  Chicago Midway-YYC Calgary
9h 17m1 stop Minneapolis St Paul
$325Delta
Fri, Jan 22 - Tue, Jan 26
Delta Logo
8:45 am - 6:00 pmYYC  Calgary-MDW Chicago Midway
9h 15m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
Delta Logo
9:38 am - 10:01 pmMDW  Chicago Midway-YYC Calgary
12h 23m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$325Delta
Thu, Jan 21 - Thu, Jan 28
Delta Logo
8:45 am - 4:53 pmYYC  Calgary-MDW Chicago Midway
8h 08m1 stop Minneapolis St Paul
Delta Logo
12:44 pm - 10:01 pmMDW  Chicago Midway-YYC Calgary
9h 17m1 stop Minneapolis St Paul
$325Delta
Thu, Jan 21 - Tue, Jan 26
Delta Logo
8:45 am - 4:53 pmYYC  Calgary-MDW Chicago Midway
8h 08m1 stop Minneapolis St Paul
Delta Logo
9:38 am - 10:01 pmMDW  Chicago Midway-YYC Calgary
12h 23m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$325Delta
Fri, Jan 22 - Wed, Jan 27
Delta Logo
8:45 am - 6:00 pmYYC  Calgary-MDW Chicago Midway
9h 15m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
Delta Logo
9:38 am - 10:01 pmMDW  Chicago Midway-YYC Calgary
12h 23m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$325Delta
Fri, Jan 22 - Sun, Jan 24
Delta Logo
8:45 am - 6:00 pmYYC  Calgary-MDW Chicago Midway
9h 15m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
Delta Logo
9:38 am - 10:01 pmMDW  Chicago Midway-YYC Calgary
12h 23m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$325Delta
Fri, Jan 22 - Thu, Jan 28

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Delta flights from Canada to Chicago Midway Airport

Our best Delta deals on Canada to Chicago Midway Airport flight tickets
Delta
Jan 22
YYC8:45 amCalgary
9h 15m
2 stops
MDW6:00 pmChicago Midway
Jan 24
MDW9:38 amChicago Midway
12h 23m
2 stops
YYC10:01 pmCalgary
$325
Delta
Dec 3
YYZ6:00 amToronto Pearson Intl
4h 37m
1 stop
MDW9:37 amChicago Midway
Dec 6
MDW1:41 pmChicago Midway
8h 26m
1 stop
YYZ11:07 pmToronto Pearson Intl
$331
Delta
Dec 3
YYZ6:00 amToronto Pearson Intl
4h 37m
1 stop
MDW9:37 amChicago Midway
Dec 6
MDW1:41 pmChicago Midway
8h 26m
1 stop
YYZ11:07 pmToronto Pearson Intl
$332

WestJet flights from Canada to Chicago Midway Airport

Our best WestJet deals on Canada to Chicago Midway Airport flight tickets
WestJet
Jan 23
YYC8:49 amCalgary
8h 08m
1 stop
MDW4:57 pmChicago Midway
Jan 26
MDW12:48 pmChicago Midway
9h 17m
1 stop
YYC10:05 pmCalgary
$358
WestJet
Jan 27
YYZ6:14 amToronto Pearson Intl
7h 51m
1 stop
MDW1:05 pmChicago Midway
Jan 30
MDW1:45 pmChicago Midway
8h 18m
1 stop
YYZ11:03 pmToronto Pearson Intl
$365
WestJet
Nov 26
YYZ6:04 amToronto Pearson Intl
6h 25m
1 stop
MDW11:29 amChicago Midway
Nov 29
MDW1:35 pmChicago Midway
8h 26m
1 stop
YYZ11:01 pmToronto Pearson Intl
$379

momondo Fare Finder

 
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

Cheapest round-trip
Quickest round-trip

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 1/21

8:45 am-4:53 pm

1 stop8h 08m

Chicago Midway

Mon 1/25

12:44 pm-10:01 pm

1 stop9h 17m

$325

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 1/21

8:45 am-4:53 pm

1 stop8h 08m

Chicago Midway

Wed 1/27

9:38 am-10:01 pm

2 stops12h 23m

$325

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 1/22

8:45 am-6:00 pm

2 stops9h 15m

Chicago Midway

Wed 1/27

9:38 am-10:01 pm

2 stops12h 23m

$325

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 1/22

8:45 am-4:53 pm

1 stop8h 08m

Chicago Midway

Thu 1/28

9:38 am-10:01 pm

2 stops12h 23m

$325

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 1/22

8:45 am-4:53 pm

1 stop8h 08m

Chicago Midway

Tue 1/26

12:44 pm-10:01 pm

1 stop9h 17m

$325

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 1/21

8:45 am-6:00 pm

2 stops9h 15m

Chicago Midway

Thu 1/28

9:38 am-10:01 pm

2 stops12h 23m

$325

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 1/21

8:45 am-4:53 pm

1 stop8h 08m

Chicago Midway

Tue 1/26

12:44 pm-10:01 pm

1 stop9h 17m

$325

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 1/22

8:45 am-4:53 pm

1 stop8h 08m

Chicago Midway

Wed 1/27

9:38 am-10:01 pm

2 stops12h 23m

$325

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 1/22

8:45 am-6:00 pm

2 stops9h 15m

Chicago Midway

Sun 1/24

9:38 am-10:01 pm

2 stops12h 23m

$325

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 1/22

8:45 am-6:00 pm

2 stops9h 15m

Chicago Midway

Thu 1/28

9:38 am-10:01 pm

2 stops12h 23m

$325

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 January is, on average, the cheapest month to fly to Chicago Midway Airport from Canada, with most prices found around $204. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Canada during the month December is also very affordable. Most momondo users find prices during this month for around $221.

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

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Canada. The lowest ticket price found for a Tuesday departure recently was $229. 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, Friday 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 $349.

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

Flying to Chicago Midway Airport from Canada at noon is the least expensive time of day to depart. momondo users have found prices as low as $274 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $290. 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 Airport flights?

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

You could potentially save up to 28% on your flight if you consider stops on a Canada to Chicago Midway Airport flight.

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

$195

Fastest flight time

3h 38m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Canada in the past 72 hours is $195. The best round-trip flight deal from Canada to Chicago Midway Airport found on momondo in the last 72 hours is $325.
The fastest flight from Canada to Chicago Midway Airport takes 3h 38m
There are no direct flights from Canada to Chicago Midway Airport. There are no popular flight routes from Canada to Chicago Midway Airport.

Frequently asked questions about flying from Canada to Chicago Midway Airport

  • 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 $185Free CancellationRating
8.0
468 reviews
Search Porter Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Munster
Chesterton
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Crown Point
Porter
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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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1 adult
Wed 12/9
Wed 12/16

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