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Cheap flights from Chicago to Toronto from $105

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Toronto departing on 12/24. 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 Chicago to Toronto

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Toronto that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Toronto.

Cheap last minute flights

Planning a quick getaway from Chicago to Toronto? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Toronto, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Toronto

Find recent round-trip train or bus tickets from Chicago to Toronto.

All round-trip flight deals to Toronto

The cheapest plane tickets to Toronto found on KAYAK recently.
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
$253Porter Airlines
Find Deal
Tue, Dec 24 - Tue, Dec 31
11:25 am - 2:07 pmMDW-YTZ
1h 42mnonstop
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$254Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
12:52 pm - 3:45 pmORD-YYZ
1h 53mnonstop
8:00 am - 8:57 amYYZ-ORD
1h 57mnonstop
$279Air Canada
Find Deal
Wed, Dec 18 - Wed, Dec 25
12:52 pm - 3:45 pmORD-YYZ
1h 53mnonstop
8:00 am - 8:57 amYYZ-ORD
1h 57mnonstop
$280Air Canada
Find Deal
Wed, Dec 18 - Wed, Dec 25
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
12:20 pm - 6:36 pmYYZ-ORD
7h 16m1 stop
$285United Airlines
Find Deal
Thu, Dec 12 - Thu, Dec 12
4:00 pm - 8:34 amORD-YYZ
15h 34m1 stop
12:20 pm - 1:11 pmYYZ-ORD
1h 51mnonstop
$289United Airlines
Find Deal
Tue, Dec 10 - Wed, Dec 11
9:49 am - 12:30 pmORD-YYZ
1h 41mnonstop
10:59 am - 10:05 pmYYZ-ORD
12h 06m1 stop
$332American Airlines
Find Deal
Wed, Dec 18 - Wed, Dec 25
8:02 am - 4:40 pmORD-YYZ
7h 38m1 stop
7:12 pm - 12:14 amYYZ-ORD
6h 02m1 stop
$336American Airlines
Find Deal
Thu, Dec 12 - Thu, Dec 12
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$351Air Transat
Find Deal
Fri, Jan 31 - Sun, Feb 2
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$490Air Transat
Find Deal
Tue, Apr 15 - Fri, Apr 18
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$105Porter Airlines
Find Deal
Tue, Dec 24
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$110Porter Airlines
Find Deal
Tue, Dec 24
6:38 pm - 9:25 pmORD-YYZ
1h 47mnonstop
$127United Airlines
Find Deal
Fri, Dec 13
7:20 am - 1:41 pmORD-YYZ
5h 21m1 stop
$132Air Canada
Find Deal
Tue, Dec 17
3:00 pm - 5:40 pmORD-YYZ
1h 40mnonstop
$136American Airlines
Find Deal
Thu, Dec 19
7:25 am - 8:25 pmORD-YYZ
12h 00m1 stop
$137United Airlines
Find Deal
Tue, Dec 24
1:55 pm - 8:25 pmORD-YYZ
5h 30m1 stop
$139Air Canada
Find Deal
Wed, Feb 12
6:00 am - 11:53 amORD-YYZ
4h 53m1 stop
$153American Airlines
Find Deal
Wed, Jan 1
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$161Air Transat
Find Deal
Sat, Dec 21
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$165Air Transat
Find Deal
Sun, Jan 5
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
11:00 am - 11:59 amYYZ-ORD
1h 59mnonstop
$442Air Canada
Find Deal
Mon, Nov 25 - Tue, Dec 3
8:57 am - 2:18 pmORD-YYZ
4h 21m1 stop
3:30 pm - 4:30 pmYYZ-ORD
2h 00mnonstop
$452United Airlines
Find Deal
Mon, Nov 25 - Tue, Dec 3
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$484Porter Airlines
Find Deal
Mon, Nov 25 - Fri, Nov 29
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
$491Porter Airlines
Find Deal
Mon, Nov 25 - Tue, Nov 26
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
$501Porter Airlines
Find Deal
Sun, Nov 24 - Tue, Nov 26
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
3:30 pm - 4:30 pmYYZ-ORD
2h 00mnonstop
$524Air Canada
Find Deal
Sun, Nov 24 - Tue, Dec 3
6:34 pm - 9:29 pmORD-YYZ
1h 55mnonstop
11:37 am - 12:37 pmYYZ-ORD
2h 00mnonstop
$568American Airlines
Find Deal
Sat, Nov 23 - Fri, Nov 29
6:34 pm - 9:29 pmORD-YYZ
1h 55mnonstop
11:37 am - 12:37 pmYYZ-ORD
2h 00mnonstop
$574American Airlines
Find Deal
Sun, Nov 24 - Mon, Dec 2
9:10 pm - 12:06 pmORD-YYZ
13h 56m1 stop
6:52 am - 8:05 amYYZ-ORD
2h 13mnonstop
$604United Airlines
Find Deal
Sat, Nov 23 - Sat, Nov 30
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
$1,194Air Transat
Find Deal
Thu, Nov 21 - Fri, Nov 22
11:25 am - 2:07 pmMDW-YTZ
1h 42mnonstop
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
$252Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
$253Porter Airlines
Find Deal
Tue, Dec 24 - Tue, Dec 31
12:52 pm - 3:45 pmORD-YYZ
1h 53mnonstop
8:00 am - 8:57 amYYZ-ORD
1h 57mnonstop
$279Air Canada
Find Deal
Wed, Dec 18 - Wed, Dec 25
12:52 pm - 3:45 pmORD-YYZ
1h 53mnonstop
8:00 am - 8:57 amYYZ-ORD
1h 57mnonstop
$280Air Canada
Find Deal
Wed, Dec 18 - Wed, Dec 25
12:52 pm - 3:45 pmORD-YYZ
1h 53mnonstop
8:00 am - 8:57 amYYZ-ORD
1h 57mnonstop
$302United Airlines
Find Deal
Wed, Dec 18 - Thu, Dec 26
9:13 pm - 11:59 pmORD-YYZ
1h 46mnonstop
9:00 pm - 10:13 pmYYZ-ORD
2h 13mnonstop
$318United Airlines
Find Deal
Tue, Dec 24 - Mon, Jan 6
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$351Air Transat
Find Deal
Fri, Jan 31 - Sun, Feb 2
6:30 pm - 9:25 pmORD-YYZ
1h 55mnonstop
11:40 am - 12:40 pmYYZ-ORD
2h 00mnonstop
$418American Airlines
Find Deal
Sun, Dec 22 - Mon, Dec 30
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$490Air Transat
Find Deal
Tue, Apr 15 - Fri, Apr 18
6:35 pm - 9:20 pmORD-YYZ
1h 45mnonstop
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
$517American Airlines
Find Deal
Sat, Jan 11 - Sun, Jan 12

Air Canada flights from Chicago to Toronto

Our best Air Canada deals on Chicago to Toronto flight tickets
Air Canada
Dec 18
ORD12:52 pmChicago O'Hare Intl
1h 53m
YYZ3:45 pmToronto Pearson Intl
Dec 25
YYZ8:00 amToronto Pearson Intl
1h 57m
ORD8:57 amChicago O'Hare Intl
Air Canada
Dec 18
ORD12:52 pmChicago O'Hare Intl
1h 53m
YYZ3:45 pmToronto Pearson Intl
Dec 25
YYZ8:00 amToronto Pearson Intl
1h 57m
ORD8:57 amChicago O'Hare Intl
Air Canada
Dec 12
ORD7:20 amChicago O'Hare Intl
6h 30m
1 stop
YTZ2:50 pmToronto Island
Dec 15
YTZ8:50 amToronto Island
5h 08m
1 stop
ORD12:58 pmChicago O'Hare Intl

American Airlines flights from Chicago to Toronto

Our best American Airlines deals on Chicago to Toronto flight tickets
American Airlines
Dec 18
ORD9:49 amChicago O'Hare Intl
1h 41m
YYZ12:30 pmToronto Pearson Intl
Dec 25
YYZ10:59 amToronto Pearson Intl
12h 06m
1 stop
ORD10:05 pmChicago O'Hare Intl
American Airlines
Dec 12
ORD8:02 amChicago O'Hare Intl
7h 38m
1 stop
YYZ4:40 pmToronto Pearson Intl
Dec 12
YYZ7:12 pmToronto Pearson Intl
6h 02m
1 stop
ORD12:14 amChicago O'Hare Intl
American Airlines
Dec 4
ORD8:11 amChicago O'Hare Intl
1h 40m
YYZ10:51 amToronto Pearson Intl
Dec 4
YYZ1:54 pmToronto Pearson Intl
7h 38m
1 stop
ORD8:32 pmChicago O'Hare Intl

See travel insights to Toronto from

How to get the cheapest flight ticket from Chicago to Toronto

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 from Chicago to Toronto?

January. The cheapest time of year to fly to Toronto from Chicago is January. Most expensive is November

What is the cheapest day to depart Chicago for Toronto?

Friday. The cheapest day of the week is typically Friday. The most expensive is typically Sunday

When is the cheapest time to fly from Chicago to Toronto?

In the morning. Chicago to Toronto flights are approximately 8% more expensive at noon than in the morning

What is the cheapest Chicago to Toronto flight route?

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

How far in advance should you book Chicago to Toronto flights?

39 days before. The cheapest time to buy a flight from Chicago to Toronto is approximately 39 days to departure

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

There are 2 cabin classes available to choose from on Chicago to Toronto 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 Chicago to Toronto flights?

You could potentially save up to 6% on your flight if you consider stops on a Chicago to Toronto flight.

How have Chicago to Toronto flight prices changed over time?

As of November 2024, prices for Chicago to Toronto flights are approximately 9% cheaper when compared to flights at the same time last year.

What is the typical price of a round-trip flight between Chicago and Toronto?


When to book flights from Chicago to Toronto

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Toronto according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Toronto (CHI to YTO) flight deals and tips

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

Best Price Found

$105

Fastest flight time

1h 35m

Direct flights

Every day

Airports in Toronto

2 airports
The best one-way flight to Toronto from Chicago in the past 72 hours is $105. The best round-trip flight deal from Chicago to Toronto found on momondo in the last 72 hours is $253.
The fastest flight from Chicago to Toronto takes 1h 35m
Direct flights go from Chicago to Toronto every day.
There are 2 airports near Toronto: Toronto Pearson Intl (YYZ), Toronto Island (YTZ)

  • How far is Chicago to Toronto by plane?

    A flight from Chicago to Toronto will travel around 435.3 mi. Typically, this will take 1h 38m by plane in normal conditions.

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

    Prices for flights from Chicago to Toronto refresh daily.

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

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

    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 Chicago to Toronto.

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

    The travel and health documents required for your trip to Toronto can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Toronto. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago to Toronto?

  • What is the most popular airline from Chicago to Toronto?


Best airlines flying from Chicago to Toronto

Compare and see reviews for airlines that fly from Chicago to Toronto with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $121Free CancellationRating
7.0
8,237 reviews
Search Air Canada flights
Porter AirlinesPriceFrom $122Free CancellationRating
7.8
288 reviews
Search Porter Airlines flights
American AirlinesPriceFrom $122Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $145Free CancellationRating
7.4
9,171 reviews
Search United Airlines flights
  • Porter Airlines Flights From Chicago to Toronto

    Across 9 Porter Airlines flights from Chicago to Toronto this week, the average price was $233, with the best Porter Airlines deals starting from $122 round-trip. 288 users have rated Porter Airlines on momondo, with an average score of 7.8/10.

  • United Airlines Flights From Chicago to Toronto

    $145 is the best United Airlines flight deal from Chicago to Toronto found on momondo over the last 72 hours. The average United Airlines ticket price found was closer to $343, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 9,171 user reviews) flies into Toronto from Chicago 65 times in an average week so prices can vary.


Why use momondo?

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

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 Toronto from Chicago.

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

Yes. momondo allows you to filter the results for Chicago to Toronto flights to just show those with flexible booking policies.

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

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 Toronto from Chicago.

I’m not ready to book a flight from Chicago to Toronto right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Toronto now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Toronto and let you know when they change.


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Find better results for your trip to Canada

Fly into one of these airports located in Toronto

Airports listed have a maximum distance of 52.0 mi from Toronto