Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Toronto Island Airport to Chicago from C$ 182

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 15/12. 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

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

Enter your travel dates to find the best prices.
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$ 259Porter Airlines
Find Deal
Sun, 23 Nov - Fri, 12 Dec
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$ 262Porter Airlines
Find Deal
Mon, 24 Nov - Mon, 8 Dec
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$ 263Porter Airlines
Find Deal
Tue, 18 Nov - Thu, 20 Nov
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$ 270Porter Airlines
Find Deal
Wed, 19 Nov - Fri, 21 Nov
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 272Porter Airlines
Find Deal
Fri, 14 Nov - Mon, 17 Nov
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$ 273Porter Airlines
Find Deal
Mon, 17 Nov - Thu, 20 Nov
Air Transat Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 283Air Transat
Find Deal
Mon, 17 Nov - Wed, 19 Nov
Air Transat Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 290Air Transat
Find Deal
Thu, 20 Nov - Sun, 23 Nov
Multiple Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Multiple Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 308Multiple Airlines
Find Deal
Fri, 14 Nov - Mon, 17 Nov
Air Transat Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 310Air Transat
Find Deal
Fri, 14 Nov - Sun, 16 Nov

Porter Airlines flights from Toronto Island Airport to Chicago Midway Airport

Our best Porter Airlines deals on Toronto Island Airport to Chicago Midway Airport flight tickets
Porter Airlines
23 Nov
YTZ9:15 a.m.Toronto Island
1h 50m
MDW10:05 a.m.Chicago Midway
12 Dec
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
C$ 259
Find similar
Porter Airlines
24 Nov
YTZ9:15 a.m.Toronto Island
1h 50m
MDW10:05 a.m.Chicago Midway
8 Dec
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
C$ 262
Find similar
Porter Airlines
18 Nov
YTZ9:15 a.m.Toronto Island
1h 50m
MDW10:05 a.m.Chicago Midway
20 Nov
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
C$ 263
Find similar

Air Transat flights from Toronto Island Airport to Chicago Midway Airport

Our best Air Transat deals on Toronto Island Airport to Chicago Midway Airport flight tickets
Air Transat
17 Nov
YTZ2:30 p.m.Toronto Island
1h 50m
MDW3:20 p.m.Chicago Midway
19 Nov
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
C$ 283
Find similar
Air Transat
20 Nov
YTZ2:30 p.m.Toronto Island
1h 50m
MDW3:20 p.m.Chicago Midway
23 Nov
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
C$ 290
Find similar
Air Transat
14 Nov
YTZ9:15 a.m.Toronto Island
1h 50m
MDW10:05 a.m.Chicago Midway
16 Nov
MDW11:00 a.m.Chicago Midway
1h 42m
YTZ1:42 p.m.Toronto Island
C$ 310
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Toronto Island Airport to Chicago Midway 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 96,600 searches. Data last updated 1 November 2025.
Use the filters below to find and compare flights from Toronto Island Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 23/11

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

Nonstop1h 50m

Chicago Midway

Fri 12/12

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

Nonstop1h 42m

C$ 259

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 24/11

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

Nonstop1h 50m

Chicago Midway

Mon 8/12

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

Nonstop1h 42m

C$ 262

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 18/11

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

Nonstop1h 50m

Chicago Midway

Thu 20/11

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

Nonstop1h 42m

C$ 263

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 19/11

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

Nonstop1h 50m

Chicago Midway

Fri 21/11

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

Nonstop1h 42m

C$ 270

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 14/11

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Mon 17/11

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 272

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 17/11

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

Nonstop1h 50m

Chicago Midway

Thu 20/11

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

Nonstop1h 42m

C$ 273

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 17/11

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Wed 19/11

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

Nonstop1h 42m

C$ 283

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 20/11

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Sun 23/11

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

Nonstop1h 42m

C$ 290

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 14/11

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Mon 17/11

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 308

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 14/11

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

Nonstop1h 50m

Chicago Midway

Sun 16/11

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

Nonstop1h 42m

C$ 310

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 Midway 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 Chicago Midway Airport?

In general, July is the cheapest month to fly from Toronto Island Airport to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 255. If you are unable to visit Chicago Midway Airport during the month of July, then departing from Toronto Island Airport during the month September is also very affordable. Most momondo users find prices during this month for around C$ 255.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

The cheapest day to depart on your flight to Chicago Midway Airport is on a Friday when prices can be found for as low as C$ 304. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Toronto Island Airport because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 330.

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

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is in the morning. Flights from Toronto Island Airport to Chicago Midway Airport during this time can be as low as C$ 313. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 679.

What is the cheapest Toronto Island to Chicago Midway flight route?

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

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

There is only 1 cabin class available to choose from on Toronto Island to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from Toronto Island Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto Island Airport to Chicago Midway Airport 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 Midway Airport (YTZ to MDW) flight deals and tips

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

Best price found

C$ 197

Fastest flight time

1h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Toronto Island Airport in the past 72 hours is C$ 197. The best round-trip flight deal from Toronto Island Airport to Chicago Midway Airport found on momondo in the last 72 hours is C$ 348.
The fastest flight from Toronto Island Airport to Chicago Midway Airport takes 1h 50m
Direct flights go from Toronto Island Airport to Chicago Midway Airport every day.
Search flight deals

  • How far is Toronto Island to Chicago Midway by plane?

    Chicago Midway is 711.3 km away from Toronto Island. In terms of flight time, this usually takes a little over 1h 50m.

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

    Prices for flights from Toronto Island Airport to Chicago Midway Airport are updated daily.

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

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

    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 Midway Airport.

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

    The travel and health documents you'll need for your trip to Chicago Midway Airport 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 Midway Airport. 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 Midway Airport?

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

Best airlines flying from Toronto Island Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from Toronto Island Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 198Free CancellationRating
8.0
384 reviews
Search Porter Airlines flights

  • Porter Airlines Flights From Toronto Island Airport to Chicago Midway Airport

    Porter Airlines flies from Toronto Island Airport to Chicago Midway Airport around 1 time per week, with 384 momondo users rating the airline 8.0/10. The cheapest Porter Airlines deal from Toronto Island Airport to Chicago Midway Airport in the last 72 hours was C$ 198 (round-trip), much lower than the average airfare cost of C$ 291 for Porter Airlines flights on this route.

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?

Finding the right flight to Chicago from Toronto is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Toronto to Chicago flights to just show those with flexible booking policies.

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?

Yes momondo offers price alerts on flights to Chicago from Toronto. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago Midway 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
Mon 1/12
Mon 8/12
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago