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Cheap flights from Toronto Island Airport to Chicago from C$ 134

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 5/9. 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 Toronto Island Airport to Chicago

Cheap round-trip flights

Porter Airlines Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 206Porter Airlines
Find Deal
Tue, 16 Sep - Mon, 22 Sep
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$ 207Porter Airlines
Find Deal
Thu, 4 Sep - Sun, 7 Sep
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$ 208Porter Airlines
Find Deal
Thu, 4 Sep - Sun, 7 Sep
Porter Airlines Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 211Porter Airlines
Find Deal
Fri, 17 Oct - Sun, 19 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$ 212Porter Airlines
Find Deal
Thu, 4 Sep - Sun, 7 Sep
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$ 214Porter Airlines
Find Deal
Thu, 4 Sep - Sun, 7 Sep
Air Transat Logo
9:00 a.m. - 9:50 a.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 229Air Transat
Find Deal
Mon, 1 Sep - Wed, 3 Sep
Air Transat Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
Air Transat Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 258Air Transat
Find Deal
Tue, 7 Oct - Wed, 22 Oct
Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 270
Find Deal
Thu, 25 Sep - Mon, 29 Sep
Air Transat Logo
7:55 a.m. - 8:45 a.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
10:40 a.m. - 1:20 p.m.MDW-YTZ
1h 40mdirect
C$ 283Air Transat
Find Deal
Sun, 24 Aug - Sun, 31 Aug

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
16 Sep
YTZ3:35 p.m.Toronto Island
1h 49m
MDW4:24 p.m.Chicago Midway
22 Sep
MDW5:20 p.m.Chicago Midway
1h 42m
YTZ8:02 p.m.Toronto Island
C$ 206
Find similar
Porter Airlines
4 Sep
YTZ7:50 a.m.Toronto Island
1h 49m
MDW8:39 a.m.Chicago Midway
7 Sep
MDW9:35 a.m.Chicago Midway
1h 42m
YTZ12:17 p.m.Toronto Island
C$ 207
Find similar
Porter Airlines
4 Sep
YTZ7:50 a.m.Toronto Island
1h 49m
MDW8:39 a.m.Chicago Midway
7 Sep
MDW9:35 a.m.Chicago Midway
1h 42m
YTZ12:17 p.m.Toronto Island
C$ 208
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
1 Sep
YTZ9:00 a.m.Toronto Island
1h 50m
MDW9:50 a.m.Chicago Midway
3 Sep
MDW9:35 a.m.Chicago Midway
1h 42m
YTZ12:17 p.m.Toronto Island
C$ 229
Find similar
Air Transat
7 Oct
YTZ3:35 p.m.Toronto Island
1h 49m
MDW4:24 p.m.Chicago Midway
22 Oct
MDW5:20 p.m.Chicago Midway
1h 42m
YTZ8:02 p.m.Toronto Island
C$ 258
Find similar
Air Transat
24 Aug
YTZ7:55 a.m.Toronto Island
1h 50m
MDW8:45 a.m.Chicago Midway
31 Aug
MDW10:40 a.m.Chicago Midway
1h 40m
YTZ1:20 p.m.Toronto Island
C$ 283
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 31 July 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

Tue 16/9

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

Nonstop1h 49m

Chicago Midway

Mon 22/9

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

Nonstop1h 42m

C$ 206

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/9

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

Nonstop1h 49m

Chicago Midway

Sun 7/9

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

Nonstop1h 42m

C$ 207

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/9

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

Nonstop1h 49m

Chicago Midway

Sun 7/9

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

Nonstop1h 42m

C$ 208

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 17/10

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

Nonstop1h 49m

Chicago Midway

Sun 19/10

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

Nonstop1h 42m

C$ 211

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/9

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

Nonstop1h 49m

Chicago Midway

Sun 7/9

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

Nonstop1h 42m

C$ 212

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/9

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

Nonstop1h 49m

Chicago Midway

Sun 7/9

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

Nonstop1h 42m

C$ 214

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 1/9

9:00 a.m.-9:50 a.m.

Nonstop1h 50m

Chicago Midway

Wed 3/9

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

Nonstop1h 42m

C$ 229

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 7/10

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

Nonstop1h 49m

Chicago Midway

Wed 22/10

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

Nonstop1h 42m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 25/9

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

Nonstop1h 49m

Chicago Midway

Mon 29/9

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

Nonstop1h 42m

C$ 270

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 24/8

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Sun 31/8

10:40 a.m.-1:20 p.m.

Nonstop1h 40m

C$ 283

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 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, March 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$ 262. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Toronto Island Airport during the month June is also very affordable. Most momondo users find prices during this month for around C$ 270.

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 Tuesday when prices can be found for as low as C$ 323. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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$ 345.

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$ 324. In contrast, the most expensive time of day to depart to Chicago Midway Airport is at noon when prices are around C$ 572.

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 are 1 cabin classes 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$ 134

Fastest flight time

1h 49m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Toronto Island Airport in the past 72 hours is C$ 134. The best round-trip flight deal from Toronto Island Airport to Chicago Midway Airport found on momondo in the last 72 hours is C$ 206.
The fastest flight from Toronto Island Airport to Chicago Midway Airport takes 1h 49m
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 49m.

  • 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$ 229Free CancellationRating
8.0
318 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 13 times per week, with 318 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$ 166 (round-trip), much lower than the average airfare cost of C$ 235 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
Hammond
Munster
Benton Harbor
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.

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