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Cheap flights from Toronto to Chicago from $87

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto to Chicago departing on 6/9. 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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Find the cheapest flights from Toronto to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Toronto to Chicago.
Porter Airlines Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
$130Porter Airlines
Find Deal
Fri, May 23 - Mon, May 26
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
5:50 pm - 8:32 pmMDW-YTZ
1h 42mnonstop
$131Porter Airlines
Find Deal
Tue, Jun 3 - Sun, Jun 8
Air Canada Logo
8:15 am - 9:10 amYYZ-ORD
1h 55mnonstop
Air Canada Logo
10:00 am - 12:42 pmORD-YYZ
1h 42mnonstop
$149Air Canada
Find Deal
Sat, Jun 7 - Sat, Jun 14
Air Canada Logo
6:15 am - 9:52 amYYZ-ORD
4h 37m1 stop
Air Canada Logo
8:25 pm - 11:07 pmORD-YYZ
1h 42mnonstop
$152Air Canada
Find Deal
Sat, Jun 7 - Sat, Jun 14
United Airlines Logo
9:00 am - 9:59 amYYZ-ORD
1h 59mnonstop
United Airlines Logo
9:14 pm - 11:58 pmORD-YYZ
1h 44mnonstop
$161United Airlines
Find Deal
Mon, Jun 2 - Tue, Jun 10
Air Transat Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
Air Transat Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$187Air Transat
Find Deal
Sun, Jun 22 - Thu, Jun 26
United Airlines Logo
8:15 am - 9:09 amYYZ-ORD
1h 54mnonstop
United Airlines Logo
3:50 pm - 6:35 pmORD-YYZ
1h 45mnonstop
$193United Airlines
Find Deal
Sun, Jul 6 - Fri, Jul 18
Air Transat Logo
4:05 pm - 4:54 pmYTZ-MDW
1h 49mnonstop
Air Transat Logo
5:50 pm - 8:32 pmMDW-YTZ
1h 42mnonstop
$215Air Transat
Find Deal
Wed, May 7 - Sun, May 11
American Airlines Logo
6:20 pm - 7:15 pmYYZ-ORD
1h 55mnonstop
American Airlines Logo
8:11 am - 10:51 amORD-YYZ
1h 40mnonstop
$226American Airlines
Find Deal
Sat, May 17 - Sun, May 18
American Airlines Logo
1:15 pm - 2:10 pmYYZ-ORD
1h 55mnonstop
American Airlines Logo
5:00 am - 11:05 amORD-YYZ
5h 05m1 stop
$231American Airlines
Find Deal
Thu, May 22 - Mon, May 26

Air Canada flights from Toronto to Chicago

Our best Air Canada deals on Toronto to Chicago flight tickets
Air Canada
Jun 7
YYZ8:15 amToronto Pearson Intl
1h 55m
ORD9:10 amChicago O'Hare Intl
Jun 14
ORD10:00 amChicago O'Hare Intl
1h 42m
YYZ12:42 pmToronto Pearson Intl
Air Canada
Jun 7
YYZ6:15 amToronto Pearson Intl
4h 37m
1 stop
ORD9:52 amChicago O'Hare Intl
Jun 14
ORD8:25 pmChicago O'Hare Intl
1h 42m
YYZ11:07 pmToronto Pearson Intl
Air Canada
May 20
YTZ7:25 amToronto Island
5h 07m
1 stop
ORD11:32 amChicago O'Hare Intl
Jun 3
ORD10:56 amChicago O'Hare Intl
6h 41m
1 stop
YTZ6:37 pmToronto Island

American Airlines flights from Toronto to Chicago

Our best American Airlines deals on Toronto to Chicago flight tickets
American Airlines
May 6
YYZ6:20 pmToronto Pearson Intl
1h 55m
ORD7:15 pmChicago O'Hare Intl
May 8
ORD8:11 amChicago O'Hare Intl
1h 40m
YYZ10:51 amToronto Pearson Intl
American Airlines
May 17
YYZ6:20 pmToronto Pearson Intl
1h 55m
ORD7:15 pmChicago O'Hare Intl
May 18
ORD8:11 amChicago O'Hare Intl
1h 40m
YYZ10:51 amToronto Pearson Intl
American Airlines
May 22
YYZ1:15 pmToronto Pearson Intl
1h 55m
ORD2:10 pmChicago O'Hare Intl
May 26
ORD5:00 amChicago O'Hare Intl
5h 05m
1 stop
YYZ11:05 amToronto Pearson Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Toronto 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 typical price of a round-trip flight between Toronto and Chicago?

What is the cheapest month to fly to Chicago?

The month of March is, on average, the cheapest month to fly to Chicago from Toronto, with most prices found around $252. If you’re not able to fly to Chicago in March, then April is your next best option. Flight prices from Toronto to Chicago during April average around $252.

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 Friday when prices can be found for as low as $380. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Toronto to Chicago for around $666.

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 Toronto to Chicago during this time can be as low as $314. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $618.

What is the cheapest Toronto to Chicago flight route?

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

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

You are more likely to see cheaper flights to Chicago from Toronto when booking 16 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $303 when searching 16 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Toronto for as low as $263 on momondo.

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

There are 4 cabin classes available to choose from on Toronto to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Toronto to Chicago flight prices changed over time?

As of April 2025, prices for Toronto to Chicago flights are approximately 2% cheaper when compared to flights at the same time last year.

When to book flights from Toronto to Chicago

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

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

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

Best Price Found

$87

Fastest flight time

1h 49m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Toronto in the past 72 hours is $87. The best round-trip flight deal from Toronto to Chicago found on momondo in the last 72 hours is $130.
The fastest flight from Toronto to Chicago takes 1h 49m
Direct flights go from Toronto to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • Is flying the fastest way to get from Toronto to Chicago?

    The quickest way to travel this route is to take a flight from Toronto to Chicago, doing so can potentially save up to 11h 06m of travel time. While these options may take longer, booking a train from Toronto to Chicago or a bus from Toronto to Chicago may suit your needs if travel time is less of a factor in your decision making.

  • Is flying the cheapest way to get from Toronto to Chicago?

    The cheapest way is to get a bus from Toronto to Chicago, which can be as cheap as $101. A flight from Toronto to Chicago is more expensive than a bus, with prices starting at $130. A train from Toronto to Chicago is also an option, with an average price of $338.

  • How far is Toronto to Chicago by plane?

    There are 435.3 mi between Toronto and Chicago. Flights usually cover this in 1h 49m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Toronto to Chicago are updated daily.

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

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

    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 Toronto 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 Toronto to Chicago?

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


Best airlines flying from Toronto to Chicago

Compare and see reviews for airlines that fly from Toronto to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom $170Free CancellationRating
8.0
284 reviews
Search Porter Airlines flights
Air CanadaPriceFrom $196Free CancellationRating
7.0
9,189 reviews
Search Air Canada flights
United AirlinesPriceFrom $227Free CancellationRating
7.4
8,685 reviews
Search United Airlines flights
American AirlinesPriceFrom $228Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
  • Porter Airlines Flights From Toronto to Chicago

    Porter Airlines flies from Toronto to Chicago around 12 times per week, with 284 momondo users rating the airline 8.0/10. The cheapest Porter Airlines deal from Toronto to Chicago in the last 72 hours was $170 (round-trip), much lower than the average airfare cost of $261 for Porter Airlines flights on this route.

  • United Airlines Flights From Toronto to Chicago

    United Airlines (7.4/10 from 8,685 reviews) operates around 71 flights from Toronto to Chicago in any given week. The average United Airlines airfare for this route is around $311, with deals from around $227 rare but found on momondo. Referenced prices are for round-trip Toronto to Chicago flight searches in the last 72 hours.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
Saint John

Why use momondo?

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

It is quick and easy to find Toronto to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. momondo enables you to select and highlight flights to Chicago from Toronto with this policy.

How can momondo help me find flights from Toronto 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 Toronto.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Toronto and alert you when they change.


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1 adult
From?
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Mon 4/28
Mon 5/5

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