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Cheap flights from Toronto to Chicago from $123

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 7/14. 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
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Tue 6/25
Tue 7/2

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Easily compare round-trip flights from Toronto 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 Toronto to Chicago by changing tabs
Porter Airlines
Jul 17
YTZ9:20 amToronto Island
1h 47m
MDW10:07 amChicago Midway
Jul 19
MDW8:00 amChicago Midway
1h 42m
YTZ10:42 amToronto Island
American Airlines
Aug 16
YYZ6:25 pmToronto Pearson Intl
1h 54m
ORD7:19 pmChicago O'Hare Intl
Aug 18
ORD8:28 amChicago O'Hare Intl
1h 49m
YYZ11:17 amToronto Pearson Intl
Multiple Airlines
Jul 3
YYZ7:00 amToronto Pearson Intl
1h 57m
ORD7:57 amChicago O'Hare Intl
Jul 7
ORD6:00 amChicago O'Hare Intl
1h 48m
YYZ8:48 amToronto Pearson Intl
Air Canada
Jul 17
YTZ8:20 amToronto Island
5h 53m
1 stop
ORD1:13 pmChicago O'Hare Intl
Jul 24
ORD1:55 pmChicago O'Hare Intl
5h 49m
1 stop
YTZ8:44 pmToronto Island
Air Transat
Jul 2
YTZ9:20 amToronto Island
1h 47m
MDW10:07 amChicago Midway
Jul 3
MDW8:00 amChicago Midway
1h 42m
YTZ10:42 amToronto Island
United Airlines
Jul 4
YYZ6:15 amToronto Pearson Intl
13h 40m
1 stop
ORD6:55 pmChicago O'Hare Intl
Jul 7
ORD6:00 amChicago O'Hare Intl
1h 48m
YYZ8:48 amToronto Pearson Intl

Find the cheapest one-way flights from Toronto to Chicago

If you're looking for one-way flights from Toronto to Chicago, view some of our deals below provided by American Airlines and Porter Airlines
Porter Airlines
Jul 14
YTZ10:30 amToronto Island
1h 47m
MDW11:17 amChicago Midway
Multiple Airlines
Jul 23
YYZ6:30 amToronto Pearson Intl
16h 35m
1 stop
ORD10:05 pmChicago O'Hare Intl
American Airlines
Jul 2
YYZ1:20 pmToronto Pearson Intl
1h 55m
ORD2:15 pmChicago O'Hare Intl

Find the cheapest direct flights from Toronto to Chicago

Porter Airlines
Jul 7
YTZ10:30 amToronto Island
1h 47m
MDW11:17 amChicago Midway
Jul 14
MDW8:40 amChicago Midway
1h 42m
YTZ11:22 amToronto Island
American Airlines
Aug 16
YYZ6:25 pmToronto Pearson Intl
1h 54m
ORD7:19 pmChicago O'Hare Intl
Aug 18
ORD8:28 amChicago O'Hare Intl
1h 49m
YYZ11:17 amToronto Pearson Intl
Multiple Airlines
Jul 3
YYZ7:00 amToronto Pearson Intl
1h 57m
ORD7:57 amChicago O'Hare Intl
Jul 7
ORD6:00 amChicago O'Hare Intl
1h 48m
YYZ8:48 amToronto Pearson Intl
Lufthansa
Jul 26
YYZ7:00 amToronto Pearson Intl
1h 57m
ORD7:57 amChicago O'Hare Intl
Jul 28
ORD6:00 amChicago O'Hare Intl
1h 48m
YYZ8:48 amToronto Pearson Intl
Air Canada
Jul 19
YYZ7:40 amToronto Pearson Intl
1h 56m
ORD8:36 amChicago O'Hare Intl
Jul 23
ORD6:00 pmChicago O'Hare Intl
1h 43m
YYZ8:43 pmToronto Pearson Intl
Air Transat
Jul 5
YTZ3:30 pmToronto Island
1h 47m
MDW4:17 pmChicago Midway
Jul 7
MDW8:40 amChicago Midway
1h 42m
YTZ11:22 amToronto Island

Search last-minute flights to Chicago from Toronto

Find and compare round-trip flight prices for your last-minute flight from Toronto to Chicago
Air Canada
Jul 3
YYZ7:47 amToronto Pearson Intl
1h 56m
ORD8:43 amChicago O'Hare Intl
Jul 7
ORD6:00 amChicago O'Hare Intl
1h 48m
YYZ8:48 amToronto Pearson Intl
Porter Airlines
Jun 29
YTZ6:15 pmToronto Island
1h 47m
MDW7:02 pmChicago Midway
Jul 3
MDW11:05 amChicago Midway
1h 42m
YTZ1:47 pmToronto Island
United Airlines
Jul 4
YYZ2:45 pmToronto Pearson Intl
5h 10m
1 stop
ORD6:55 pmChicago O'Hare Intl
Jul 7
ORD6:00 amChicago O'Hare Intl
1h 48m
YYZ8:48 amToronto Pearson Intl
American Airlines
Jun 22
YYZ1:20 pmToronto Pearson Intl
1h 55m
ORD2:15 pmChicago O'Hare Intl
Jun 27
ORD5:30 amChicago O'Hare Intl
4h 43m
1 stop
YYZ11:13 amToronto Pearson Intl
WestJet
Jul 4
YYZ6:04 amToronto Pearson Intl
15h 59m
1 stop
ORD9:03 pmChicago O'Hare Intl
Jul 7
ORD7:30 pmChicago O'Hare Intl
12h 20m
1 stop
YYZ8:50 amToronto Pearson Intl
Air Transat
Jun 26
YTZ9:20 amToronto Island
1h 47m
MDW10:07 amChicago Midway
Jul 8
MDW8:00 amChicago Midway
1h 42m
YTZ10:42 amToronto Island

American Airlines flights from Toronto to Chicago

Our best American Airlines deals on Toronto to Chicago flight tickets
American Airlines
Aug 16
YYZ6:25 pmToronto Pearson Intl
1h 54m
ORD7:19 pmChicago O'Hare Intl
Aug 18
ORD8:28 amChicago O'Hare Intl
1h 49m
YYZ11:17 amToronto Pearson Intl
American Airlines
Oct 9
YYZ6:48 amToronto Pearson Intl
1h 57m
ORD7:45 amChicago O'Hare Intl
Oct 13
ORD9:50 amChicago O'Hare Intl
1h 39m
YYZ12:29 pmToronto Pearson Intl
American Airlines
Jul 2
YYZ11:55 amToronto Pearson Intl
1h 55m
ORD12:50 pmChicago O'Hare Intl
Jul 10
ORD11:50 amChicago O'Hare Intl
5h 48m
1 stop
YYZ6:38 pmToronto Pearson Intl

WestJet flights from Toronto to Chicago

Our best WestJet deals on Toronto to Chicago flight tickets
WestJet
Jul 4
YYZ6:04 amToronto Pearson Intl
15h 59m
1 stop
ORD9:03 pmChicago O'Hare Intl
Jul 7
ORD7:30 pmChicago O'Hare Intl
12h 20m
1 stop
YYZ8:50 amToronto Pearson Intl
WestJet
Aug 2
YYZ11:35 amToronto Pearson Intl
10h 42m
1 stop
ORD9:17 pmChicago O'Hare Intl
Aug 5
ORD7:20 pmChicago O'Hare Intl
20h 48m
1 stop
YYZ5:08 pmToronto Pearson Intl
WestJet
Aug 17
YYZ7:45 amToronto Pearson Intl
4h 59m
1 stop
MDW11:44 amChicago Midway
Aug 20
MDW6:11 amChicago Midway
14h 47m
1 stop
YYZ9:58 pmToronto Pearson Intl

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 cheapest month to fly from Toronto to Chicago?

April. The cheapest time of year to fly to Chicago from Toronto is April. Most expensive is September

What is the cheapest day to depart Toronto for Chicago?

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

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

In the evening. Toronto to Chicago flights are approximately 12% more expensive in the afternoon than in the evening

What is the cheapest airline that flies to Chicago from Toronto?

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

What is the cheapest Toronto to Chicago flight route?

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

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

37 days before. The cheapest time to buy a flight from Toronto to Chicago is approximately 37 days to departure

How many flights depart from Toronto to Chicago on average per day?

The number of flights available between Toronto and Chicago is 54 per day as of June 2024. The most frequent departure time is 12:00PM, with 57% of daily flights leaving in the afternoon.

How many flights depart from Toronto to Chicago on average per week?

As of June 2024, 379 flights take off from Toronto and land in Chicago each week. The most common flight departure day for this route is Friday, with 17% of weekly flights taking off on this day.

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.

Can stopping save me money on Toronto to Chicago flights?

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

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

$123

Fastest flight time

1h 47m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Toronto in the past 72 hours is $123. The best round-trip flight deal from Toronto to Chicago found on momondo in the last 72 hours is $205.
The fastest flight from Toronto to Chicago takes 1h 47m
Direct flights go from Toronto to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Toronto to Chicago by plane?

    There are 435.3 mi between Toronto and Chicago. Flights usually cover this in 1h 47m, 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.


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 $206Free CancellationRating
7.5
371 reviews
Search Porter Airlines flights
Air CanadaPriceFrom $211Free CancellationRating
7.0
7,126 reviews
Search Air Canada flights
United AirlinesPriceFrom $227Free CancellationRating
7.4
10,000 reviews
Search United Airlines flights
American AirlinesPriceFrom $242Free CancellationRating
7.3
10,000 reviews
Search American Airlines flights
  • Porter Airlines Flights From Toronto to Chicago

    Porter Airlines flies from Toronto to Chicago around 14 times per week, with 371 momondo users rating the airline 7.5/10. The cheapest Porter Airlines deal from Toronto to Chicago in the last 72 hours was $206 (round-trip), much lower than the average airfare cost of $286 for Porter Airlines flights on this route.

  • United Airlines Flights From Toronto to Chicago

    United Airlines (7.4/10 from 10,000 reviews) operates around 67 flights from Toronto to Chicago in any given week. The average United Airlines airfare for this route is around $348, 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.


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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From?
To?
Tue 6/25
Tue 7/2
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Find better results for your trip to the United States

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