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Cheap flights from Toronto Island Airport to Chicago from C$ 170

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 1/8. 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

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
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 277Porter Airlines
Thu, 11 Jun - Sun, 14 Jun
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 279Porter Airlines
Mon, 18 May - Wed, 20 May
Air Transat Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Air Transat Logo
10:15 a.m. - 12:55 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 280Air Transat
Fri, 29 May - Fri, 5 Jun
Porter Airlines Logo
8:45 a.m. - 9:35 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 281Porter Airlines
Mon, 15 Jun - Mon, 22 Jun
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 283Porter Airlines
Wed, 1 Jul - Thu, 9 Jul
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 284Porter Airlines
Thu, 25 Jun - Sun, 28 Jun
Porter Airlines Logo
8:50 a.m. - 9:40 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 285Porter Airlines
Tue, 30 Jun - Sat, 18 Jul
Air Transat Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Air Transat Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 287Air Transat
Fri, 22 May - Sun, 24 May
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 288Porter Airlines
Fri, 22 May - Tue, 26 May
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:15 a.m. - 12:55 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 289Porter Airlines
Thu, 4 Jun - Sun, 7 Jun

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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
24 May
YTZ8:55 a.m.Toronto Island
1h 50m
MDW9:45 a.m.Chicago Midway
27 May
MDW3:20 p.m.Chicago Midway
1h 40m
YTZ6:00 p.m.Toronto Island
C$ 279
Porter Airlines
21 May
YTZ8:55 a.m.Toronto Island
1h 50m
MDW9:45 a.m.Chicago Midway
2 Jun
MDW10:15 a.m.Chicago Midway
1h 40m
YTZ12:55 p.m.Toronto Island
C$ 280
Porter Airlines
15 Jun
YTZ8:45 a.m.Toronto Island
1h 50m
MDW9:35 a.m.Chicago Midway
22 Jun
MDW3:20 p.m.Chicago Midway
1h 40m
YTZ6:00 p.m.Toronto Island
C$ 281

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
22 May
YTZ1:45 p.m.Toronto Island
1h 50m
MDW2:35 p.m.Chicago Midway
24 May
MDW3:20 p.m.Chicago Midway
1h 40m
YTZ6:00 p.m.Toronto Island
C$ 287
Air Transat
24 May
YTZ8:55 a.m.Toronto Island
1h 50m
MDW9:45 a.m.Chicago Midway
30 May
MDW10:30 a.m.Chicago Midway
1h 40m
YTZ1:10 p.m.Toronto Island
C$ 306
Air Transat
24 May
YTZ8:55 a.m.Toronto Island
1h 50m
MDW9:45 a.m.Chicago Midway
29 May
MDW3:20 p.m.Chicago Midway
1h 40m
YTZ6:00 p.m.Toronto Island
C$ 332

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 4 May 2026.
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

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/6

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Sun 14/6

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 277

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 18/5

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 20/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 279

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 29/5

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Fri 5/6

10:15 a.m.-12:55 p.m.

Nonstop1h 40m

C$ 280

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 15/6

8:45 a.m.-9:35 a.m.

Nonstop1h 50m

Chicago Midway

Mon 22/6

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 281

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 1/7

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Thu 9/7

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 283

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 25/6

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Sun 28/6

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 284

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 30/6

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Sat 18/7

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 285

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 22/5

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Sun 24/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 287

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 22/5

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Tue 26/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 288

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/6

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Sun 7/6

10:15 a.m.-12:55 p.m.

Nonstop1h 40m

C$ 289

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 typical price of a round-trip flight between Toronto Island Airport and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

In general, February 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$ 0. If you are unable to visit Chicago Midway Airport during the month of February, 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$ 247.

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 Monday when prices can be found for as low as C$ 253. 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$ 317.

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 afternoon. Flights from Toronto Island Airport to Chicago Midway Airport during this time can be as low as C$ 286. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 658.

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

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$ 150

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$ 150. The best round-trip flight deal from Toronto Island Airport to Chicago Midway Airport found on momondo in the last 72 hours is C$ 272.
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

Frequently asked questions about flying from Toronto Island Airport to Chicago Midway Airport

  • 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$ 192Free CancellationRating
8.0
436 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 436 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$ 192 (round-trip), much lower than the average airfare cost of C$ 284 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
Merrillville
Hammond
Munster

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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