Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Toronto Island Airport to Chicago from C$ 188

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 Island Airport to Chicago departing on 20/10. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? 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 Toronto Island Airport to Chicago

Cheap round-trip flights

Multiple Airlines Logo
7:30 p.m. - 11:25 p.m.YTZ-MDW
4h 55m1 stop
Multiple Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 323Multiple Airlines
Find Deal
Tue, 14 Oct - Wed, 22 Oct
Porter Airlines Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 332Porter Airlines
Find Deal
Sat, 18 Oct - Sat, 25 Oct
Porter Airlines Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 333Porter Airlines
Find Deal
Thu, 16 Oct - Sun, 19 Oct
Porter Airlines Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 336Porter Airlines
Find Deal
Sat, 18 Oct - Mon, 20 Oct
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 337Porter Airlines
Find Deal
Thu, 6 Nov - Sun, 9 Nov
Multiple Airlines Logo
7:30 p.m. - 11:25 p.m.YTZ-MDW
4h 55m1 stop
Multiple Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 340Multiple Airlines
Find Deal
Tue, 14 Oct - Sun, 19 Oct
Air Canada Logo
3:25 p.m. - 8:17 p.m.YTZ-ORD
5h 52m1 stop
Air Canada Logo
8:40 a.m. - 2:45 p.m.ORD-YTZ
5h 05m1 stop
C$ 347Air Canada
Find Deal
Sat, 18 Oct - Sat, 25 Oct
Air Canada Logo
3:25 p.m. - 8:06 p.m.YTZ-ORD
5h 41m1 stop
Air Canada Logo
8:40 a.m. - 4:45 p.m.ORD-YTZ
7h 05m1 stop
C$ 366Air Canada
Find Deal
Sat, 4 Oct - Mon, 6 Oct
Air Transat Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Air Transat Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 388Air Transat
Find Deal
Sun, 5 Oct - Tue, 7 Oct
Air Transat Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Air Transat Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 399Air Transat
Find Deal
Fri, 17 Oct - Sun, 19 Oct

Air Canada flights from Toronto Island Airport to Chicago

Our best Air Canada deals on Toronto Island Airport to Chicago flight tickets
Air Canada
18 Oct
YTZ3:25 p.m.Toronto Island
5h 52m
1 stop
ORD8:17 p.m.Chicago O'Hare Intl
25 Oct
ORD8:40 a.m.Chicago O'Hare Intl
5h 05m
1 stop
YTZ2:45 p.m.Toronto Island
C$ 347
Find similar
Air Canada
4 Oct
YTZ3:25 p.m.Toronto Island
5h 41m
1 stop
ORD8:06 p.m.Chicago O'Hare Intl
6 Oct
ORD8:40 a.m.Chicago O'Hare Intl
7h 05m
1 stop
YTZ4:45 p.m.Toronto Island
C$ 366
Find similar
Air Canada
18 Oct
YTZ3:25 p.m.Toronto Island
5h 52m
1 stop
ORD8:17 p.m.Chicago O'Hare Intl
23 Oct
ORD8:40 a.m.Chicago O'Hare Intl
7h 05m
1 stop
YTZ4:45 p.m.Toronto Island
C$ 385
Find similar

Air Transat flights from Toronto Island Airport to Chicago

Our best Air Transat deals on Toronto Island Airport to Chicago flight tickets
Air Transat
5 Oct
YTZ7:50 a.m.Toronto Island
1h 49m
MDW8:39 a.m.Chicago Midway
7 Oct
MDW5:20 p.m.Chicago Midway
1h 42m
YTZ8:02 p.m.Toronto Island
C$ 388
Find similar
Air Transat
17 Oct
YTZ7:50 a.m.Toronto Island
1h 49m
MDW8:39 a.m.Chicago Midway
19 Oct
MDW9:35 a.m.Chicago Midway
1h 42m
YTZ12:17 p.m.Toronto Island
C$ 399
Find similar
Air Transat
16 Oct
YTZ7:50 a.m.Toronto Island
1h 49m
MDW8:39 a.m.Chicago Midway
20 Oct
MDW9:35 a.m.Chicago Midway
1h 42m
YTZ12:17 p.m.Toronto Island
C$ 410
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Toronto Island Airport to Chicago 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 96,600 searches. Data last updated 16 September 2025.
Use the filters below to find and compare flights from Toronto Island Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 14/10

7:30 p.m.-11:25 p.m.

1 stop4h 55m

Chicago Midway

Wed 22/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 323

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 18/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sat 25/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 16/10

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Sun 19/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 333

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 18/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Mon 20/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 336

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 6/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sun 9/11

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 337

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 14/10

7:30 p.m.-11:25 p.m.

1 stop4h 55m

Chicago Midway

Sun 19/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 340

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 18/10

3:25 p.m.-8:17 p.m.

1 stop5h 52m

Chicago O'Hare Intl

Sat 25/10

8:40 a.m.-2:45 p.m.

1 stop5h 05m

C$ 347

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 4/10

3:25 p.m.-8:06 p.m.

1 stop5h 41m

Chicago O'Hare Intl

Mon 6/10

8:40 a.m.-4:45 p.m.

1 stop7h 05m

C$ 366

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 5/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Tue 7/10

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 388

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 17/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sun 19/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 399

Flights are sorted by cheapest round-trip flights first.

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

See travel insights to Chicago from

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

The month of August is another great option to travel to Chicago, with average flight prices from Toronto Island Airport averaging around C$ 232.

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 C$ 655. 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 Tuesday because tickets tend to average around C$ 1,170. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the evening is the cheapest time of day to fly from Toronto Island Airport to Chicago when you can find flight prices for as low as C$ 622. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,163 per ticket.

What is the cheapest Toronto Island to Chicago flight route?

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

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

There is only 1 cabin class available to choose from on Toronto Island 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 Island Airport to Chicago flights?

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

When to book flights from Toronto Island Airport to Chicago

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

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

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

Best price found

C$ 211

Fastest flight time

1h 49m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Toronto Island Airport in the past 72 hours is C$ 211. The best round-trip flight deal from Toronto Island Airport to Chicago found on momondo in the last 72 hours is C$ 241.
The fastest flight from Toronto Island Airport to Chicago takes 1h 49m
Direct flights go from Toronto Island Airport to Chicago every day.
There is 1 airport near Chicago: Chicago Midway (MDW)
Search flight deals

  • How far is Toronto Island to Chicago by plane?

    The straight-line distance from Toronto Island to Chicago is 698.8 km. A reasonable flight in good conditions will take 1h 49m.

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

    Prices for flights from Toronto Island Airport to Chicago were last updated today.

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

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

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

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

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

Best airlines flying from Toronto Island Airport to Chicago

Compare and see reviews for airlines that fly from Toronto Island Airport to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 204Free CancellationRating
7.9
363 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 306Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights

  • Porter Airlines Flights From Toronto Island Airport to Chicago

    The lowest priced Porter Airlines flight from Toronto Island Airport to Chicago from the last 72 hours was C$ 148. Generally, Porter Airlines has 11 flights on this route every week with an average price of C$ 227. Porter Airlines is rated 7.9/10 by our users.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

Why use momondo?

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

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 Chicago from Toronto.

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

Flights from Toronto to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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?

Price alerts on flights to Chicago from Toronto 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 Chicago 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
Thu 16/10
Thu 23/10
By creating a price alert you accept our terms of use and privacy policy.

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 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport