$130+ Cheap flights from Toronto (YTO) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
Oct 19 — Oct 261
Round-trip
1 adult, Economy
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Find cheap flights from Toronto to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Toronto to Midway
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Cheapest flights from Toronto to MidwayExplore the most affordable flight options available from Toronto to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 19, 2026.
Explore the most affordable flight options available from Toronto to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:10 am -
Nonstop1h 50m
Tue 10/133:20 pm -
Nonstop1h 40m
Deal found 9/19![Porter Airlines logo]()
$206
This Trip.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:45 pm -
Nonstop1h 50m
Sun 10/411:45 am -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$207
This Trip.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:45 pm -
Nonstop1h 50m
Sun 10/1111:45 am -
Nonstop1h 40m
Deal found 9/16![Porter Airlines logo]()
$210
This Justfly.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/51:45 pm -
Nonstop1h 50m
Wed 10/711:45 am -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$211
This Porter Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:45 pm -
Nonstop1h 50m
Sat 10/311:45 am -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$212
This Expedia deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1110:10 am -
Nonstop1h 50m
Sun 10/183:20 pm -
Nonstop1h 40m
Deal found 9/16![Porter Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:10 am -
Nonstop1h 50m
Fri 10/23:20 pm -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$215
This Trip.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:10 am -
Nonstop1h 50m
Fri 10/93:20 pm -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$219
This SmartFares deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:45 pm -
Nonstop1h 50m
Tue 10/133:20 pm -
Nonstop1h 40m
Deal found 9/19![Air Transat logo]()
$227
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:08 pm -
1 stop7h 25m
Sat 10/36:40 pm -
1 stop3h 19m
Deal found 9/18![Delta logo]()
$228
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:00 am -
1 stop4h 32m
Sat 10/101:27 pm -
1 stop8h 29m
Deal found 9/15![Delta logo]()
$230
This Trip.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:10 am -
Nonstop1h 50m
Sun 10/411:45 am -
Nonstop1h 40m
Deal found 9/18![Multiple Airlines logo]()
$233
Best flights from Toronto to MidwayDiscover carefully curated flight deals from Toronto to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 19, 2026.
Discover carefully curated flight deals from Toronto to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 19, 2026.
This Porter Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:45 pm -
Nonstop1h 50m
Sat 10/311:45 am -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:08 pm -
1 stop7h 25m
Sat 10/36:40 pm -
1 stop3h 19m
Deal found 9/18![Delta logo]()
$228
This Trip.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:10 am -
Nonstop1h 50m
Sun 10/411:45 am -
Nonstop1h 40m
Deal found 9/18![Multiple Airlines logo]()
$240
This Trip.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2910:10 am -
Nonstop1h 50m
Sat 10/1011:45 am -
Nonstop1h 40m
Deal found 9/14![Air Transat logo]()
$312
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1012:10 pm -
1 stop6h 50m
Tue 10/209:29 am -
1 stop6h 50m
Deal found 9/18![Delta logo]()
$236
This Porter Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/410:10 am -
Nonstop1h 50m
Fri 10/93:20 pm -
Nonstop1h 40m
Deal found 9/17![Porter Airlines logo]()
$241
This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:45 pm -
Nonstop1h 50m
Sun 10/411:45 am -
Nonstop1h 40m
Deal found 9/16![Multiple Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:45 am -
1 stop4h 06m
Tue 11/249:30 am -
1 stop3h 00m
Deal found 9/18![Delta logo]()
$236
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1012:10 pm -
1 stop6h 50m
Fri 10/166:44 pm -
1 stop3h 12m
Deal found 9/17![Delta logo]()
$236
This Trip.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:45 pm -
Nonstop1h 50m
Sun 10/1111:45 am -
Nonstop1h 40m
Deal found 9/15![Porter Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:45 am -
1 stop4h 06m
Thu 11/191:31 pm -
1 stop8h 26m
Deal found 9/18![Delta logo]()
$236
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/61:45 pm -
Nonstop1h 50m
Wed 10/73:20 pm -
Nonstop1h 40m
Deal found 9/14![Porter Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:00 am -
1 stop7h 51m
Sun 11/229:30 am -
1 stop6h 50m
Deal found 9/17![Delta logo]()
$237
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/610:10 am -
Nonstop1h 50m
Thu 10/811:45 am -
Nonstop1h 40m
Deal found 9/14![Porter Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:05 pm -
1 stop3h 17m
Tue 10/69:29 am -
1 stop6h 50m
Deal found 9/17![Delta logo]()
$237
This KAYAK deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1210:10 am -
Nonstop1h 50m
Thu 10/153:20 pm -
Nonstop1h 40m
Deal found 9/15![Porter Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:00 am -
1 stop7h 47m
Wed 10/141:27 pm -
1 stop8h 29m
Deal found 9/14![Delta logo]()
$238
This Justfly.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/810:10 am -
Nonstop1h 50m
Sat 10/1711:45 am -
Nonstop1h 40m
Deal found 9/14![Porter Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:00 am -
1 stop4h 07m
Sat 10/36:40 pm -
1 stop3h 19m
Deal found 9/14![Delta logo]()
$238
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
1 stop4h 32m
Sat 10/246:44 pm -
1 stop3h 12m
Deal found 9/15![Delta logo]()
$238
This oojo deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:10 am -
Nonstop1h 50m
Fri 10/93:20 pm -
Nonstop1h 40m
Deal found 9/16![Porter Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am -
1 stop7h 47m
Sat 10/246:44 pm -
1 stop3h 12m
Deal found 9/15![Delta logo]()
$238
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:00 am -
1 stop4h 32m
Mon 10/129:29 am -
1 stop6h 50m
Deal found 9/14![Delta logo]()
$269
Last-minute flights from Toronto to MidwayDiscover last-minute flight deals from Toronto to Midway. Data last updated September 19, 2026 and is based on user searches.
Discover last-minute flight deals from Toronto to Midway. Data last updated September 19, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:45 pm -
Nonstop1h 50m
Sun 10/411:45 am -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$207
This Porter Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:45 pm -
Nonstop1h 50m
Sat 10/311:45 am -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:10 am -
Nonstop1h 50m
Fri 10/23:20 pm -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$215
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:08 pm -
1 stop7h 25m
Sat 10/36:40 pm -
1 stop3h 19m
Deal found 9/18![Delta logo]()
$228
This Trip.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:10 am -
Nonstop1h 50m
Sun 10/411:45 am -
Nonstop1h 40m
Deal found 9/18![Multiple Airlines logo]()
$233
This Justfly.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/51:45 pm -
Nonstop1h 50m
Wed 10/711:45 am -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:10 am -
Nonstop1h 50m
Tue 10/133:20 pm -
Nonstop1h 40m
Deal found 9/19![Porter Airlines logo]()
$206
This Trip.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:45 pm -
Nonstop1h 50m
Sun 10/1111:45 am -
Nonstop1h 40m
Deal found 9/16![Porter Airlines logo]()
$210
This Trip.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:10 am -
Nonstop1h 50m
Fri 10/93:20 pm -
Nonstop1h 40m
Deal found 9/18![Porter Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/712:10 pm -
1 stop6h 50m
Sun 10/119:29 am -
1 stop6h 50m
Deal found 9/15![Delta logo]()
$230
This SmartFares deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:45 pm -
Nonstop1h 50m
Tue 10/133:20 pm -
Nonstop1h 40m
Deal found 9/19![Air Transat logo]()
$227
This Expedia deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1110:10 am -
Nonstop1h 50m
Sun 10/183:20 pm -
Nonstop1h 40m
Deal found 9/16![Porter Airlines logo]()
$214
One-way flights from Toronto to MidwaySearch for one-way flight options from Toronto to Midway. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
Search for one-way flight options from Toronto to Midway. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3010:10 am -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Porter Airlines logo]()
$130
This FlightHub deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1610:10 am -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Porter Airlines logo]()
$131
This Trip.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Porter Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Porter Airlines logo]()
$133
This FlightHub deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/121:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Porter Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Porter Airlines logo]()
$135
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:08 pm -
1 stop7h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$144
This Mytrip deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Air Transat logo]()
$146
This Porter Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:10 am -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Porter Airlines logo]()
$151
This Porter Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/31:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Porter Airlines logo]()
$152
This FlightHub deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:45 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Air Transat logo]()
$153
This Kissandfly.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:00 am -
1 stop7h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![KLM logo]()
$158
Find flight deals from Toronto to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Toronto (YTO) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $206 (Kiwi.com) |
One-way from | $130 (Mytrip) |
Popular in | June |
Cheapest in | September |
Average price | $190 |
Good round-trip deal | $230 or less |
Good one-way deal | $179 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Toronto to Midway 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, Cheapflights users made 7,457,451 searches. Data last updated September 19, 2026.
Use the filters below to find and compare flights from Toronto to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Thu 10/15
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Mon 10/5
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Tue 9/29
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$131
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Thu 10/22
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Sun 10/18
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Fri 10/2
12:08 pm-6:33 pm
1 stop7h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$144
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Sat 10/3
6:00 am-9:07 am
1 stop4h 07m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$144
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Thu 10/1
6:00 am-9:07 am
1 stop4h 07m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Thu 10/15
12:10 pm-6:00 pm
1 stop6h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Sat 10/17
6:00 am-9:32 am
1 stop4h 32m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
Showing 1-10 of 46 resultsSorted by cheapest first
Compare providers for flights from Toronto to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Toronto to Midway in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Toronto-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toronto-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toronto-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Toronto-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Toronto-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Toronto to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Toronto with our price prediction graph.
YTO-MDW
YTZ-MDW
YYZ-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Toronto to Chicago Midway Airport
YTO-MDW
YTZ-MDW
YYZ-MDW
What is the cheapest month to book a flight from Toronto to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from Toronto to Chicago Midway Airport (average of $204). Flying from Toronto to Chicago Midway Airport in June is currently the most expensive (average of $429). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from YTO to MDW?
Find hourly flight availability from Toronto to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 19, 2026.
It’s optimal to fly from Toronto to Chicago Midway Airport in the morning. By choosing this option you can save up to 38% on the cost of your flight, compared to a flight in the afternoon.
Weekly flight availability from Toronto to Chicago Midway Airport
Explore weekly flight availability from Toronto to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 19, 2026.
The most flights from YTO to MDW are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Toronto to Chicago Midway Airport?
Airfare is below average for this route at the moment.
Toronto to Chicago Midway Airport flights typically cost between $272 and $412 in October.The cheapest round-trip price found within the last 5 days was $206 on Porter Airlines (Oct 7-Oct 13).
How often are flights from Toronto to Chicago delayed?
About 16% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 107 minutes.
What is the most punctual flight time for Toronto to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Toronto to Chicago flights?
Over the last year, Porter Airlines have had the lowest number of delays on this route, with just 15% of flights being delayed.
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated September 19, 2026.
Peruse reviews from past customers who have flown with Porter Airlines from Toronto to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.6
Entertainment
6.9
Overall
8.0
Boarding
8.2
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Crew
8.6
Food
7.6
Entertainment
6.9
Overall
8.0
Boarding
8.2
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentD,Sep 2026
YHM - YVR
Related info for your journey
Find useful and relevant information for your journey from Toronto to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Top airline flying from Toronto to Midway
Discover the top airline that operate flights from Toronto to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$185 | Average$365 | FlexibilityNo cancel fee | On-time52% |