$111+ Cheap flights from Midway (MDW) to Pearson Intl (YYZ)
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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YYZ
Aug 31 — Sep 71
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Pearson Intl 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
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Cheapest flights from Midway to Pearson IntlExplore the most affordable flight options available from Midway to Pearson Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2026.
Explore the most affordable flight options available from Midway to Pearson Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2026.
This Kissandfly.com deal was found by Cheapflights users on 7/31. 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.
Thu 8/279:24 am
MDW
- YYZ
1 stop7h 00m
KLM
Sun 8/306:10 am
YYZ
- MDW
1 stop7h 29m
KLM
Deal found 7/31![KLM logo]()
$258
This Delta deal was found by Cheapflights users on 7/31. 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 8/221:25 pm
MDW
- YYZ
1 stop8h 34m
Delta
Wed 9/212:09 pm
YYZ
- MDW
1 stop5h 50m
Delta
Deal found 7/31![Delta logo]()
$266
This Delta deal was found by Cheapflights users on 7/29. 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 9/125:37 pm
MDW
- YYZ
1 stop4h 22m
Delta
Tue 9/156:00 am
YYZ
- MDW
1 stop7h 39m
Delta
Deal found 7/29![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 7/31. 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 8/219:24 am
MDW
- YYZ
1 stop4h 56m
Delta
Sun 8/2312:09 pm
YYZ
- MDW
1 stop7h 24m
Delta
Deal found 7/31![Delta logo]()
$300
This Delta deal was found by Cheapflights users on 7/29. 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 9/99:29 am
MDW
- YYZ
1 stop6h 51m
Delta
Mon 9/2112:08 pm
YYZ
- MDW
1 stop7h 25m
Delta
Deal found 7/29![Delta logo]()
$307
This Delta deal was found by Cheapflights users on 8/1. 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 8/196:42 pm
MDW
- YYZ
1 stop3h 21m
Delta
Sat 8/2212:09 pm
YYZ
- MDW
1 stop7h 24m
Delta
Deal found 8/1![Delta logo]()
$318
This Delta deal was found by Cheapflights users on 7/30. 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.
Sun 8/231:25 pm
MDW
- YYZ
1 stop8h 38m
Delta
Tue 9/19:45 am
YYZ
- MDW
1 stop8h 14m
Delta
Deal found 7/30![Delta logo]()
$328
This Kissandfly.com deal was found by Cheapflights users on 7/31. 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.
Fri 8/219:24 am
MDW
- YYZ
1 stop7h 00m
KLM
Sun 8/236:10 am
YYZ
- MDW
1 stop7h 29m
KLM
Deal found 7/31![KLM logo]()
$330
This Delta deal was found by Cheapflights users on 7/31. 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 8/246:42 pm
MDW
- YYZ
1 stop3h 21m
Delta
Thu 9/36:10 am
YYZ
- MDW
1 stop7h 29m
Delta
Deal found 7/31![Delta logo]()
$332
This Delta deal was found by Cheapflights users on 7/31. 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 8/209:24 am
MDW
- YYZ
1 stop7h 00m
Delta
Sat 8/296:10 am
YYZ
- MDW
1 stop7h 29m
Delta
Deal found 7/31![Delta logo]()
$337
This Delta deal was found by Cheapflights users on 7/31. 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 12/126:44 pm
MDW
- YYZ
1 stop3h 13m
Delta
Wed 12/309:45 am
YYZ
- MDW
1 stop7h 37m
Delta
Deal found 7/31![Delta logo]()
$340
Best flights from Midway to Pearson IntlDiscover carefully curated flight deals from Midway to Pearson Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 1, 2026.
Discover carefully curated flight deals from Midway to Pearson Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 1, 2026.
This Delta deal was found by Cheapflights users on 7/30. 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 8/291:25 pm
MDW
- YYZ
1 stop8h 34m
Delta
Sat 9/59:45 am
YYZ
- MDW
1 stop8h 14m
Delta
Deal found 7/30![Delta logo]()
$266
This Delta deal was found by Cheapflights users on 7/31. 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 9/149:24 am
MDW
- YYZ
1 stop6h 56m
Delta
Wed 9/2312:08 pm
YYZ
- MDW
1 stop7h 25m
Delta
Deal found 7/31![Delta logo]()
$266
This Delta deal was found by Cheapflights users on 7/31. 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 8/261:25 pm
MDW
- YYZ
1 stop8h 38m
Delta
Fri 8/286:10 am
YYZ
- MDW
1 stop4h 07m
Delta
Deal found 7/31![Delta logo]()
$266
This Delta deal was found by Cheapflights users on 7/29. 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 9/31:25 pm
MDW
- YYZ
1 stop8h 38m
Delta
Sun 9/69:45 am
YYZ
- MDW
1 stop8h 14m
Delta
Deal found 7/29![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 7/27. 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 9/115:03 pm
MDW
- YYZ
1 stop4h 56m
Delta
Fri 9/1812:08 pm
YYZ
- MDW
1 stop7h 25m
Delta
Deal found 7/27![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 7/29. 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 9/125:37 pm
MDW
- YYZ
1 stop4h 22m
Delta
Sat 9/196:00 am
YYZ
- MDW
1 stop7h 39m
Delta
Deal found 7/29![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 7/31. 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 9/31:25 pm
MDW
- YYZ
1 stop8h 38m
Delta
Tue 9/86:00 am
YYZ
- MDW
1 stop4h 07m
Delta
Deal found 7/31![Delta logo]()
$300
This Delta deal was found by Cheapflights users on 7/28. 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 8/259:24 am
MDW
- YYZ
1 stop4h 56m
Delta
Tue 9/112:09 pm
YYZ
- MDW
1 stop5h 50m
Delta
Deal found 7/28![Delta logo]()
$307
This Delta deal was found by Cheapflights users on 7/28. 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 9/29:24 am
MDW
- YYZ
1 stop7h 00m
Delta
Sat 9/512:09 pm
YYZ
- MDW
1 stop5h 50m
Delta
Deal found 7/28![Delta logo]()
$307
This Delta deal was found by Cheapflights users on 7/30. 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 9/49:24 am
MDW
- YYZ
1 stop7h 00m
Delta
Mon 9/76:10 am
YYZ
- MDW
1 stop7h 29m
Delta
Deal found 7/30![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 7/29. 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 9/125:37 pm
MDW
- YYZ
1 stop4h 22m
Delta
Thu 9/1712:08 pm
YYZ
- MDW
1 stop7h 25m
Delta
Deal found 7/29![Delta logo]()
$328
Last-minute flights from Midway to Pearson IntlDiscover last-minute flight deals from Midway to Pearson Intl. Data last updated August 1, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Pearson Intl. Data last updated August 1, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/29. 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 8/151:25 pm
MDW
- YYZ
1 stop8h 34m
Delta
Thu 8/206:10 am
YYZ
- MDW
1 stop7h 29m
Delta
Deal found 7/29![Delta logo]()
$346
This Delta deal was found by Cheapflights users on 7/31. 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 8/189:24 am
MDW
- YYZ
1 stop7h 00m
Delta
Sun 8/2312:09 pm
YYZ
- MDW
1 stop7h 24m
Delta
Deal found 7/31![Delta logo]()
$353
This Delta deal was found by Cheapflights users on 8/1. 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 8/196:42 pm
MDW
- YYZ
1 stop3h 21m
Delta
Sat 8/2212:09 pm
YYZ
- MDW
1 stop7h 24m
Delta
Deal found 8/1![Delta logo]()
$318
This Delta deal was found by Cheapflights users on 7/31. 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 8/209:24 am
MDW
- YYZ
1 stop7h 00m
Delta
Sat 8/296:10 am
YYZ
- MDW
1 stop7h 29m
Delta
Deal found 7/31![Delta logo]()
$337
This Delta deal was found by Cheapflights users on 7/31. 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 8/219:24 am
MDW
- YYZ
1 stop4h 56m
Delta
Sun 8/2312:09 pm
YYZ
- MDW
1 stop7h 24m
Delta
Deal found 7/31![Delta logo]()
$300
This Kissandfly.com deal was found by Cheapflights users on 7/31. 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.
Fri 8/219:24 am
MDW
- YYZ
1 stop7h 00m
KLM
Sun 8/236:10 am
YYZ
- MDW
1 stop7h 29m
KLM
Deal found 7/31![KLM logo]()
$330
This Delta deal was found by Cheapflights users on 7/31. 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 8/221:25 pm
MDW
- YYZ
1 stop8h 34m
Delta
Wed 9/212:09 pm
YYZ
- MDW
1 stop5h 50m
Delta
Deal found 7/31![Delta logo]()
$266
This Delta deal was found by Cheapflights users on 7/30. 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.
Sun 8/231:25 pm
MDW
- YYZ
1 stop8h 38m
Delta
Tue 9/19:45 am
YYZ
- MDW
1 stop8h 14m
Delta
Deal found 7/30![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 7/31. 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 8/246:42 pm
MDW
- YYZ
1 stop3h 21m
Delta
Thu 9/36:10 am
YYZ
- MDW
1 stop7h 29m
Delta
Deal found 7/31![Delta logo]()
$332
This Delta deal was found by Cheapflights users on 7/28. 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 8/259:24 am
MDW
- YYZ
1 stop4h 56m
Delta
Tue 9/112:09 pm
YYZ
- MDW
1 stop5h 50m
Delta
Deal found 7/28![Delta logo]()
$307
This Kissandfly.com deal was found by Cheapflights users on 7/31. 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.
Thu 8/279:24 am
MDW
- YYZ
1 stop7h 00m
KLM
Sun 8/306:10 am
YYZ
- MDW
1 stop7h 29m
KLM
Deal found 7/31![KLM logo]()
$258
One-way flights from Midway to Pearson IntlSearch for one-way flight options from Midway to Pearson Intl. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
Search for one-way flight options from Midway to Pearson Intl. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
This Delta deal was found by Cheapflights users on 7/28. 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 9/125:37 pm
MDW
- YYZ
1 stop4h 22m
Delta
Deal found 7/28![Delta logo]()
$111
This Delta deal was found by Cheapflights users on 7/30. 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 9/109:29 am
MDW
- YYZ
1 stop6h 51m
Delta
Deal found 7/30![Delta logo]()
$121
This Kissandfly.com deal was found by Cheapflights users on 7/30. 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.
Tue 9/159:29 am
MDW
- YYZ
1 stop6h 51m
KLM
Deal found 7/30![KLM logo]()
$126
This Delta deal was found by Cheapflights users on 7/29. 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 8/279:24 am
MDW
- YYZ
1 stop7h 00m
Delta
Deal found 7/29![Delta logo]()
$139
This Delta deal was found by Cheapflights users on 7/30. 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 8/201:25 pm
MDW
- YYZ
1 stop8h 38m
Delta
Deal found 7/30![Delta logo]()
$149
This Delta deal was found by Cheapflights users on 7/29. 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 8/121:25 pm
MDW
- YYZ
1 stop8h 38m
Delta
Deal found 7/29![Delta logo]()
$150
This Delta deal was found by Cheapflights users on 7/31. 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 8/159:24 am
MDW
- YYZ
1 stop7h 00m
Delta
Deal found 7/31![Delta logo]()
$157
This Kissandfly.com deal was found by Cheapflights users on 7/29. 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.
Tue 8/189:24 am
MDW
- YYZ
1 stop4h 56m
KLM
Deal found 7/29![KLM logo]()
$158
This Delta deal was found by Cheapflights users on 7/29. 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 8/171:25 pm
MDW
- YYZ
1 stop8h 38m
Delta
Deal found 7/29![Delta logo]()
$167
This Delta deal was found by Cheapflights users on 7/28. 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.
Sun 8/169:24 am
MDW
- YYZ
1 stop7h 00m
Delta
Deal found 7/28![Delta logo]()
$169
This Delta deal was found by Cheapflights users on 7/30. 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.
Sun 9/136:40 pm
MDW
- YYZ
1 stop3h 19m
Delta
Deal found 7/30![Delta logo]()
$182
Find flight deals from Midway to Pearson Intl
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Pearson Intl (YYZ). 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 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $258 (Kissandfly.com) |
One-way from | $111 (Delta) |
Popular in | September |
Cheapest in | July |
Average price | $455 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Pearson Intl 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 1, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Toronto Pearson Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Sat 8/29
1:25 pm-10:59 pm
1 stop8h 34m
Toronto Pearson Intl
Sat 9/5
9:45 am-4:59 pm
1 stop8h 14m
$266
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Mon 9/14
9:24 am-5:20 pm
1 stop6h 56m
Toronto Pearson Intl
Wed 9/23
12:08 pm-6:33 pm
1 stop7h 25m
$266
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Wed 8/26
1:25 pm-11:03 pm
1 stop8h 38m
Toronto Pearson Intl
Fri 8/28
6:10 am-9:17 am
1 stop4h 07m
$266
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Thu 9/3
1:25 pm-11:03 pm
1 stop8h 38m
Toronto Pearson Intl
Sun 9/6
9:45 am-4:59 pm
1 stop8h 14m
$279
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Fri 9/11
5:03 pm-10:59 pm
1 stop4h 56m
Toronto Pearson Intl
Fri 9/18
12:08 pm-6:33 pm
1 stop7h 25m
$279
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Sat 9/12
5:37 pm-10:59 pm
1 stop4h 22m
Toronto Pearson Intl
Sat 9/19
6:00 am-12:39 pm
1 stop7h 39m
$279
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Thu 9/3
1:25 pm-11:03 pm
1 stop8h 38m
Toronto Pearson Intl
Tue 9/8
6:00 am-9:07 am
1 stop4h 07m
$300
Quickest round-trip
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Tue 8/25
9:24 am-3:20 pm
1 stop4h 56m
Toronto Pearson Intl
Tue 9/1
12:09 pm-4:59 pm
1 stop5h 50m
$307
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Wed 9/2
9:24 am-5:24 pm
1 stop7h 00m
Toronto Pearson Intl
Sat 9/5
12:09 pm-4:59 pm
1 stop5h 50m
$307
ChicagoToronto
MDW - YYZ
MDWYYZ
Chicago Midway
Fri 9/4
9:24 am-5:24 pm
1 stop7h 00m
Toronto Pearson Intl
Mon 9/7
6:10 am-12:39 pm
1 stop7h 29m
$328
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from Midway to Pearson Intl
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 Midway to Pearson Intl in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Toronto Pearson Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Toronto Pearson Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Toronto Pearson Intl Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Toronto Pearson Intl 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 Chicago Midway Airport-Toronto Pearson Intl 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 Midway to Pearson Intl
Have a flexible travel schedule? Discover the best time to fly to Pearson Intl from Midway with our price prediction graph.
MDW-YYZ
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 Chicago Midway Airport to Toronto Pearson Intl Airport
Prices
Delays
How often are flights from Chicago to Toronto delayed?
About 19% of weekly flights between Chicago and Toronto have experienced delays in the past year, with the average delay time being 85 minutes.
What is the most punctual flight time for Chicago to Toronto flights?
Historically, flights departing in the evening 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?
Saturday tends to have the lowest number of delays on this route, whereas Thursday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Toronto flights?
Over the last year, Air Canada have had the lowest number of delays on this route, with just 24% of flights being delayed.
Reviews of airlines servicing Pearson Intl
Get insights into the airlines that provide service to Pearson Intl. 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 Pearson Intl. Reviews last updated August 1, 2026.
See what other customers who have flown with Delta from Chicago Midway Airport to Toronto Pearson Intl Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Food
7.2
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Overall
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Food
7.2
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Overall
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from Midway to Pearson Intl. 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 Toronto Pearson Intl Airport?
Book flights to Toronto Pearson Intl Airport if you plan to visit one of these locationsMarkham
Brampton
Collingwood
Vaughan
Pickering
Oakville
Kitchener
Cambridge
Whitby
Owen Sound
Burlington
Ajax
Orillia
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Midway and Pearson Intl flights
Browse other Midway and Pearson Intl flight options. Last updated on August 1, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on August 1, 2026.
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Top airline flying from Midway to Pearson Intl
Discover the top airline that operate flights from Midway to Pearson Intl. 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 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$359 | FlexibilityNo cancel fee | On-timeN/A |