Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Toronto from $83

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 12/12. 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

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Toronto

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
11:00 am - 11:50 amYTZ-MDW
1h 50mnonstop
$188Porter Airlines
Find Deal
Wed, Nov 19 - Sat, Nov 22
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$190Porter Airlines
Find Deal
Wed, Nov 12 - Sun, Nov 16
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$191Porter Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$192Porter Airlines
Find Deal
Mon, Dec 8 - Thu, Dec 11
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$193Porter Airlines
Find Deal
Wed, Nov 12 - Thu, Nov 13
Multiple Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Multiple Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$219Multiple Airlines
Find Deal
Tue, Nov 11 - Fri, Nov 14
Multiple Airlines Logo
12:45 pm - 3:27 pmMDW-YTZ
1h 42mnonstop
Multiple Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$230Multiple Airlines
Find Deal
Sat, Feb 28 - Sun, Mar 1
Air Transat Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$244Air Transat
Find Deal
Mon, Dec 8 - Thu, Dec 11
Air Canada Logo
12:50 pm - 7:55 pmORD-YTZ
6h 05m1 stop
Air Canada Logo
10:30 am - 2:55 pmYTZ-ORD
5h 25m1 stop
$246Air Canada
Find Deal
Sat, Jan 17 - Sun, Jan 18
Air Canada Logo
12:50 pm - 7:55 pmORD-YTZ
6h 05m1 stop
Air Canada Logo
10:30 am - 8:10 pmYTZ-ORD
10h 40m1 stop
$276Air Canada
Find Deal
Sat, Dec 13 - Sat, Dec 20

Air Transat flights from Chicago to Toronto Island Airport

Our best Air Transat deals on Chicago to Toronto Island Airport flight tickets
Air Transat
Dec 8
MDW11:00 amChicago Midway
1h 42m
YTZ1:42 pmToronto Island
Dec 11
YTZ2:30 pmToronto Island
1h 50m
MDW3:20 pmChicago Midway
$244
Find similar
Air Transat
Nov 12
MDW11:00 amChicago Midway
1h 42m
YTZ1:42 pmToronto Island
Nov 22
YTZ11:00 amToronto Island
1h 50m
MDW11:50 amChicago Midway
$267
Find similar

Porter Airlines flights from Chicago to Toronto Island Airport

Our best Porter Airlines deals on Chicago to Toronto Island Airport flight tickets
Porter Airlines
Nov 19
MDW11:00 amChicago Midway
1h 42m
YTZ1:42 pmToronto Island
Nov 22
YTZ11:00 amToronto Island
1h 50m
MDW11:50 amChicago Midway
$188
Find similar
Porter Airlines
Nov 12
MDW11:00 amChicago Midway
1h 42m
YTZ1:42 pmToronto Island
Nov 16
YTZ9:15 amToronto Island
1h 50m
MDW10:05 amChicago Midway
$190
Find similar
Porter Airlines
Dec 5
MDW4:15 pmChicago Midway
1h 42m
YTZ6:57 pmToronto Island
Dec 7
YTZ9:15 amToronto Island
1h 50m
MDW10:05 amChicago Midway
$191
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 October 30, 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

Wed 11/19

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sat 11/22

11:00 am-11:50 am

Nonstop1h 50m

$188

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 11/12

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 11/16

9:15 am-10:05 am

Nonstop1h 50m

$190

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 12/5

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Sun 12/7

9:15 am-10:05 am

Nonstop1h 50m

$191

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 12/8

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Thu 12/11

9:15 am-10:05 am

Nonstop1h 50m

$192

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 11/12

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Thu 11/13

2:30 pm-3:20 pm

Nonstop1h 50m

$193

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 11/11

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Fri 11/14

2:30 pm-3:20 pm

Nonstop1h 50m

$219

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 2/28

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Sun 3/1

2:30 pm-3:20 pm

Nonstop1h 50m

$230

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 12/8

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Thu 12/11

2:30 pm-3:20 pm

Nonstop1h 50m

$244

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Sat 1/17

12:50 pm-7:55 pm

1 stop6h 05m

Toronto Island

Sun 1/18

10:30 am-2:55 pm

1 stop5h 25m

$246

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Sat 12/13

12:50 pm-7:55 pm

1 stop6h 05m

Toronto Island

Sat 12/20

10:30 am-8:10 pm

1 stop10h 40m

$276

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 September instead. Flights to Toronto Island Airport in September, 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 $256. 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 $334. 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 $268. 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

$186

Fastest flight time

1h 42m

Direct flights

Every day
The best one-way flight to Toronto Island Airport from Chicago in the past 72 hours is $186. The best round-trip flight deal from Chicago to Toronto Island Airport found on momondo in the last 72 hours is $257.
The fastest flight from Chicago to Toronto Island Airport takes 1h 42m
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 $185Free CancellationRating
8.0
384 reviews
Search Porter Airlines flights

  • Porter Airlines Flights From Chicago to Toronto Island Airport

    Porter Airlines operates around 6 flights from Chicago to Toronto Island Airport every week. The average price of these flights found in the last 72 hours has been $234, but momondo users have found Porter Airlines deals from Chicago to Toronto Island Airport from as low as $185 round-trip. Porter Airlines has been scored 8.0/10 in 384 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 11/29
Sat 12/6
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Toronto