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Cheap flights from Canada to Chicago from $86

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 3/13. 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

Cheap round-trip flights

Recommended round-trip deals departing in the coming months from the most popular airlines that fly to Chicago.

Cheap one-way flights

Only flying one-way? Below are some of the best one-way flight deals to Chicago found on KAYAK recently.

Cheap last minute flights

Leaving soon but still want a bargain? Check out these latest deals for last minute flights to Chicago.

Cheap direct flights

The latest deals for direct flights to Chicago so you can sit back and relax without the need for a layover.

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.
8:30 am - 6:38 pmYYC-ORD
9h 08m1 stop
3:35 pm - 11:02 pmORD-YYC
8h 27m1 stop
$168Air Canada
Find Deal
lun., ene. 20 - lun., ene. 27
7:20 pm - 9:33 amYYC-ORD
13h 13m1 stop
12:58 pm - 11:18 pmORD-YYC
11h 20m1 stop
lun., mar. 17 - mar., mar. 18
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$197WestJet
Find Deal
jue., may. 22 - dom., may. 25
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$210WestJet
Find Deal
mié., jun. 18 - dom., jun. 22
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$230Porter Airlines
Find Deal
vie., feb. 14 - lun., feb. 17
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$231Porter Airlines
Find Deal
jue., feb. 13 - dom., feb. 16
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
9:49 am - 12:30 pmORD-YYZ
1h 41mnonstop
$256American Airlines
Find Deal
jue., ene. 23 - dom., ene. 26
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
6:00 am - 11:45 amORD-YYZ
4h 45m1 stop
$265American Airlines
Find Deal
jue., ene. 23 - dom., ene. 26
6:30 am - 12:44 pmYVR-ORD
4h 14mnonstop
3:40 pm - 6:13 pmORD-YVR
4h 33mnonstop
$270United Airlines
Find Deal
lun., mar. 10 - lun., mar. 17
10:30 am - 4:38 pmYVR-ORD
4h 08mnonstop
10:35 am - 9:18 pmORD-YVR
12h 43m2 stops
$278United Airlines
Find Deal
mar., feb. 4 - mar., feb. 11
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$86WestJet
Find Deal
jue., mar. 13
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$89WestJet
Find Deal
lun., mar. 3
8:30 am - 6:34 pmYYC-ORD
9h 04m1 stop
$97Air Canada
Find Deal
sáb., feb. 22
12:50 am - 10:04 amYYC-ORD
8h 14m1 stop
$103Air Canada
Find Deal
lun., feb. 17
7:20 pm - 9:33 amYYC-ORD
13h 13m1 stop
$113United Airlines
Find Deal
lun., mar. 17
7:20 pm - 11:19 amYYC-ORD
14h 59m1 stop
$126United Airlines
Find Deal
vie., mar. 21
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$134Porter Airlines
Find Deal
jue., feb. 13
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$141Porter Airlines
Find Deal
mar., feb. 18
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
$152American Airlines
Find Deal
mié., ene. 22
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
$163American Airlines
Find Deal
mié., ene. 15
6:29 am - 11:09 pmYYC-ORD
15h 40m1 stop
7:09 am - 9:55 pmORD-YYC
15h 46m1 stop
$302American Airlines
Find Deal
jue., dic. 26 - mié., ene. 1
8:10 am - 4:51 pmYVR-ORD
6h 41m1 stop
8:02 pm - 10:52 pmORD-YVR
4h 50mnonstop
$337Air Canada
Find Deal
mar., dic. 24 - mar., dic. 24
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$356Porter Airlines
Find Deal
mié., dic. 25 - sáb., ene. 25
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$357Porter Airlines
Find Deal
jue., dic. 26 - mié., ene. 29
5:15 pm - 4:40 pmYYZ-ORD
24h 25m1 stop
6:45 am - 10:52 pmORD-YYZ
15h 07m1 stop
$415WestJet
Find Deal
jue., dic. 26 - mié., ene. 29
5:15 pm - 4:40 pmYYZ-ORD
24h 25m1 stop
6:15 am - 6:18 amORD-YYZ
23h 03m2 stops
$424WestJet
Find Deal
jue., dic. 26 - mié., ene. 29
1:00 pm - 4:10 pmYYZ-MDW
4h 10m1 stop
9:34 am - 5:31 pmMDW-YYZ
6h 57m1 stop
$424Delta
Find Deal
mié., dic. 25 - sáb., ene. 25
3:30 pm - 4:41 pmYYZ-ORD
2h 11mnonstop
12:45 pm - 10:15 pmORD-YYZ
8h 30m1 stop
$428United Airlines
Find Deal
lun., dic. 23 - lun., ene. 6
6:35 pm - 7:32 pmYYZ-ORD
1h 57mnonstop
9:05 pm - 9:58 amORD-YYZ
11h 53m1 stop
$429United Airlines
Find Deal
lun., dic. 23 - lun., ene. 6
8:45 am - 10:52 pmYVR-ORD
12h 07m2 stops
1:55 pm - 10:55 pmORD-YVR
11h 00m1 stop
$452Delta
Find Deal
jue., dic. 26 - dom., dic. 29
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$197WestJet
Find Deal
jue., may. 22 - dom., may. 25
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$210WestJet
Find Deal
mié., jun. 18 - dom., jun. 22
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$230Porter Airlines
Find Deal
vie., feb. 14 - lun., feb. 17
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$231Porter Airlines
Find Deal
jue., feb. 13 - dom., feb. 16
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
9:49 am - 12:30 pmORD-YYZ
1h 41mnonstop
$256American Airlines
Find Deal
jue., ene. 23 - dom., ene. 26
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
8:11 am - 10:51 amORD-YYZ
1h 40mnonstop
$257American Airlines
Find Deal
sáb., ene. 18 - dom., feb. 2
6:30 am - 12:44 pmYVR-ORD
4h 14mnonstop
3:40 pm - 6:13 pmORD-YVR
4h 33mnonstop
$270United Airlines
Find Deal
lun., mar. 10 - lun., mar. 17
10:30 am - 4:38 pmYVR-ORD
4h 08mnonstop
1:10 pm - 3:50 pmORD-YVR
4h 40mnonstop
$273Air Canada
Find Deal
jue., ene. 16 - mié., ene. 22
10:30 am - 4:38 pmYVR-ORD
4h 08mnonstop
1:10 pm - 3:50 pmORD-YVR
4h 40mnonstop
$278United Airlines
Find Deal
mar., feb. 4 - mar., feb. 11
9:00 am - 10:10 amYYZ-ORD
2h 10mnonstop
2:05 pm - 4:46 pmORD-YYZ
1h 41mnonstop
$288Air Canada
Find Deal
mié., ene. 8 - vie., ene. 31

Lufthansa flights from Canada to Chicago

Our best Lufthansa deals on Canada to Chicago flight tickets
Lufthansa
Jan 16
YVR10:30 amVancouver Intl
4h 08m
ORD4:38 pmChicago O'Hare Intl
Jan 22
ORD3:40 pmChicago O'Hare Intl
4h 33m
YVR6:13 pmVancouver Intl
Lufthansa
Jan 2
YYZ9:00 pmToronto Pearson Intl
15h 58m
1 stop
ORD11:58 amChicago O'Hare Intl
Jan 4
ORD8:30 pmChicago O'Hare Intl
1h 41m
YYZ11:11 pmToronto Pearson Intl

Delta flights from Canada to Chicago

Our best Delta deals on Canada to Chicago flight tickets
Delta
Jan 19
YYC6:35 amCalgary
9h 54m
1 stop
ORD5:29 pmChicago O'Hare Intl
Jan 26
ORD1:45 pmChicago O'Hare Intl
10h 33m
1 stop
YYC11:18 pmCalgary
Delta
Jan 19
YYC6:35 amCalgary
7h 55m
1 stop
ORD3:30 pmChicago O'Hare Intl
Jan 26
ORD1:45 pmChicago O'Hare Intl
10h 33m
1 stop
YYC11:18 pmCalgary
Delta
Jan 9
YYC6:35 amCalgary
9h 54m
1 stop
ORD5:29 pmChicago O'Hare Intl
Jan 12
ORD7:05 amChicago O'Hare Intl
17h 13m
2 stops
YYC11:18 pmCalgary

See travel insights to Chicago from

How to get the cheapest flight ticket from Canada to Chicago

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?

The month of April is, on average, the cheapest month to fly to Chicago from Canada, with most prices found around $239. If you’re not able to fly to Chicago in April, then February is your next best option. Flight prices from Canada to Chicago during February average around $243.

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

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $258. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Canada to Chicago for around $292.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Canada to Chicago during this time can be as low as $269. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $325.

What is the cheapest Canada to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from Canada is 48 days out, which is when prices tend to be around $296. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $241.

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

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

You could potentially save up to 12% on your flight if you consider stops on a Canada to Chicago flight.

Cheap Canada to Chicago flight deals and tips

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

Best Price Found

$86

Fastest flight time

1h 45m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Canada in the past 72 hours is $86. The best round-trip flight deal from Canada to Chicago found on momondo in the last 72 hours is $168.
The fastest flight from Canada to Chicago takes 1h 45m
Direct flights go from Canada to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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

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

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

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

    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 Canada to Chicago.

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

    The necessary travel and health documents for your Chicago 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 Canada to Chicago?


Best airlines flying from Canada to Chicago

Compare and see reviews for airlines that fly from Canada to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $112Free CancellationRating
7.4
9,035 reviews
Search United Airlines flights
Air CanadaPriceFrom $157Free CancellationRating
7.0
8,413 reviews
Search Air Canada flights
American AirlinesPriceFrom $166Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
WestJetPriceFrom $186Free CancellationRating
7.2
2,812 reviews
Search WestJet flights
Porter AirlinesPriceFrom $206Free CancellationRating
7.9
283 reviews
Search Porter Airlines flights
DeltaPriceFrom $268Free CancellationRating
8.0
8,597 reviews
Search Delta flights

Why use momondo?

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

Finding the right flight to Chicago from Canada is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. All flights to Chicago from Canada on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo helps you find the best flight between Canada and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago