$133+ Cheap flights from Toronto (YTO) to Midway (MDW)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — MDW
Sep 6 — Sep 131
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 August 7, 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 August 7, 2026.
This FlightHub deal was found by Cheapflights users on 8/5. 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.
Tue 9/11:45 pm -
Nonstop1h 50m
Sun 9/2011:45 am -
Nonstop1h 40m
Deal found 8/5![Porter Airlines logo]()
$200
This FlightHub deal was found by Cheapflights users on 8/6. 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 9/111:45 pm -
Nonstop1h 50m
Sat 9/1211:45 am -
Nonstop1h 40m
Deal found 8/6![Porter Airlines logo]()
$201
This Justfly.com deal was found by Cheapflights users on 8/4. 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.
Fri 9/111:45 pm -
Nonstop1h 50m
Tue 9/1511:45 am -
Nonstop1h 40m
Deal found 8/4![Porter Airlines logo]()
$202
This Cheapflightsfares deal was found by Cheapflights users on 8/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:45 pm -
Nonstop1h 50m
Tue 9/811:45 am -
Nonstop1h 40m
Deal found 8/7![Porter Airlines logo]()
$204
This Trip.com deal was found by Cheapflights users on 8/4. 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.
Mon 8/311:45 pm -
Nonstop1h 50m
Tue 9/13:20 pm -
Nonstop1h 40m
Deal found 8/4![Porter Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
Tue 9/810:10 am -
Nonstop1h 50m
Wed 9/233:20 pm -
Nonstop1h 40m
Deal found 8/6![Porter Airlines logo]()
$207
This Trip.com deal was found by Cheapflights users on 8/4. 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.
Sat 8/298:50 am -
Nonstop1h 50m
Wed 9/211:45 am -
Nonstop1h 40m
Deal found 8/4![Porter Airlines logo]()
$208
This Trip.com deal was found by Cheapflights users on 8/4. 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 8/261:45 pm -
Nonstop1h 50m
Wed 9/211:45 am -
Nonstop1h 40m
Deal found 8/4![Porter Airlines logo]()
$209
This oojo deal was found by Cheapflights users on 8/3. 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.
Thu 8/278:55 am -
Nonstop1h 50m
Tue 9/13:20 pm -
Nonstop1h 40m
Deal found 8/3![Porter Airlines logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 8/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/298:50 am -
Nonstop1h 50m
Tue 9/111:45 am -
Nonstop1h 40m
Deal found 8/4![Porter Airlines logo]()
$212
This Cheapflightsfares deal was found by Cheapflights users on 8/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:55 am -
Nonstop1h 50m
Mon 8/2410:25 am -
Nonstop1h 40m
Deal found 8/2![Porter Airlines logo]()
$213
This Justfly.com deal was found by Cheapflights users on 8/6. 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 8/278:55 am -
Nonstop1h 50m
Wed 9/211:45 am -
Nonstop1h 40m
Deal found 8/6![Porter Airlines logo]()
$215
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 August 7, 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 August 7, 2026.
This FlightHub deal was found by Cheapflights users on 8/4. 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.
Wed 9/2310:10 am -
Nonstop1h 50m
Sun 9/273:20 pm -
Nonstop1h 40m
Deal found 8/4![Porter Airlines logo]()
$202
This Delta deal was found by Cheapflights users on 8/2. 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 10/316:00 am -
1 stop4h 17m
Tue 11/109:30 am -
1 stop3h 03m
Deal found 8/2![Delta logo]()
$235
This Trip.com deal was found by Cheapflights users on 8/3. 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.
Sat 8/228:50 am -
Nonstop1h 50m
Thu 8/2710:25 am -
Nonstop1h 40m
Deal found 8/3![Porter Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 8/2. 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 8/2712:09 pm -
1 stop7h 24m
Sun 8/301:25 pm -
1 stop8h 38m
Deal found 8/2![Delta logo]()
$235
This Porter Airlines deal was found by Cheapflights users on 8/3. 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 9/91:45 pm -
Nonstop1h 50m
Thu 9/1011:45 am -
Nonstop1h 40m
Deal found 8/3![Porter Airlines logo]()
$220
This Delta deal was found by Cheapflights users on 8/2. 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 10/249:40 am -
1 stop4h 07m
Fri 10/309:29 am -
1 stop6h 50m
Deal found 8/2![Delta logo]()
$235
This Porter Airlines deal was found by Cheapflights users on 8/2. 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.
Thu 9/1010:10 am -
Nonstop1h 50m
Sun 9/133:20 pm -
Nonstop1h 40m
Deal found 8/2![Porter Airlines logo]()
$221
This Delta deal was found by Cheapflights users on 8/2. 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 9/1612:08 pm -
1 stop7h 25m
Wed 9/239:29 am -
1 stop6h 51m
Deal found 8/2![Delta logo]()
$235
This Porter Airlines deal was found by Cheapflights users on 8/3. 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.
Thu 8/278:55 am -
Nonstop1h 50m
Sun 8/3010:20 am -
Nonstop1h 40m
Deal found 8/3![Porter Airlines logo]()
$228
This Delta deal was found by Cheapflights users on 8/2. 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 9/44:10 pm -
1 stop3h 23m
Sun 9/136:40 pm -
1 stop3h 19m
Deal found 8/2![Delta logo]()
$235
This Cheapflightsfares deal was found by Cheapflights users on 8/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:50 am -
Nonstop1h 50m
Tue 8/2510:25 am -
Nonstop1h 40m
Deal found 8/6![Porter Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 8/5. 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 8/266:10 am -
1 stop7h 29m
Thu 8/271:25 pm -
1 stop8h 38m
Deal found 8/5![Delta logo]()
$290
This Trip.com deal was found by Cheapflights users on 8/6. 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 9/11:45 pm -
Nonstop1h 50m
Thu 9/33:20 pm -
Nonstop1h 40m
Deal found 8/6![Porter Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 8/4. 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 8/256:10 am -
1 stop4h 07m
Sat 8/299:24 am -
1 stop4h 56m
Deal found 8/4![Delta logo]()
$290
This Trip.com deal was found by Cheapflights users on 8/3. 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.
Mon 8/178:55 am -
Nonstop1h 50m
Thu 8/2010:25 am -
Nonstop1h 40m
Deal found 8/3![Porter Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 8/6. 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 9/109:45 am -
1 stop8h 12m
Sun 9/136:40 pm -
1 stop3h 19m
Deal found 8/6![Delta logo]()
$293
This Cheapflightsfares deal was found by Cheapflights users on 8/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/211:45 pm -
Nonstop1h 50m
Mon 8/243:15 pm -
Nonstop1h 40m
Deal found 8/5![Porter Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 8/3. 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 9/116:00 am -
1 stop4h 07m
Mon 9/149:24 am -
1 stop6h 56m
Deal found 8/3![Delta logo]()
$302
This Delta deal was found by Cheapflights users on 8/3. 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 8/186:10 am -
1 stop7h 29m
Sat 8/221:25 pm -
1 stop8h 34m
Deal found 8/3![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 8/3. 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 8/196:10 am -
1 stop7h 29m
Sat 8/229:24 am -
1 stop7h 00m
Deal found 8/3![Delta logo]()
$309
Last-minute flights from Toronto to MidwayDiscover last-minute flight deals from Toronto to Midway. Data last updated August 7, 2026 and is based on user searches.
Discover last-minute flight deals from Toronto to Midway. Data last updated August 7, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 8/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:55 am -
Nonstop1h 50m
Mon 8/2410:25 am -
Nonstop1h 40m
Deal found 8/2![Porter Airlines logo]()
$213
This Trip.com deal was found by Cheapflights users on 8/4. 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 8/261:45 pm -
Nonstop1h 50m
Wed 9/211:45 am -
Nonstop1h 40m
Deal found 8/4![Porter Airlines logo]()
$209
This oojo deal was found by Cheapflights users on 8/3. 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.
Thu 8/278:55 am -
Nonstop1h 50m
Tue 9/13:20 pm -
Nonstop1h 40m
Deal found 8/3![Porter Airlines logo]()
$211
This Justfly.com deal was found by Cheapflights users on 8/6. 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 8/278:55 am -
Nonstop1h 50m
Wed 9/211:45 am -
Nonstop1h 40m
Deal found 8/6![Porter Airlines logo]()
$215
This Trip.com deal was found by Cheapflights users on 8/4. 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.
Sat 8/298:50 am -
Nonstop1h 50m
Wed 9/211:45 am -
Nonstop1h 40m
Deal found 8/4![Porter Airlines logo]()
$208
This Cheapflightsfares deal was found by Cheapflights users on 8/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/298:50 am -
Nonstop1h 50m
Tue 9/111:45 am -
Nonstop1h 40m
Deal found 8/4![Porter Airlines logo]()
$212
This Trip.com deal was found by Cheapflights users on 8/4. 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.
Mon 8/311:45 pm -
Nonstop1h 50m
Tue 9/13:20 pm -
Nonstop1h 40m
Deal found 8/4![Porter Airlines logo]()
$206
This FlightHub deal was found by Cheapflights users on 8/5. 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.
Tue 9/11:45 pm -
Nonstop1h 50m
Sun 9/2011:45 am -
Nonstop1h 40m
Deal found 8/5![Porter Airlines logo]()
$200
This Cheapflightsfares deal was found by Cheapflights users on 8/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:45 pm -
Nonstop1h 50m
Tue 9/811:45 am -
Nonstop1h 40m
Deal found 8/7![Porter Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
Tue 9/810:10 am -
Nonstop1h 50m
Wed 9/233:20 pm -
Nonstop1h 40m
Deal found 8/6![Porter Airlines logo]()
$207
This FlightHub deal was found by Cheapflights users on 8/6. 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 9/111:45 pm -
Nonstop1h 50m
Sat 9/1211:45 am -
Nonstop1h 40m
Deal found 8/6![Porter Airlines logo]()
$201
This Justfly.com deal was found by Cheapflights users on 8/4. 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.
Fri 9/111:45 pm -
Nonstop1h 50m
Tue 9/1511:45 am -
Nonstop1h 40m
Deal found 8/4![Porter Airlines logo]()
$202
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 August 7, 2026.
Search for one-way flight options from Toronto to Midway. Find affordable one-way fares based on user searches. Data last updated August 7, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 8/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/298:50 am -
Nonstop1h 50m
Deal found 8/6![Porter Airlines logo]()
$133
This Booking.com deal was found by Cheapflights users on 8/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:10 am -
Nonstop1h 50m
Deal found 8/4![Air Transat logo]()
$135
This Porter Airlines deal was found by Cheapflights users on 8/7. 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 9/111:45 pm -
Nonstop1h 50m
Deal found 8/7![Porter Airlines logo]()
$137
This Trip.com deal was found by Cheapflights users on 8/7. 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 8/271:45 pm -
Nonstop1h 50m
Deal found 8/7![Porter Airlines logo]()
$138
This Trip.com deal was found by Cheapflights users on 8/5. 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.
Mon 8/311:45 pm -
Nonstop1h 50m
Deal found 8/5![Porter Airlines logo]()
$141
This FlightHub deal was found by Cheapflights users on 8/4. 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.
Sun 8/308:50 am -
Nonstop1h 50m
Deal found 8/4![Porter Airlines logo]()
$142
This Delta deal was found by Cheapflights users on 8/2. 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 8/246:10 am -
1 stop7h 29m
Deal found 8/2![Delta logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Tue 8/188:55 am -
Nonstop1h 50m
Deal found 8/3![Porter Airlines logo]()
$144
This Justfly.com deal was found by Cheapflights users on 8/4. 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.
Wed 8/261:45 pm -
Nonstop1h 50m
Deal found 8/4![Porter Airlines logo]()
$147
This Delta deal was found by Cheapflights users on 8/2. 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 8/256:10 am -
1 stop4h 07m
Deal found 8/2![Delta logo]()
$147
This Delta deal was found by Cheapflights users on 8/7. 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 9/1212:08 pm -
1 stop5h 49m
Deal found 8/7![Delta logo]()
$151
This Kissandfly.com deal was found by Cheapflights users on 8/3. 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.
Wed 10/1412:10 pm -
1 stop6h 50m
Deal found 8/3![KLM logo]()
$152
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 August 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $200 (FlightHub) |
One-way from | $133 (Cheapflightsfares) |
Popular in | June |
Cheapest in | September |
Average price | $205 |
Good round-trip deal | $204 or less |
Good one-way deal | $137 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 2,558,603 searches. Data last updated August 7, 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
Wed 9/23
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Sun 9/27
3:20 pm-6:00 pm
Nonstop1h 40m
$202
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Sat 8/22
8:50 am-9:40 am
Nonstop1h 50m
Chicago Midway
Thu 8/27
10:25 am-1:05 pm
Nonstop1h 40m
$212
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Wed 9/9
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Thu 9/10
11:45 am-2:25 pm
Nonstop1h 40m
$220
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Thu 9/10
10:10 am-11:00 am
Nonstop1h 50m
Chicago Midway
Sun 9/13
3:20 pm-6:00 pm
Nonstop1h 40m
$221
TorontoChicago
YTZ Toronto Island - MDW Chicago Midway
YTZMDW
Toronto Island
Thu 8/27
8:55 am-9:45 am
Nonstop1h 50m
Chicago Midway
Sun 8/30
10:20 am-1:00 pm
Nonstop1h 40m
$228
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Sat 10/31
6:00 am-9:17 am
1 stop4h 17m
Chicago Midway
Tue 11/10
9:30 am-1:33 pm
1 stop3h 03m
$235
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Thu 8/27
12:09 pm-6:33 pm
1 stop7h 24m
Chicago Midway
Sun 8/30
1:25 pm-11:03 pm
1 stop8h 38m
$235
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Sat 10/24
9:40 am-12:47 pm
1 stop4h 07m
Chicago Midway
Fri 10/30
9:29 am-5:19 pm
1 stop6h 50m
$235
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Wed 9/16
12:08 pm-6:33 pm
1 stop7h 25m
Chicago Midway
Wed 9/23
9:29 am-5:20 pm
1 stop6h 51m
$235
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Fri 9/4
4:10 pm-6:33 pm
1 stop3h 23m
Chicago Midway
Sun 9/13
6:40 pm-10:59 pm
1 stop3h 19m
$235
Showing 1-10 of 41 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 August.
| 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 $394). 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 August 7, 2026.
It’s optimal to fly from Toronto to Chicago Midway Airport in the morning. By choosing this option you can save up to 26% on the cost of your flight, compared to a flight in the evening.
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 $205 and $294 in September.The cheapest round-trip price found within the last 5 days was $200 on Porter Airlines (Sep 1-Sep 20).
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 106 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.
What is the cheapest day to fly from Toronto to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Toronto to Midway. Price data was last updated on August 1, 2026.
Travelers seeking maximum savings on their Toronto to Chicago Midway Airport flight should consider departing on Monday evenings when fares are most often at their lowest. Thursday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 August 7, 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.
Entertainment
6.9
Food
7.5
Overall
8.0
Comfort
8.0
Boarding
8.2
Crew
8.6
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Entertainment
6.9
Food
7.5
Overall
8.0
Comfort
8.0
Boarding
8.2
Crew
8.6
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
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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Other flights to Midway
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Toronto and Midway flights
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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 2,558,603 searches. Data last updated August 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$168 | Average$335 | FlexibilityNo cancel fee | On-time52% |