$185+ Cheap flights from Chicago (CHI) to Saskatchewan
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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
Jul 2 — Jul 91
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Saskatchewan with Cheapflights
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Cheapest flights from Chicago to SaskatchewanExplore the most affordable flight options available from Chicago to Saskatchewan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 2, 2026.
Explore the most affordable flight options available from Chicago to Saskatchewan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 2, 2026.
This Trip.com deal was found by Cheapflights users on 5/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:30 pm
ORD
- YXE
1 stop8h 30m
WestJet
Fri 9/117:00 am
YXE
- ORD
1 stop8h 40m
WestJet
Deal found 5/31![WestJet logo]()
$374
This Trip.com deal was found by Cheapflights users on 6/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:30 pm
ORD
- YQR
1 stop6h 50m
WestJet
Fri 10/237:00 am
YQR
- ORD
1 stop8h 40m
WestJet
Deal found 6/1![WestJet logo]()
$381
This Justfly.com deal was found by Cheapflights users on 6/2. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/95:30 pm
ORD
- YXE
1 stop8h 30m
WestJet
Sun 10/117:00 am
YXE
- ORD
1 stop8h 40m
WestJet
Deal found 6/2![WestJet logo]()
$383
This Trip.com deal was found by Cheapflights users on 6/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/95:30 pm
ORD
- YXE
1 stop8h 30m
WestJet
Sat 10/1711:25 am
YXE
- ORD
1 stop28h 15m
WestJet
Deal found 6/1![WestJet logo]()
$405
This Kiwi.com deal was found by Cheapflights users on 5/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/83:20 pm
ORD
- YXE
2 stops20h 15m
Multiple Airlines
Fri 9/117:00 am
YXE
- ORD
1 stop8h 40m
Multiple Airlines
Deal found 5/31![Multiple Airlines logo]()
$408
This Trip.com deal was found by Cheapflights users on 6/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/95:30 pm
ORD
- YQR
1 stop8h 40m
WestJet
Sat 10/1711:40 am
YQR
- ORD
1 stop28h 00m
WestJet
Deal found 6/1![WestJet logo]()
$416
This Air Canada deal was found by Cheapflights users on 5/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:35 pm
ORD
- YXE
1 stop6h 41m
Air Canada
Sun 11/16:00 am
YXE
- ORD
1 stop8h 56m
Air Canada
Deal found 5/29![Air Canada logo]()
$456
This Air Canada deal was found by Cheapflights users on 5/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:45 pm
ORD
- YXE
1 stop8h 31m
Air Canada
Sun 10/46:00 am
YXE
- ORD
1 stop6h 23m
Air Canada
Deal found 5/29![Air Canada logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 5/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:30 pm
ORD
- YXE
1 stop6h 40m
Multiple Airlines
Tue 7/213:10 pm
YXE
- ORD
1 stop19h 14m
Multiple Airlines
Deal found 5/31![Multiple Airlines logo]()
$484
This Air Canada deal was found by Cheapflights users on 5/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:50 am
ORD
- YQR
1 stop10h 15m
Air Canada
Mon 9/285:45 am
YQR
- ORD
1 stop8h 10m
Air Canada
Deal found 5/28![Air Canada logo]()
$498
This Air Canada deal was found by Cheapflights users on 6/1. 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.
Thu 9/178:45 am
ORD
- YXE
2 stops15h 31m
Air Canada
Mon 9/216:00 am
YXE
- ORD
1 stop7h 55m
Air Canada
Deal found 6/1![Air Canada logo]()
$503
This oojo deal was found by Cheapflights users on 5/30. 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 8/275:30 pm
ORD
- YQR
1 stop8h 40m
WestJet
Mon 8/319:05 pm
YQR
- ORD
1 stop18h 35m
WestJet
Deal found 5/30![WestJet logo]()
$513
Best flights from Chicago to SaskatchewanDiscover carefully curated flight deals from Chicago to Saskatchewan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 2, 2026.
Discover carefully curated flight deals from Chicago to Saskatchewan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 2, 2026.
This oojo deal was found by Cheapflights users on 5/31. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/95:30 pm
ORD
- YXE
2 stops22h 15m
WestJet
Sun 10/118:50 am
YXE
- ORD
1 stop6h 50m
WestJet
Deal found 5/31![WestJet logo]()
$437
This Air Canada deal was found by Cheapflights users on 6/1. 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.
Thu 9/173:45 pm
ORD
- YXE
1 stop8h 31m
Air Canada
Mon 9/216:00 am
YXE
- ORD
1 stop6h 23m
Air Canada
Deal found 6/1![Air Canada logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 5/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/195:30 pm
ORD
- YXE
1 stop17h 05m
Multiple Airlines
Thu 7/233:10 pm
YXE
- ORD
1 stop20h 07m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$525
This FlightHub deal was found by Cheapflights users on 6/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:20 pm
ORD
- YXE
1 stop15h 18m
Porter Airlines
Sun 11/111:35 am
YXE
- ORD
1 stop7h 45m
Porter Airlines
Deal found 6/2![Porter Airlines logo]()
$535
This Delta deal was found by Cheapflights users on 6/1. 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.
Sat 9/2612:40 pm
ORD
- YXE
2 stops9h 35m
Delta
Sun 10/47:00 am
YXE
- ORD
1 stop8h 40m
Delta
Deal found 6/1![Delta logo]()
$543
This United Airlines deal was found by Cheapflights users on 5/30. 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.
Thu 6/186:00 am
ORD
- YQR
1 stop16h 30m
United Airlines
Sun 6/215:45 am
YQR
- ORD
1 stop8h 10m
United Airlines
Deal found 5/30![United Airlines logo]()
$603
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:25 am
MDW
- YXE
1 stop15h 10m
Multiple Airlines
Tue 7/711:35 am
YXE
- MDW
1 stop21h 05m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$537
This Delta deal was found by Cheapflights users on 5/29. 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 10/1711:30 am
ORD
- YXE
2 stops14h 30m
Delta
Sun 11/17:00 am
YXE
- ORD
2 stops11h 40m
Delta
Deal found 5/29![Delta logo]()
$553
This Air Canada deal was found by Cheapflights users on 6/1. 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.
Sun 11/87:15 am
ORD
- YQR
2 stops16h 04m
Air Canada
Thu 11/126:00 am
YQR
- ORD
1 stop6h 56m
Air Canada
Deal found 6/1![Air Canada logo]()
$612
This Delta deal was found by Cheapflights users on 6/1. 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.
Fri 10/91:00 pm
MDW
- YXE
2 stops11h 10m
Delta
Sat 10/176:00 am
YXE
- MDW
2 stops11h 37m
Delta
Deal found 6/1![Delta logo]()
$559
This United Airlines deal was found by Cheapflights users on 5/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/191:30 pm
ORD
- YQR
1 stop9h 00m
United Airlines
Sun 6/219:45 am
YQR
- ORD
1 stop6h 20m
United Airlines
Deal found 5/29![United Airlines logo]()
$650
This WestJet deal was found by Cheapflights users on 5/28. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:30 pm
ORD
- YQR
1 stop8h 40m
WestJet
Sun 8/166:00 am
YQR
- ORD
1 stop9h 40m
WestJet
Deal found 5/28![WestJet logo]()
$674
This Mytrip deal was found by Cheapflights users on 5/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:45 am
ORD
- YQR
3 stops14h 25m
Multiple Airlines
Mon 9/2812:45 pm
YQR
- ORD
2 stops26h 55m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$616
This Delta deal was found by Cheapflights users on 6/1. 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.
Sat 9/269:49 am
MDW
- YXE
2 stops12h 26m
Delta
Sun 10/46:00 am
YXE
- MDW
2 stops11h 33m
Delta
Deal found 6/1![Delta logo]()
$567
This Delta deal was found by Cheapflights users on 6/1. 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.
Fri 10/161:35 pm
ORD
- YQR
2 stops10h 45m
Delta
Fri 10/237:00 am
YQR
- ORD
2 stops10h 40m
Delta
Deal found 6/1![Delta logo]()
$569
This oojo deal was found by Cheapflights users on 6/1. 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.
Sat 10/176:00 am
ORD
- YQR
2 stops19h 35m
WestJet
Sun 10/1811:50 am
YQR
- ORD
2 stops27h 50m
WestJet
Deal found 6/1![WestJet logo]()
$693
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:31 pm
ORD
- YQR
1 stop23h 49m
Multiple Airlines
Sun 7/196:00 am
YQR
- ORD
1 stop9h 40m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$718
This Justfly.com deal was found by Cheapflights users on 5/31. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:30 pm
ORD
- YQR
2 stops27h 15m
WestJet
Mon 9/78:20 pm
YQR
- ORD
2 stops19h 20m
WestJet
Deal found 5/31![WestJet logo]()
$725
This Delta deal was found by Cheapflights users on 5/30. 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.
Tue 7/141:49 pm
MDW
- YXE
1 stop8h 46m
Delta
Tue 7/216:00 am
YXE
- MDW
2 stops11h 25m
Delta
Deal found 5/30![Delta logo]()
$732
Last-minute flights from Chicago to SaskatchewanDiscover last-minute flight deals from Chicago to Saskatchewan. Data last updated June 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Saskatchewan. Data last updated June 2, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/30. 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.
Mon 6/155:30 pm
ORD
- YQR
1 stop6h 50m
Delta
Fri 6/1910:45 am
YQR
- ORD
1 stop7h 46m
Delta
Deal found 5/30![Delta logo]()
$566
This Kiwi.com deal was found by Cheapflights users on 5/30. 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 6/155:30 pm
ORD
- YQR
1 stop6h 50m
Multiple Airlines
Fri 6/196:00 am
YQR
- ORD
2 stops10h 24m
Multiple Airlines
Deal found 5/30![Multiple Airlines logo]()
$601
This Air Canada deal was found by Cheapflights users on 5/30. 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.
Fri 6/198:40 pm
ORD
- YQR
1 stop13h 25m
Air Canada
Sun 6/215:45 am
YQR
- ORD
1 stop8h 10m
Air Canada
Deal found 5/30![Air Canada logo]()
$596
This Kiwi.com deal was found by Cheapflights users on 5/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/285:30 pm
ORD
- YXE
1 stop17h 05m
Multiple Airlines
Sun 7/53:10 pm
YXE
- ORD
1 stop24h 54m
Multiple Airlines
Deal found 5/31![Multiple Airlines logo]()
$594
This Kiwi.com deal was found by Cheapflights users on 5/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/295:30 pm
ORD
- YXE
1 stop8h 30m
Multiple Airlines
Sun 7/53:10 pm
YXE
- ORD
1 stop24h 54m
Multiple Airlines
Deal found 5/31![Multiple Airlines logo]()
$577
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:25 am
MDW
- YXE
1 stop15h 10m
Multiple Airlines
Tue 7/711:35 am
YXE
- MDW
1 stop21h 05m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$537
This Trip.com deal was found by Cheapflights users on 5/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:30 pm
ORD
- YQR
1 stop8h 40m
Multiple Airlines
Sun 7/1910:45 am
YQR
- ORD
2 stops33h 07m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$565
This Kiwi.com deal was found by Cheapflights users on 5/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:30 pm
ORD
- YXE
1 stop6h 40m
Multiple Airlines
Tue 7/213:10 pm
YXE
- ORD
1 stop19h 14m
Multiple Airlines
Deal found 5/31![Multiple Airlines logo]()
$484
This Expedia deal was found by Cheapflights users on 6/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:45 pm
ORD
- YXE
1 stop8h 54m
Multiple Airlines
Sat 8/157:00 am
YXE
- ORD
1 stop8h 40m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$556
This Air Canada deal was found by Cheapflights users on 5/30. 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 7/153:45 pm
ORD
- YXE
1 stop8h 54m
Air Canada
Wed 7/226:00 am
YXE
- ORD
1 stop6h 22m
Air Canada
Deal found 5/30![Air Canada logo]()
$586
This Air Canada deal was found by Cheapflights users on 5/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/169:50 am
ORD
- YXE
1 stop10h 04m
Air Canada
Mon 8/37:50 pm
YXE
- ORD
1 stop12h 10m
Air Canada
Deal found 5/31![Air Canada logo]()
$557
This Kiwi.com deal was found by Cheapflights users on 5/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/195:30 pm
ORD
- YXE
1 stop17h 05m
Multiple Airlines
Thu 7/233:10 pm
YXE
- ORD
1 stop20h 07m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$525
One-way flights from Chicago to SaskatchewanSearch for one-way flight options from Chicago to Saskatchewan. Find affordable one-way fares based on user searches. Data last updated June 2, 2026.
Search for one-way flight options from Chicago to Saskatchewan. Find affordable one-way fares based on user searches. Data last updated June 2, 2026.
This oojo deal was found by Cheapflights users on 6/1. 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.
Thu 10/155:30 pm
ORD
- YQR
1 stop6h 50m
WestJet
Deal found 6/1![WestJet logo]()
$185
This Trip.com deal was found by Cheapflights users on 5/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:39 pm
ORD
- YXE
1 stop27h 56m
Multiple Airlines
Deal found 5/31![Multiple Airlines logo]()
$227
This Trip.com deal was found by Cheapflights users on 6/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:15 am
ORD
- YQR
2 stops18h 55m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$246
This oojo deal was found by Cheapflights users on 6/1. 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.
Sun 7/195:30 pm
ORD
- YQR
2 stops18h 50m
WestJet
Deal found 6/1![WestJet logo]()
$260
This Air Canada deal was found by Cheapflights users on 5/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/273:45 pm
ORD
- YXE
1 stop8h 54m
Air Canada
Deal found 5/28![Air Canada logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 6/2. 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.
Fri 7/175:46 pm
ORD
- YQR
2 stops19h 59m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$294
This United Airlines deal was found by Cheapflights users on 5/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/157:00 am
ORD
- YXE
2 stops17h 39m
United Airlines
Deal found 5/31![United Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 5/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:11 pm
MDW
- YXE
2 stops23h 24m
Multiple Airlines
Deal found 5/31![Multiple Airlines logo]()
$340
This Air Canada deal was found by Cheapflights users on 6/2. 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.
Fri 7/178:40 pm
ORD
- YQR
1 stop13h 25m
Air Canada
Deal found 6/2![Air Canada logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/279:48 pm
ORD
- YXE
2 stops24h 47m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/275:22 pm
ORD
- YXE
3 stops20h 38m
WestJet
Deal found 5/28![WestJet logo]()
$383
This Air Canada deal was found by Cheapflights users on 5/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:40 pm
ORD
- YXE
1 stop14h 06m
Air Canada
Deal found 5/29![Air Canada logo]()
$430
Find flight deals from Chicago to Saskatchewan
Keep the following information in mind while searching for Chicago to Saskatchewan flight deals. Data was last updated June 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $374 (Trip.com) |
One-way from | $185 (oojo) |
Popular in | December |
Cheapest in | September |
Average price | $573 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Saskatchewan 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 June 2, 2026.
Use the filters below to find and compare flights from Chicago to Saskatchewan that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSaskatoon
ORD - YXE
ORDYXE
Chicago O'Hare Intl
Fri 10/9
5:30 pm-2:45 pm
2 stops22h 15m
Saskatoon
Sun 10/11
8:50 am-4:40 pm
1 stop6h 50m
$437
Quickest round-trip
ChicagoSaskatoon
ORD - YXE
ORDYXE
Chicago O'Hare Intl
Thu 9/17
3:45 pm-11:16 pm
1 stop8h 31m
Saskatoon
Mon 9/21
6:00 am-1:23 pm
1 stop6h 23m
$470
ChicagoSaskatoon
ORD - YXE
ORDYXE
Chicago O'Hare Intl
Sun 7/19
5:30 pm-9:35 am
1 stop17h 05m
Saskatoon
Thu 7/23
3:10 pm-12:17 pm
1 stop20h 07m
$525
ChicagoSaskatoon
ORD - YXE
ORDYXE
Chicago O'Hare Intl
Sat 10/17
8:20 pm-10:38 am
1 stop15h 18m
Saskatoon
Sun 11/1
11:35 am-7:20 pm
1 stop7h 45m
$535
ChicagoSaskatoon
MDW - YXE
MDWYXE
Chicago Midway
Sat 7/4
10:25 am-12:35 am
1 stop15h 10m
Saskatoon
Tue 7/7
11:35 am-9:40 am
1 stop21h 05m
$537
ChicagoSaskatoon
ORD - YXE
ORDYXE
Chicago O'Hare Intl
Sat 9/26
12:40 pm-9:15 pm
2 stops9h 35m
Saskatoon
Sun 10/4
7:00 am-4:40 pm
1 stop8h 40m
$543
ChicagoSaskatoon
ORD - YXE
ORDYXE
Chicago O'Hare Intl
Sat 10/17
11:30 am-1:00 am
2 stops14h 30m
Saskatoon
Sun 11/1
7:00 am-6:40 pm
2 stops11h 40m
$553
ChicagoSaskatoon
MDW - YXE
MDWYXE
Chicago Midway
Fri 10/9
1:00 pm-11:10 pm
2 stops11h 10m
Saskatoon
Sat 10/17
6:00 am-6:37 pm
2 stops11h 37m
$559
ChicagoSaskatoon
MDW - YXE
MDWYXE
Chicago Midway
Sat 9/26
9:49 am-9:15 pm
2 stops12h 26m
Saskatoon
Sun 10/4
6:00 am-6:33 pm
2 stops11h 33m
$567
ChicagoRegina
ORD - YQR
ORDYQR
Chicago O'Hare Intl
Fri 10/16
1:35 pm-11:20 pm
2 stops10h 45m
Regina
Fri 10/23
7:00 am-6:40 pm
2 stops10h 40m
$569
Showing 1-10 of 35 resultsSorted by cheapest first
Best time to book a flight from Chicago to Saskatchewan
Have a flexible travel schedule? Discover the best time to fly to Saskatchewan from Chicago with our price prediction graph.
ORD-YQR
ORD-YXE
MDW-YXE
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 Saskatchewan
CHI-CASK
ORD-YQR
ORD-YXE
MDW-YXE
How much does it cost to fly round-trip from Chicago to Saskatchewan?
Reviews of airlines servicing Saskatchewan
Get insights into the airlines that provide service to Saskatchewan. 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 Saskatchewan. Reviews last updated June 2, 2026.
Get a feel of what it's like to fly with Delta,WestJet, andAir Canada from Chicago to Saskatchewan by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
7.8
Overall
7.9
Crew
8.5
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Comfort
7.8
Overall
7.9
Crew
8.5
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Comfort
7.8
Overall
7.9
Crew
8.5
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Comfort
7.8
Overall
7.9
Crew
8.5
Food
7.2
Entertainment
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 Chicago to Saskatchewan. 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 Saskatchewan
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Saskatchewan by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Saskatchewan by cabin class
Find flights from Chicago to Saskatchewan, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Saskatchewan flights
Browse other Chicago and Saskatchewan flight options. Last updated on June 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Chicago to Saskatchewan
Discover the top 4 airlines that operate flights from Chicago to Saskatchewan. 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 June 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$609 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$175 | Average$542 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$198 | Average$367 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$213 | Average$770 | FlexibilityNo cancel fee | On-time69% |