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Cheap flights from Canada to Chicago from $119

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 5/1. 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
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Tue 4/2
Tue 4/9

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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

$119

Fastest flight time

1h 47m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Canada in the past 72 hours is $119. The best round-trip flight deal from Canada to Chicago found on momondo in the last 72 hours is $204.
The fastest flight from Canada to Chicago takes 1h 47m
Direct flights go from Canada to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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 airline that flies to Chicago from Canada?

WestJet. Air Canada, American Airlines, and Delta are the most popular carriers operating from Canada to Chicago

What is the cheapest Canada to Chicago flight route?

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

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?

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

Easily compare round-trip flights from Canada to Chicago

Below you can see the best fares for your round-trip flight route over the next six months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Canada to Chicago by changing tabs
Porter Airlines
Apr 26
YTZ8:50 pmToronto Island
1h 47m
MDW9:37 pmChicago Midway
May 3
MDW8:00 amChicago Midway
1h 42m
YTZ10:42 amToronto Island
Air Canada
May 5
YYZ9:00 amToronto Pearson Intl
1h 54m
ORD9:54 amChicago O'Hare Intl
May 11
ORD6:00 amChicago O'Hare Intl
1h 45m
YYZ8:45 amToronto Pearson Intl
American Airlines
Apr 17
YYZ6:30 amToronto Pearson Intl
1h 55m
ORD7:25 amChicago O'Hare Intl
Apr 24
ORD9:55 amChicago O'Hare Intl
1h 40m
YYZ12:35 pmToronto Pearson Intl
United Airlines
May 7
YYZ12:00 pmToronto Pearson Intl
1h 54m
ORD12:54 pmChicago O'Hare Intl
May 14
ORD1:00 pmChicago O'Hare Intl
1h 43m
YYZ3:43 pmToronto Pearson Intl
Multiple Airlines
Jul 4
YYZ12:00 pmToronto Pearson Intl
1h 54m
ORD12:54 pmChicago O'Hare Intl
Jul 7
ORD6:00 amChicago O'Hare Intl
1h 48m
YYZ8:48 amToronto Pearson Intl
Delta
Apr 17
YYZ5:12 pmToronto Pearson Intl
6h 09m
1 stop
ORD10:21 pmChicago O'Hare Intl
Apr 20
ORD1:35 pmChicago O'Hare Intl
8h 11m
1 stop
YYZ10:46 pmToronto Pearson Intl

Find the cheapest one-way flights from Canada to Chicago

If you're looking for one-way flights from Canada to Chicago, view some of our deals below provided by Air Canada, American Airlines and Porter Airlines
Porter Airlines
May 1
YTZ9:20 amToronto Island
1h 47m
MDW10:07 amChicago Midway
Air Canada
Apr 27
YYZ8:00 amToronto Pearson Intl
1h 54m
ORD8:54 amChicago O'Hare Intl
American Airlines
Jun 5
YYC1:30 pmCalgary
3h 25m
ORD5:55 pmChicago O'Hare Intl

Search last-minute flights to Chicago from Canada

Find and compare round-trip flight prices for your last-minute flight from Canada to Chicago
Porter Airlines
Apr 6
YTZ10:45 amToronto Island
1h 47m
MDW11:32 amChicago Midway
Apr 17
MDW8:00 amChicago Midway
1h 42m
YTZ10:42 amToronto Island
Delta
Apr 10
YYC2:10 pmCalgary
9h 49m
1 stop
ORD12:59 amChicago O'Hare Intl
Apr 17
ORD12:15 pmChicago O'Hare Intl
9h 41m
1 stop
YYC8:56 pmCalgary
American Airlines
Apr 6
YYZ11:55 amToronto Pearson Intl
1h 55m
ORD12:50 pmChicago O'Hare Intl
Apr 17
ORD1:20 pmChicago O'Hare Intl
8h 00m
1 stop
YYZ10:20 pmToronto Pearson Intl
Multiple Airlines
Apr 10
YTZ2:30 pmToronto Island
19h 53m
2 stops
ORD9:23 amChicago O'Hare Intl
Apr 12
ORD5:00 amChicago O'Hare Intl
16h 09m
2 stops
YTZ10:09 pmToronto Island
Air Canada
Apr 3
YYZ6:35 pmToronto Pearson Intl
1h 54m
ORD7:29 pmChicago O'Hare Intl
Apr 10
ORD9:40 amChicago O'Hare Intl
1h 45m
YYZ12:25 pmToronto Pearson Intl
WestJet
Apr 4
YYZ6:00 amToronto Pearson Intl
4h 31m
1 stop
ORD9:31 amChicago O'Hare Intl
Apr 21
ORD6:20 amChicago O'Hare Intl
4h 11m
1 stop
YYZ11:31 amToronto Pearson Intl

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
American AirlinesPriceFrom $189Free CancellationRating
7.3
15,202 reviews
Search American Airlines flights
WestJetPriceFrom $203Free CancellationRating
7.5
3,035 reviews
Search WestJet flights
Porter AirlinesPriceFrom $205Free CancellationRating
7.4
451 reviews
Search Porter Airlines flights
Air CanadaPriceFrom $211Free CancellationRating
7.0
6,743 reviews
Search Air Canada flights
United AirlinesPriceFrom $223Free CancellationRating
7.4
11,481 reviews
Search United Airlines flights
DeltaPriceFrom $334Free CancellationRating
8.0
11,418 reviews
Search Delta flights

WestJet flights from Canada to Chicago

Our best WestJet deals on Canada to Chicago flight tickets
WestJet
Jun 6
YYZ6:04 pmToronto Pearson Intl
6h 51m
1 stop
ORD11:55 pmChicago O'Hare Intl
Jun 8
ORD5:45 pmChicago O'Hare Intl
4h 05m
1 stop
YYZ10:50 pmToronto Pearson Intl
WestJet
Apr 20
YYZ6:15 amToronto Pearson Intl
9h 00m
1 stop
ORD2:15 pmChicago O'Hare Intl
Apr 21
ORD6:20 amChicago O'Hare Intl
4h 11m
1 stop
YYZ11:31 amToronto Pearson Intl
WestJet
Jun 13
YYZ1:25 pmToronto Pearson Intl
11h 34m
1 stop
ORD11:59 pmChicago O'Hare Intl
Jun 16
ORD10:20 amChicago O'Hare Intl
21h 30m
1 stop
YYZ8:50 amToronto Pearson Intl

United Airlines flights from Canada to Chicago

Our best United Airlines deals on Canada to Chicago flight tickets
United Airlines
May 7
YYZ12:00 pmToronto Pearson Intl
1h 54m
ORD12:54 pmChicago O'Hare Intl
May 14
ORD1:00 pmChicago O'Hare Intl
1h 43m
YYZ3:43 pmToronto Pearson Intl
United Airlines
Apr 18
YUL6:15 amMontreal Pierre Elliott Trudeau Intl
2h 46m
ORD8:01 amChicago O'Hare Intl
Apr 22
ORD7:20 amChicago O'Hare Intl
2h 09m
YUL10:29 amMontreal Pierre Elliott Trudeau Intl
United Airlines
Apr 24
YUL6:15 amMontreal Pierre Elliott Trudeau Intl
2h 46m
ORD8:01 amChicago O'Hare Intl
May 1
ORD9:07 pmChicago O'Hare Intl
13h 38m
1 stop
YUL11:45 amMontreal Pierre Elliott Trudeau Intl

  • 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.


Alternative routes for Canada to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Toronto to Chicago Flights
Fastest flight time1h 47m
Cheapest price$204
Vancouver to Chicago Flights
Fastest flight time4h 01m
Cheapest price$282
Montreal to Chicago Flights
Fastest flight time4h 02m
Cheapest price$214
Calgary to Chicago Flights
Fastest flight time3h 25m
Cheapest price$278
Winnipeg to Chicago Flights
Fastest flight time2h 21m
Cheapest price$338
Toronto to St. Louis Flights
Fastest flight time2h 06m
Cheapest price$422
Ottawa to Chicago Flights
Fastest flight time3h 37m
Cheapest price$235
Québec City to Chicago Flights
Fastest flight time5h 27m
Cheapest price$336
Abbotsford to Chicago Flights
Fastest flight time9h 07m
Cheapest price$457
Edmonton to Chicago Flights
Fastest flight time6h 18m
Cheapest price$370
Montreal to St. Louis Flights
Fastest flight time2h 35m
Cheapest price$406
Victoria to Chicago Flights
Fastest flight time7h 11m
Cheapest price$444

Similar Canada to Chicago flights

Flexible with your destination? Broaden your search and find flights similar to your Canada to Chicago route

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.


An easier way to manage your Chicago trip

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Airports listed have a maximum distance of 78.5 mi from Chicago


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