Cheap flights from Illinois to Canada from $97

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Canada departing on 9/22. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
10:30 am - 1:10 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
$221Porter Airlines
Thu, May 28 - Sun, May 31
Porter Airlines Logo
10:30 am - 1:10 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
$223Porter Airlines
Thu, May 28 - Sun, May 31
Air Canada Logo
7:25 am - 10:06 am
ORD
-
YTZ
1h 41mnonstop
Air Canada Logo
12:15 pm - 1:10 pm
YTZ
-
ORD
1h 55mnonstop
$226Air Canada
Tue, Jun 2 - Tue, Jun 9
Air Canada Logo
7:25 am - 10:06 am
ORD
-
YTZ
1h 41mnonstop
Air Canada Logo
12:15 pm - 1:10 pm
YTZ
-
ORD
1h 55mnonstop
$227Air Canada
Wed, Jun 3 - Wed, Jun 10
WestJet Logo
6:00 am - 9:48 pm
ORD
-
YYC
16h 48m
1 stop
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
$264WestJet
Sat, May 23 - Fri, May 29
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
$265WestJet
Sun, Aug 16 - Fri, Aug 21
United Airlines Logo
7:44 pm - 10:37 pm
ORD
-
YYC
3h 53mnonstop
United Airlines Logo
8:30 am - 1:07 pm
YYC
-
ORD
3h 37mnonstop
$268United Airlines
Tue, May 26 - Sat, May 30
United Airlines Logo
6:00 am - 9:48 pm
ORD
-
YYC
16h 48m
1 stop
United Airlines Logo
12:28 pm - 5:05 pm
YYC
-
ORD
3h 37mnonstop
$277United Airlines
Tue, May 26 - Thu, May 28
Delta Logo
9:22 am - 1:30 pm
MDW
-
YYZ
3h 08m
1 stop
Delta Logo
6:30 am - 1:19 pm
YYZ
-
MDW
7h 49m
1 stop
$304Delta
Thu, May 28 - Sun, May 31
Delta Logo
1:59 pm - 8:30 pm
MDW
-
YYC
7h 31m
1 stop
Delta Logo
6:45 am - 5:56 pm
YYC
-
MDW
10h 11m
1 stop
$323Delta
Wed, May 27 - Sun, May 31

Air Canada flights from Illinois to Canada

Our best Air Canada deals on Illinois to Canada flight tickets
Air Canada
Jun 2
ORD7:25 amChicago O'Hare Intl
1h 41m
YTZ10:06 amToronto Island
Jun 9
YTZ12:15 pmToronto Island
1h 55m
ORD1:10 pmChicago O'Hare Intl
$226
Air Canada
Jun 3
ORD7:25 amChicago O'Hare Intl
1h 41m
YTZ10:06 amToronto Island
Jun 10
YTZ12:15 pmToronto Island
1h 55m
ORD1:10 pmChicago O'Hare Intl
$227
Air Canada
May 28
ORD9:55 amChicago O'Hare Intl
1h 40m
YYZ12:35 pmToronto Pearson Intl
May 31
YYZ6:40 pmToronto Pearson Intl
2h 00m
ORD7:40 pmChicago O'Hare Intl
$229

American Airlines flights from Illinois to Canada

Our best American Airlines deals on Illinois to Canada flight tickets
American Airlines
Jun 6
ORD5:00 amChicago O'Hare Intl
8h 59m
1 stop
YYZ2:59 pmToronto Pearson Intl
Jun 13
YYZ7:25 amToronto Pearson Intl
2h 10m
ORD8:35 amChicago O'Hare Intl
$288
American Airlines
May 29
ORD8:30 pmChicago O'Hare Intl
1h 54m
YYZ11:24 pmToronto Pearson Intl
Jun 1
YYZ6:02 pmToronto Pearson Intl
7h 36m
1 stop
ORD12:38 amChicago O'Hare Intl
$294
American Airlines
May 26
ORD8:55 pmChicago O'Hare Intl
3h 48m
YYC11:43 pmCalgary
May 30
YYC6:45 amCalgary
12h 36m
1 stop
ORD8:21 pmChicago O'Hare Intl
$297

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Canada 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 May 9, 2026.
Use the filters below to find and compare flights from Illinois 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

Thu 5/28

10:30 am-1:10 pm

Nonstop1h 40m

Toronto Island

Sun 5/31

1:45 pm-2:35 pm

Nonstop1h 50m

$221

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 5/28

10:30 am-1:10 pm

Nonstop1h 40m

Toronto Island

Sun 5/31

8:55 am-9:45 am

Nonstop1h 50m

$223

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Tue 6/2

7:25 am-10:06 am

Nonstop1h 41m

Toronto Island

Tue 6/9

12:15 pm-1:10 pm

Nonstop1h 55m

$226

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Wed 6/3

7:25 am-10:06 am

Nonstop1h 41m

Toronto Island

Wed 6/10

12:15 pm-1:10 pm

Nonstop1h 55m

$227

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 5/23

6:00 am-9:48 pm

1 stop16h 48m

Calgary

Fri 5/29

12:00 pm-4:40 pm

Nonstop3h 40m

$264

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 8/16

5:30 pm-8:25 pm

Nonstop3h 55m

Calgary

Fri 8/21

12:00 pm-4:40 pm

Nonstop3h 40m

$265

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 5/26

7:44 pm-10:37 pm

Nonstop3h 53m

Calgary

Sat 5/30

8:30 am-1:07 pm

Nonstop3h 37m

$268

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 5/26

6:00 am-9:48 pm

1 stop16h 48m

Calgary

Thu 5/28

12:28 pm-5:05 pm

Nonstop3h 37m

$277

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Thu 5/28

9:22 am-1:30 pm

1 stop3h 08m

Toronto Pearson Intl

Sun 5/31

6:30 am-1:19 pm

1 stop7h 49m

$304

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 5/27

1:59 pm-8:30 pm

1 stop7h 31m

Calgary

Sun 5/31

6:45 am-5:56 pm

1 stop10h 11m

$323

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 Canada from

How to get the cheapest flight ticket from Illinois 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

What is the cheapest month to fly to Canada?

If you aren’t able to travel during the month of October, then book flights to Canada from Illinois during November instead. Flights to Canada in November, while not as cheap as those in October, still average around $276.

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 $423. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Illinois to Canada for around $717.

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

In the evening is the cheapest time of day to fly from Illinois to Canada when you can find flight prices for as low as $410. Flying to Canada in the evening is an ideal time because this is during off-peak travel hours. In contrast, the most expensive time of day to depart to Canada is in the afternoon when prices are around $742.

What is the cheapest Illinois to Canada flight route?

Fly from Chicago O'Hare Intl to Calgary for the best Illinois - Canada flight prices

How far in advance should I book a flight from Illinois to Canada?

You are more likely to see cheaper flights to Canada from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Canada for around $305 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Canada from Illinois for as low as $203 on momondo.

Can stopping save me money on Illinois to Canada flights?

No. A direct flight is the cheapest option for a flight between Illinois to Canada.

Cheap Illinois to Canada flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Canada

Best Price Found

$106

Fastest flight time

1h 35m

Direct flights

Every day

Airports in Canada

515 airports
The best one-way flight to Canada from Illinois in the past 72 hours is $106. The best round-trip flight deal from Illinois to Canada found on momondo in the last 72 hours is $217.
The fastest flight from Illinois to Canada takes 1h 35m
Direct flights go from Illinois to Canada every day.
There are 515 airports in Canada. From Illinois there are direct flights to Toronto Pearson Intl (YYZ), Toronto Island (YTZ).

Frequently asked questions about flying from Illinois to Canada

  • When did momondo last update prices for flights from Illinois to Canada?

    Prices for flights from Illinois to Canada are refreshed on a daily basis.

  • How many operators does momondo search for flights from Illinois to Canada?

  • How old do you have to be to fly from Illinois to Canada?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Illinois to Canada.

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

    The travel and health documents you'll need for your trip to Canada 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 Canada. 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 Illinois to Canada?

Best airlines flying from Illinois to Canada

Compare and see reviews for airlines that fly from Illinois to Canada with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $74Free CancellationRating
7.1
11,012 reviews
Search Air Canada flights
DeltaPriceFrom $88Free CancellationRating
7.9
8,457 reviews
Search Delta flights
United AirlinesPriceFrom $90Free CancellationRating
7.4
9,696 reviews
Search United Airlines flights
WestJetPriceFrom $121Free CancellationRating
7.2
3,332 reviews
Search WestJet flights
Qantas AirwaysPriceFrom $160Free CancellationRating
7.5
1,033 reviews
Search Qantas Airways flights
Porter AirlinesPriceFrom $160Free CancellationRating
8.0
437 reviews
Search Porter Airlines flights
American AirlinesPriceFrom $209Free CancellationRating
7.1
11,668 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $328Free CancellationRating
7.9
12,348 reviews
Search Alaska Airlines flights
Qatar AirwaysPriceFrom $381Free CancellationRating
7.4
3,729 reviews
Search Qatar Airways flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Illinois to Canada. Millions of users trust and use momondo every year so you are in good hands.

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

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

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

Once all potential Illinois 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 Illinois to Canada right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Canada from Illinois. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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1 adult
Mon 6/8
Mon 6/15

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