$184+ Cheap flights from Chicago (CHI) to Prince Edward Island
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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYG
Jun 4 — Jun 111
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Prince Edward Island 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 Chicago to Prince Edward IslandExplore the most affordable flight options available from Chicago to Prince Edward Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
Explore the most affordable flight options available from Chicago to Prince Edward Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Mon 5/2510:30 am
MDW
- YQM
1 stop22h 42m
Porter Airlines
Sun 5/316:15 am
YQM
- MDW
1 stop29h 20m
Porter Airlines
Deal found 5/3![Porter Airlines logo]()
$471
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/143:20 pm
MDW
- YQM
1 stop17h 55m
Porter Airlines
Sun 6/216:15 am
YQM
- MDW
1 stop5h 25m
Porter Airlines
Deal found 4/30![Porter Airlines logo]()
$522
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Thu 6/183:20 pm
MDW
- YQM
1 stop17h 55m
Porter Airlines
Thu 6/256:15 am
YQM
- MDW
1 stop5h 25m
Porter Airlines
Deal found 5/3![Porter Airlines logo]()
$527
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:30 am
MDW
- YYG
1 stop22h 25m
Multiple Airlines
Thu 6/45:15 pm
YYG
- MDW
2 stops42h 20m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$587
This Air Canada deal was found by Cheapflights users on 4/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:45 am
ORD
- YYG
1 stop4h 55m
Air Canada
Tue 9/2211:20 am
YYG
- ORD
1 stop5h 32m
Air Canada
Deal found 4/30![Air Canada logo]()
$617
This Air Canada deal was found by Cheapflights users on 4/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/168:45 am
ORD
- YYG
1 stop4h 55m
Air Canada
Thu 8/204:30 pm
YYG
- ORD
1 stop5h 35m
Air Canada
Deal found 4/30![Air Canada logo]()
$647
This Air Canada deal was found by Cheapflights users on 5/3. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:45 am
ORD
- YYG
1 stop4h 55m
Air Canada
Sun 9/204:30 pm
YYG
- ORD
1 stop5h 42m
Air Canada
Deal found 5/3![Air Canada logo]()
$649
This Air Canada deal was found by Cheapflights users on 5/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/293:50 pm
ORD
- YYG
1 stop6h 12m
Air Canada
Fri 6/511:20 am
YYG
- ORD
1 stop5h 30m
Air Canada
Deal found 5/1![Air Canada logo]()
$652
This Mytrip deal was found by Cheapflights users on 5/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:25 am
MDW
- YQM
1 stop22h 47m
Porter Airlines
Tue 8/186:15 am
YQM
- MDW
1 stop5h 25m
Porter Airlines
Deal found 5/3![Porter Airlines logo]()
$670
This Air Canada deal was found by Cheapflights users on 5/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/38:45 am
ORD
- YYG
1 stop4h 55m
Air Canada
Sat 8/87:00 pm
YYG
- ORD
1 stop16h 00m
Air Canada
Deal found 5/1![Air Canada logo]()
$677
This Air Canada deal was found by Cheapflights users on 5/4. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/168:45 am
ORD
- YYG
1 stop4h 55m
Air Canada
Sat 8/224:30 pm
YYG
- ORD
1 stop5h 35m
Air Canada
Deal found 5/4![Air Canada logo]()
$679
This Air Canada deal was found by Cheapflights users on 5/3. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:45 am
ORD
- YYG
1 stop4h 55m
Air Canada
Wed 6/2412:30 pm
YYG
- ORD
1 stop6h 27m
Air Canada
Deal found 5/3![Air Canada logo]()
$684
Best flights from Chicago to Prince Edward IslandDiscover carefully curated flight deals from Chicago to Prince Edward Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
Discover carefully curated flight deals from Chicago to Prince Edward Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Mon 5/2510:30 am
MDW
- YQM
1 stop22h 42m
Porter Airlines
Sun 5/316:15 am
YQM
- MDW
1 stop29h 20m
Porter Airlines
Deal found 5/3![Porter Airlines logo]()
$471
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:30 am
MDW
- YYG
1 stop22h 25m
Multiple Airlines
Thu 6/45:15 pm
YYG
- MDW
2 stops42h 20m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$587
This Air Canada deal was found by Cheapflights users on 4/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:45 am
ORD
- YYG
1 stop4h 55m
Air Canada
Sun 9/204:30 pm
YYG
- ORD
1 stop5h 42m
Air Canada
Deal found 4/30![Air Canada logo]()
$617
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/109:19 pm
ORD
- YYG
2 stops16h 22m
United Airlines
Sun 6/145:15 am
YYG
- ORD
1 stop5h 45m
United Airlines
Deal found 4/30![United Airlines logo]()
$758
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/143:20 pm
MDW
- YQM
1 stop17h 55m
Porter Airlines
Sun 6/216:15 am
YQM
- MDW
1 stop5h 25m
Porter Airlines
Deal found 4/30![Porter Airlines logo]()
$522
This Air Canada deal was found by Cheapflights users on 4/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:45 am
ORD
- YYG
1 stop4h 55m
Air Canada
Thu 9/244:30 pm
YYG
- ORD
1 stop5h 42m
Air Canada
Deal found 4/30![Air Canada logo]()
$617
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Thu 6/183:20 pm
MDW
- YQM
1 stop17h 55m
Porter Airlines
Thu 6/2511:55 am
YQM
- MDW
2 stops23h 45m
Porter Airlines
Deal found 5/3![Porter Airlines logo]()
$611
This Air Canada deal was found by Cheapflights users on 5/3. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/168:45 am
ORD
- YYG
1 stop4h 55m
Air Canada
Sat 8/224:30 pm
YYG
- ORD
1 stop5h 35m
Air Canada
Deal found 5/3![Air Canada logo]()
$679
This Mytrip deal was found by Cheapflights users on 5/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:25 am
MDW
- YQM
1 stop22h 47m
Porter Airlines
Tue 8/186:15 am
YQM
- MDW
1 stop5h 25m
Porter Airlines
Deal found 5/3![Porter Airlines logo]()
$670
This Air Canada deal was found by Cheapflights users on 5/3. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:45 am
ORD
- YYG
1 stop4h 55m
Air Canada
Wed 6/2412:30 pm
YYG
- ORD
1 stop6h 27m
Air Canada
Deal found 5/3![Air Canada logo]()
$684
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/149:17 am
MDW
- YQM
3 stops34h 21m
Multiple Airlines
Sun 6/2111:55 am
YQM
- MDW
3 stops23h 19m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$851
This oojo deal was found by Cheapflights users on 5/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/203:20 pm
MDW
- YYG
2 stops23h 15m
Porter Airlines
Sun 5/245:20 pm
YYG
- MDW
2 stops18h 25m
Porter Airlines
Deal found 5/1![Porter Airlines logo]()
$731
This Mytrip deal was found by Cheapflights users on 5/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/193:20 pm
MDW
- YYG
2 stops17h 50m
Multiple Airlines
Wed 8/2611:40 am
YYG
- MDW
2 stops8h 51m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$932
This oojo deal was found by Cheapflights users on 5/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2110:25 am
MDW
- YYG
2 stops28h 10m
Porter Airlines
Tue 7/2811:50 am
YYG
- MDW
2 stops23h 50m
Porter Airlines
Deal found 5/1![Porter Airlines logo]()
$739
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/101:21 pm
MDW
- YYG
3 stops25h 14m
Multiple Airlines
Sun 6/145:15 pm
YYG
- MDW
2 stops18h 20m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$936
This oojo deal was found by Cheapflights users on 5/3. 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.
Wed 6/1710:15 am
MDW
- YYG
2 stops28h 20m
Porter Airlines
Wed 6/2411:50 am
YYG
- MDW
2 stops28h 45m
Porter Airlines
Deal found 5/3![Porter Airlines logo]()
$740
This Porter Airlines deal was found by Cheapflights users on 4/30. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am
ORD
- YYG
2 stops7h 35m
Porter Airlines
Thu 9/245:20 pm
YYG
- ORD
2 stops19h 40m
Porter Airlines
Deal found 4/30![Porter Airlines logo]()
$757
This Mytrip deal was found by Cheapflights users on 5/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:25 am
MDW
- YQM
2 stops9h 05m
Multiple Airlines
Tue 8/186:15 am
YQM
- MDW
3 stops14h 18m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$1,121
This oojo deal was found by Cheapflights users on 4/30. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/143:20 pm
MDW
- YYG
2 stops23h 15m
Porter Airlines
Sun 6/215:20 pm
YYG
- MDW
2 stops23h 15m
Porter Airlines
Deal found 4/30![Porter Airlines logo]()
$799
This oojo deal was found by Cheapflights users on 5/2. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/910:25 am
MDW
- YYG
2 stops28h 10m
Porter Airlines
Thu 8/1311:50 am
YYG
- MDW
2 stops23h 50m
Porter Airlines
Deal found 5/2![Porter Airlines logo]()
$840
This oojo deal was found by Cheapflights users on 4/30. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1010:15 am
MDW
- YYG
2 stops28h 20m
Porter Airlines
Sun 6/145:15 pm
YYG
- MDW
2 stops23h 20m
Porter Airlines
Deal found 4/30![Porter Airlines logo]()
$870
This Porter Airlines deal was found by Cheapflights users on 5/3. 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.
Sat 8/1510:25 am
MDW
- YYG
2 stops28h 10m
Porter Airlines
Tue 8/1811:50 am
YYG
- MDW
2 stops28h 45m
Porter Airlines
Deal found 5/3![Porter Airlines logo]()
$897
Last-minute flights from Chicago to Prince Edward IslandDiscover last-minute flight deals from Chicago to Prince Edward Island. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Prince Edward Island. Data last updated May 5, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 4/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:45 am
ORD
- YYG
1 stop4h 56m
Air Canada
Thu 5/144:30 pm
YYG
- ORD
1 stop5h 38m
Air Canada
Deal found 4/30![Air Canada logo]()
$733
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Wed 5/2010:30 am
MDW
- YYG
2 stops28h 05m
Multiple Airlines
Sun 5/2411:40 am
YYG
- MDW
1 stop24h 05m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$684
This oojo deal was found by Cheapflights users on 5/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/203:20 pm
MDW
- YYG
2 stops23h 15m
Porter Airlines
Sun 5/245:20 pm
YYG
- MDW
2 stops18h 25m
Porter Airlines
Deal found 5/1![Porter Airlines logo]()
$731
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Mon 5/2510:30 am
MDW
- YQM
1 stop22h 42m
Porter Airlines
Sun 5/316:15 am
YQM
- MDW
1 stop29h 20m
Porter Airlines
Deal found 5/3![Porter Airlines logo]()
$471
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:30 am
MDW
- YYG
1 stop22h 25m
Multiple Airlines
Thu 6/45:15 pm
YYG
- MDW
2 stops42h 20m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$587
This Air Canada deal was found by Cheapflights users on 4/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:45 am
ORD
- YYG
1 stop4h 56m
Air Canada
Thu 6/411:20 am
YYG
- ORD
1 stop5h 30m
Air Canada
Deal found 4/30![Air Canada logo]()
$647
This oojo deal was found by Cheapflights users on 4/30. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/283:20 pm
MDW
- YYG
2 stops23h 15m
Porter Airlines
Thu 6/45:15 pm
YYG
- MDW
2 stops18h 20m
Porter Airlines
Deal found 4/30![Porter Airlines logo]()
$705
This FlightHub deal was found by Cheapflights users on 4/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:30 pm
ORD
- YYG
1 stop21h 40m
Multiple Airlines
Thu 6/45:15 pm
YYG
- ORD
2 stops17h 20m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$730
This Air Canada deal was found by Cheapflights users on 5/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/293:50 pm
ORD
- YYG
1 stop6h 12m
Air Canada
Fri 6/511:20 am
YYG
- ORD
1 stop5h 30m
Air Canada
Deal found 5/1![Air Canada logo]()
$652
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/143:20 pm
MDW
- YQM
1 stop17h 55m
Porter Airlines
Sun 6/216:15 am
YQM
- MDW
1 stop5h 25m
Porter Airlines
Deal found 4/30![Porter Airlines logo]()
$522
This Air Canada deal was found by Cheapflights users on 5/3. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:45 am
ORD
- YYG
1 stop4h 55m
Air Canada
Wed 6/2412:30 pm
YYG
- ORD
1 stop6h 27m
Air Canada
Deal found 5/3![Air Canada logo]()
$684
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Thu 6/183:20 pm
MDW
- YQM
1 stop17h 55m
Porter Airlines
Thu 6/256:15 am
YQM
- MDW
1 stop5h 25m
Porter Airlines
Deal found 5/3![Porter Airlines logo]()
$527
One-way flights from Chicago to Prince Edward IslandSearch for one-way flight options from Chicago to Prince Edward Island. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
Search for one-way flight options from Chicago to Prince Edward Island. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:30 am
MDW
- YYG
1 stop22h 25m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/313:20 pm
MDW
- YQM
1 stop17h 55m
Porter Airlines
Deal found 5/1![Porter Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1610:15 am
MDW
- YQM
1 stop23h 00m
Porter Airlines
Deal found 5/2![Porter Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/1510:15 am
MDW
- YQM
2 stops9h 23m
Porter Airlines
Deal found 4/30![Porter Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:30 pm
ORD
- YYG
2 stops15h 25m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1612:27 pm
MDW
- YQM
3 stops44h 48m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$298
This Air Canada deal was found by Cheapflights users on 5/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:45 am
ORD
- YYG
1 stop4h 56m
Air Canada
Deal found 5/2![Air Canada logo]()
$317
This oojo deal was found by Cheapflights users on 5/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/1510:15 am
MDW
- YYG
2 stops28h 20m
Porter Airlines
Deal found 5/1![Porter Airlines logo]()
$326
This Air Canada deal was found by Cheapflights users on 5/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/158:20 pm
ORD
- YYG
1 stop13h 15m
Air Canada
Deal found 5/1![Air Canada logo]()
$333
This Mytrip deal was found by Cheapflights users on 5/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/283:20 pm
MDW
- YYG
2 stops23h 15m
Porter Airlines
Deal found 5/2![Porter Airlines logo]()
$341
This Air Canada deal was found by Cheapflights users on 5/4. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/178:45 am
ORD
- YYG
1 stop4h 55m
Air Canada
Deal found 5/4![Air Canada logo]()
$347
This United Airlines deal was found by Cheapflights users on 5/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/159:55 pm
ORD
- YYG
2 stops15h 46m
United Airlines
Deal found 5/1![United Airlines logo]()
$359
Find flight deals from Chicago to Prince Edward Island
Keep the following information in mind while searching for Chicago to Prince Edward Island flight deals. Data was last updated May 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $471 (Kiwi.com) |
One-way from | $184 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Prince Edward Island 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 May 5, 2026.
Use the filters below to find and compare flights from Chicago to Prince Edward Island that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMoncton
MDW - YQM
MDWYQM
Chicago Midway
Mon 5/25
10:30 am-11:12 am
1 stop22h 42m
Moncton Intl
Sun 5/31
6:15 am-9:35 am
1 stop29h 20m
$471
ChicagoMoncton
MDW - YQM
MDWYQM
Chicago Midway
Sun 6/14
3:20 pm-11:15 am
1 stop17h 55m
Moncton Intl
Sun 6/21
6:15 am-9:40 am
1 stop5h 25m
$522
ChicagoCharlottetown
MDW - YYG
MDWYYG
Chicago Midway
Thu 5/28
10:30 am-10:55 am
1 stop22h 25m
Charlottetown
Thu 6/4
5:15 pm-9:35 am
2 stops42h 20m
$587
ChicagoMoncton
MDW - YQM
MDWYQM
Chicago Midway
Thu 6/18
3:20 pm-11:15 am
1 stop17h 55m
Moncton Intl
Thu 6/25
11:55 am-9:40 am
2 stops23h 45m
$611
ChicagoCharlottetown
ORD - YYG
ORDYYG
Chicago O'Hare Intl
Wed 9/16
8:45 am-3:40 pm
1 stop4h 55m
Charlottetown
Sun 9/20
4:30 pm-8:12 pm
1 stop5h 42m
$617
ChicagoCharlottetown
ORD - YYG
ORDYYG
Chicago O'Hare Intl
Mon 9/21
8:45 am-3:40 pm
1 stop4h 55m
Charlottetown
Thu 9/24
4:30 pm-8:12 pm
1 stop5h 42m
$617
ChicagoMoncton
MDW - YQM
MDWYQM
Chicago Midway
Sat 8/15
10:25 am-11:12 am
1 stop22h 47m
Moncton Intl
Tue 8/18
6:15 am-9:40 am
1 stop5h 25m
$670
Quickest round-trip
ChicagoCharlottetown
ORD - YYG
ORDYYG
Chicago O'Hare Intl
Sun 8/16
8:45 am-3:40 pm
1 stop4h 55m
Charlottetown
Sat 8/22
4:30 pm-8:05 pm
1 stop5h 35m
$679
ChicagoCharlottetown
ORD - YYG
ORDYYG
Chicago O'Hare Intl
Wed 6/17
8:45 am-3:40 pm
1 stop4h 55m
Charlottetown
Wed 6/24
12:30 pm-4:57 pm
1 stop6h 27m
$684
ChicagoCharlottetown
MDW - YYG
MDWYYG
Chicago Midway
Wed 5/20
3:20 pm-4:35 pm
2 stops23h 15m
Charlottetown
Sun 5/24
5:20 pm-9:45 am
2 stops18h 25m
$731
Showing 1-10 of 37 resultsSorted by cheapest first
Best time to book a flight from Chicago to Prince Edward Island
Have a flexible travel schedule? Discover the best time to fly to Prince Edward Island from Chicago with our price prediction graph.
MDW-YQM
MDW-YYG
ORD-YYG
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 to Prince Edward Island
CHI-CAPE
MDW-YQM
MDW-YYG
ORD-YYG
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Prince Edward Island
Get insights into the airlines that provide service to Prince Edward Island. 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 Prince Edward Island. Reviews last updated May 5, 2026.
Peruse reviews from past customers who have flown with United Airlines and Air Canada from Chicago to Prince Edward Island to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Food
6.6
Crew
8.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Food
6.6
Crew
8.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Food
6.6
Crew
8.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Related info for your journey
Find useful and relevant information for your journey from Chicago to Prince Edward Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Prince Edward Island
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Complete your trip
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Chicago and Prince Edward Island flights
Browse other Chicago and Prince Edward Island flight options. Last updated on May 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Prince Edward Island
Discover the top 2 airlines that operate flights from Chicago to Prince Edward Island. 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 May 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$236 | Average$653 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$241 | Average$782 | FlexibilityNo cancel fee | On-time69% |