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Cheap flights from Chicago to Toronto from $69

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 9/3. 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 (CHI-YTZ)

Cheap round-trip flights

Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$192Porter Airlines
Find Deal
Fri, Sep 26 - Sun, Sep 28
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$193Porter Airlines
Find Deal
Mon, Sep 15 - Thu, Sep 18
Porter Airlines Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$195Porter Airlines
Find Deal
Fri, Sep 12 - Thu, Sep 18
Porter Airlines Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$196Porter Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
Air Canada Logo
8:40 am - 4:45 pmORD-YTZ
7h 05m1 stop
Air Canada Logo
3:25 pm - 8:22 pmYTZ-ORD
5h 57m1 stop
$209Air Canada
Find Deal
Mon, Sep 29 - Mon, Oct 6
Air Canada Logo
8:40 am - 4:45 pmORD-YTZ
7h 05m1 stop
Air Canada Logo
10:20 am - 8:22 pmYTZ-ORD
11h 02m2 stops
$210Air Canada
Find Deal
Mon, Sep 29 - Mon, Oct 6
Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$224
Find Deal
Tue, Sep 30 - Tue, Oct 7
Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$225
Find Deal
Fri, Sep 5 - Sun, Sep 7
Air Transat Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$246Air Transat
Find Deal
Thu, Sep 25 - Sat, Oct 25
Air Transat Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$249Air Transat
Find Deal
Thu, Sep 25 - Thu, Oct 2

Porter Airlines flights from Chicago to Toronto Island Airport

Our best Porter Airlines deals on Chicago to Toronto Island Airport flight tickets
Porter Airlines
Sep 26
MDW9:35 amChicago Midway
1h 42m
YTZ12:17 pmToronto Island
Sep 28
YTZ7:50 amToronto Island
1h 49m
MDW8:39 amChicago Midway
$192
Find similar
Porter Airlines
Sep 15
MDW9:35 amChicago Midway
1h 42m
YTZ12:17 pmToronto Island
Sep 18
YTZ3:35 pmToronto Island
1h 49m
MDW4:24 pmChicago Midway
$193
Find similar
Porter Airlines
Sep 12
MDW5:20 pmChicago Midway
1h 42m
YTZ8:02 pmToronto Island
Sep 18
YTZ3:35 pmToronto Island
1h 49m
MDW4:24 pmChicago Midway
$195
Find similar

Air Canada flights from Chicago to Toronto Island Airport

Our best Air Canada deals on Chicago to Toronto Island Airport flight tickets
Air Canada
Sep 29
ORD8:40 amChicago O'Hare Intl
7h 05m
1 stop
YTZ4:45 pmToronto Island
Oct 6
YTZ3:25 pmToronto Island
5h 57m
1 stop
ORD8:22 pmChicago O'Hare Intl
$209
Find similar
Air Canada
Sep 29
ORD8:40 amChicago O'Hare Intl
7h 05m
1 stop
YTZ4:45 pmToronto Island
Oct 6
YTZ10:20 amToronto Island
11h 02m
2 stops
ORD8:22 pmChicago O'Hare Intl
$210
Find similar
Air Canada
Sep 30
ORD8:40 amChicago O'Hare Intl
5h 05m
1 stop
YTZ2:45 pmToronto Island
Oct 7
YTZ3:25 pmToronto Island
5h 46m
1 stop
ORD8:11 pmChicago O'Hare Intl
$216
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Toronto Island Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 17, 2025.
Use the filters below to find and compare flights from Chicago to Toronto Island Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 9/26

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 9/28

7:50 am-8:39 am

Nonstop1h 49m

$192

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 9/15

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Thu 9/18

3:35 pm-4:24 pm

Nonstop1h 49m

$193

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 9/12

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Thu 9/18

3:35 pm-4:24 pm

Nonstop1h 49m

$195

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 10/2

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Sun 10/5

7:50 am-8:39 am

Nonstop1h 49m

$196

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Mon 9/29

8:40 am-4:45 pm

1 stop7h 05m

Toronto Island

Mon 10/6

3:25 pm-8:22 pm

1 stop5h 57m

$209

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Mon 9/29

8:40 am-4:45 pm

1 stop7h 05m

Toronto Island

Mon 10/6

10:20 am-8:22 pm

2 stops11h 02m

$210

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 9/30

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Tue 10/7

7:50 am-8:39 am

Nonstop1h 49m

$224

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 9/5

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Sun 9/7

7:50 am-8:39 am

Nonstop1h 49m

$225

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 9/25

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sat 10/25

7:50 am-8:39 am

Nonstop1h 49m

$246

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 9/25

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Thu 10/2

7:50 am-8:39 am

Nonstop1h 49m

$249

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Toronto from

How to get the cheapest flight ticket from Chicago to Toronto Island Airport

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 Toronto Island Airport?

If you aren’t able to travel during the month of July, then book flights to Toronto Island Airport from Chicago during October instead. Flights to Toronto Island Airport in October, while not as cheap as those in July, still average around $197.

What is the cheapest day to depart on your flight to Toronto Island Airport?

The cheapest day to depart on your flight to Toronto Island Airport is on a Saturday when prices can be found for as low as $272. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $345. These prices are subject to change though, so be sure to set up a Price Alert for flights to Toronto Island Airport.

What is the cheapest time of day to depart on your flight to Toronto Island Airport?

Our data shows that the cheapest Chicago to Toronto Island Airport flights are usually those with departure times in the afternoon. Our users have found flights to Toronto Island Airport in the afternoon for as low as $277. In contrast, the most expensive time of day to depart to Toronto Island Airport is in the evening when prices are around $311.

What is the cheapest Chicago to Toronto Island flight route?

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

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

There are 3 cabin classes available to choose from on Chicago to Toronto Island 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 Island Airport flights?

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

When to book flights from Chicago to Toronto Island Airport

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

Cheap Chicago to Toronto Island Airport (CHI to YTZ) flight deals and tips

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

Best Price Found

$69

Fastest flight time

1h 40m

Direct flights

Every day
The best one-way flight to Toronto Island Airport from Chicago in the past 72 hours is $69. The best round-trip flight deal from Chicago to Toronto Island Airport found on momondo in the last 72 hours is $192.
The fastest flight from Chicago to Toronto Island Airport takes 1h 40m
Direct flights go from Chicago to Toronto Island Airport every day.
Search flight deals

  • How far is Chicago to Toronto Island by plane?

    There are 434.2 mi between Chicago and Toronto Island. In terms of flight time, this usually takes a little over 1h 42m.

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

    Prices for flights from Chicago to Toronto Island Airport refresh daily.

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

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

    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 Island Airport.

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

    The travel and health documents required for your trip to Toronto Island Airport 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 Island Airport. 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 Island Airport?

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

Best airlines flying from Chicago to Toronto Island Airport

Compare and see reviews for airlines that fly from Chicago to Toronto Island Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom $187Free CancellationRating
8.0
332 reviews
Search Porter Airlines flights

  • Porter Airlines Flights From Chicago to Toronto Island Airport

    Porter Airlines operates around 13 flights from Chicago to Toronto Island Airport every week. The average price of these flights found in the last 72 hours has been $271, but momondo users have found Porter Airlines deals from Chicago to Toronto Island Airport from as low as $187 round-trip. Porter Airlines has been scored 8.0/10 in 332 reviews.

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Toronto. Millions of users trust and use momondo every year so you are in good hands.

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?

Price alerts on flights to Toronto from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Toronto Island Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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