$146+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
May 3 — May 101
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Saskatchewan with Cheapflights
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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 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 April 3, 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 April 3, 2026.
This Trip.com deal was found by Cheapflights users on 3/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:30 pm
ORD
- YXE
1 stop6h 40m
WestJet
Sun 5/38:50 am
YXE
- ORD
1 stop6h 50m
WestJet
Deal found 3/28![WestJet logo]()
$291
This Trip.com deal was found by Cheapflights users on 3/29. 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.
Sun 4/265:30 pm
ORD
- YQR
1 stop8h 40m
WestJet
Sun 5/38:35 am
YQR
- ORD
1 stop7h 05m
WestJet
Deal found 3/29![WestJet logo]()
$312
This Trip.com deal was found by Cheapflights users on 3/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:30 pm
ORD
- YQR
1 stop6h 50m
WestJet
Thu 5/218:35 am
YQR
- ORD
1 stop7h 05m
WestJet
Deal found 3/30![WestJet logo]()
$313
This Flightnetwork deal was found by Cheapflights users on 4/1. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/163:50 pm
ORD
- YXE
1 stop8h 26m
Air Canada
Fri 5/228:00 pm
YXE
- ORD
2 stops17h 53m
Air Canada
Deal found 4/1![Air Canada logo]()
$325
This Vliegwinkel deal was found by Cheapflights users on 4/1. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/169:55 am
ORD
- YXE
1 stop15h 40m
Multiple Airlines
Fri 5/227:00 am
YXE
- ORD
1 stop8h 40m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 5/1410:40 am
ORD
- YQR
2 stops10h 05m
Multiple Airlines
Thu 5/218:35 am
YQR
- ORD
1 stop7h 05m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Sun 4/265:50 am
ORD
- YXE
2 stops15h 30m
Multiple Airlines
Sun 5/38:50 am
YXE
- ORD
1 stop6h 50m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$358
This Air Canada deal was found by Cheapflights users on 4/1. 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.
Sat 6/203:45 pm
ORD
- YXE
1 stop8h 54m
Air Canada
Tue 6/236:00 am
YXE
- ORD
1 stop7h 55m
Air Canada
Deal found 4/1![Air Canada logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Thu 5/288:06 pm
ORD
- YQR
1 stop22h 14m
Multiple Airlines
Thu 6/410:45 am
YQR
- ORD
1 stop5h 39m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 3/30. 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.
Tue 6/26:00 am
ORD
- YQR
1 stop16h 30m
United Airlines
Fri 6/59:45 am
YQR
- ORD
1 stop12h 04m
United Airlines
Deal found 3/30![United Airlines logo]()
$383
This Air Canada deal was found by Cheapflights users on 4/1. 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 6/197:25 am
ORD
- YXE
1 stop12h 49m
Air Canada
Tue 6/236:00 am
YXE
- ORD
1 stop7h 55m
Air Canada
Deal found 4/1![Air Canada logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Wed 7/156:39 pm
ORD
- YXE
1 stop27h 56m
Multiple Airlines
Sat 7/257:00 am
YXE
- ORD
2 stops9h 39m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$394
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 April 3, 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 April 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 5/1410:40 am
ORD
- YQR
2 stops10h 05m
Multiple Airlines
Thu 5/218:35 am
YQR
- ORD
1 stop7h 05m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 3/29. 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.
Tue 6/26:00 am
ORD
- YQR
1 stop16h 30m
United Airlines
Fri 6/59:45 am
YQR
- ORD
1 stop12h 34m
United Airlines
Deal found 3/29![United Airlines logo]()
$383
This Air Canada deal was found by Cheapflights users on 4/2. 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 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 4/2![Air Canada logo]()
$409
This WestJet deal was found by Cheapflights users on 3/30. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:30 pm
ORD
- YQR
2 stops18h 45m
WestJet
Thu 5/218:20 pm
YQR
- ORD
2 stops19h 20m
WestJet
Deal found 3/30![WestJet logo]()
$452
This Delta deal was found by Cheapflights users on 3/31. 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 5/156:24 am
ORD
- YXE
2 stops7h 36m
Delta
Fri 5/226:00 am
YXE
- ORD
2 stops11h 05m
Delta
Deal found 3/31![Delta logo]()
$477
This Air Canada deal was found by Cheapflights users on 3/28. 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.
Tue 5/59:55 am
ORD
- YXE
1 stop14h 21m
Air Canada
Sat 5/98:00 pm
YXE
- ORD
1 stop12h 05m
Air Canada
Deal found 3/28![Air Canada logo]()
$410
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Fri 5/151:49 pm
ORD
- YXE
2 stops35h 46m
Multiple Airlines
Fri 5/227:00 am
YXE
- ORD
1 stop8h 40m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$429
This Air Canada deal was found by Cheapflights users on 4/2. 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.
Wed 5/138:35 pm
ORD
- YQR
1 stop13h 27m
Air Canada
Sun 5/175:45 am
YQR
- ORD
1 stop6h 40m
Air Canada
Deal found 4/2![Air Canada logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Thu 5/288:06 pm
ORD
- YQR
1 stop22h 14m
Multiple Airlines
Thu 6/46:00 am
YQR
- ORD
2 stops16h 01m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$431
This United Airlines deal was found by Cheapflights users on 4/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:05 am
ORD
- YQR
2 stops15h 25m
United Airlines
Sun 5/179:45 am
YQR
- ORD
1 stop14h 13m
United Airlines
Deal found 4/2![United Airlines logo]()
$489
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/261:35 pm
ORD
- YXE
2 stops12h 25m
Delta
Sat 10/36:00 am
YXE
- ORD
2 stops13h 24m
Delta
Deal found 4/2![Delta logo]()
$496
This Air Canada deal was found by Cheapflights users on 4/2. 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 6/188:40 pm
ORD
- YQR
1 stop13h 25m
Air Canada
Sun 6/215:45 am
YQR
- ORD
1 stop8h 10m
Air Canada
Deal found 4/2![Air Canada logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 4/2. 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.
Wed 6/34:05 pm
ORD
- YXE
2 stops21h 40m
Multiple Airlines
Wed 6/108:55 pm
YXE
- ORD
1 stop18h 45m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$437
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/261:00 pm
MDW
- YXE
2 stops11h 10m
Delta
Sat 10/37:00 am
YXE
- MDW
2 stops10h 31m
Delta
Deal found 4/2![Delta logo]()
$496
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1811:30 am
ORD
- YQR
2 stops12h 50m
Delta
Sun 6/2110:45 am
YQR
- ORD
1 stop5h 33m
Delta
Deal found 4/2![Delta logo]()
$496
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Tue 7/145:30 pm
ORD
- YXE
1 stop6h 40m
Multiple Airlines
Fri 7/248:55 pm
YXE
- ORD
2 stops19h 44m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$456
This Air Canada deal was found by Cheapflights users on 3/31. 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.
Fri 5/159:20 pm
ORD
- YXE
1 stop13h 26m
Air Canada
Fri 5/228:00 pm
YXE
- ORD
1 stop12h 50m
Air Canada
Deal found 3/31![Air Canada logo]()
$484
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Sun 4/266:00 am
MDW
- YXE
2 stops15h 20m
Multiple Airlines
Sun 5/311:35 am
YXE
- MDW
1 stop21h 10m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$456
This Delta deal was found by Cheapflights users on 4/1. 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 5/169:23 am
MDW
- YXE
2 stops12h 52m
Delta
Fri 5/227:00 am
YXE
- MDW
2 stops10h 33m
Delta
Deal found 4/1![Delta logo]()
$505
This Air Canada deal was found by Cheapflights users on 3/30. 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 6/39:55 am
ORD
- YXE
1 stop14h 21m
Air Canada
Fri 6/58:05 pm
YXE
- ORD
2 stops15h 06m
Air Canada
Deal found 3/30![Air Canada logo]()
$490
This Delta deal was found by Cheapflights users on 3/31. 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 5/159:23 am
MDW
- YXE
2 stops12h 52m
Delta
Fri 5/226:00 am
YXE
- MDW
2 stops11h 33m
Delta
Deal found 3/31![Delta logo]()
$506
This oojo deal was found by Cheapflights users on 3/30. 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.
Tue 7/149:49 am
MDW
- YXE
2 stops15h 46m
WestJet
Fri 7/246:00 am
YXE
- MDW
2 stops11h 25m
WestJet
Deal found 3/30![WestJet logo]()
$809
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Sat 5/1610:30 am
MDW
- YXE
1 stop15h 05m
Multiple Airlines
Fri 5/228:55 pm
YXE
- MDW
2 stops13h 09m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$568
This Mytrip deal was found by Cheapflights users on 4/2. 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.
Wed 6/37:13 pm
MDW
- YXE
2 stops30h 22m
Multiple Airlines
Wed 6/102:00 pm
YXE
- MDW
3 stops18h 40m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$636
This Delta deal was found by Cheapflights users on 4/1. 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 9/262:00 pm
MDW
- YXE
2 stops12h 00m
Delta
Sun 10/47:00 am
YXE
- MDW
2 stops10h 31m
Delta
Deal found 4/1![Delta logo]()
$755
This Delta deal was found by Cheapflights users on 3/30. 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
Fri 7/246:00 am
YXE
- MDW
2 stops11h 25m
Delta
Deal found 3/30![Delta logo]()
$835
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Wed 7/1510:25 am
MDW
- YXE
1 stop10h 50m
Multiple Airlines
Fri 7/241:20 pm
YXE
- MDW
1 stop19h 20m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$766
Last-minute flights from Chicago to SaskatchewanDiscover last-minute flight deals from Chicago to Saskatchewan. Data last updated April 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Saskatchewan. Data last updated April 3, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 4/1. 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.
Tue 4/212:35 pm
ORD
- YQR
1 stop7h 55m
United Airlines
Sat 4/259:45 am
YQR
- ORD
1 stop9h 29m
United Airlines
Deal found 4/1![United Airlines logo]()
$383
This Trip.com deal was found by Cheapflights users on 3/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:30 pm
ORD
- YXE
1 stop6h 40m
WestJet
Sun 5/38:50 am
YXE
- ORD
1 stop6h 50m
WestJet
Deal found 3/28![WestJet logo]()
$291
This Trip.com deal was found by Cheapflights users on 3/29. 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.
Sun 4/265:30 pm
ORD
- YQR
1 stop8h 40m
WestJet
Sun 5/38:35 am
YQR
- ORD
1 stop7h 05m
WestJet
Deal found 3/29![WestJet logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Sun 4/265:50 am
ORD
- YXE
2 stops15h 30m
Multiple Airlines
Sun 5/38:50 am
YXE
- ORD
1 stop6h 50m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$358
This Air Canada deal was found by Cheapflights users on 3/29. 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.
Tue 5/59:55 am
ORD
- YXE
1 stop14h 21m
Air Canada
Sat 5/98:00 pm
YXE
- ORD
1 stop12h 05m
Air Canada
Deal found 3/29![Air Canada logo]()
$410
This Trip.com deal was found by Cheapflights users on 3/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:30 pm
ORD
- YQR
1 stop6h 50m
WestJet
Thu 5/218:35 am
YQR
- ORD
1 stop7h 05m
WestJet
Deal found 3/30![WestJet logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 5/1410:40 am
ORD
- YQR
2 stops10h 05m
Multiple Airlines
Thu 5/218:35 am
YQR
- ORD
1 stop7h 05m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$357
This Flightnetwork deal was found by Cheapflights users on 4/1. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/163:50 pm
ORD
- YXE
1 stop8h 26m
Air Canada
Fri 5/228:00 pm
YXE
- ORD
2 stops17h 53m
Air Canada
Deal found 4/1![Air Canada logo]()
$325
This Vliegwinkel deal was found by Cheapflights users on 4/1. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/169:55 am
ORD
- YXE
1 stop15h 40m
Multiple Airlines
Fri 5/227:00 am
YXE
- ORD
1 stop8h 40m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Sat 5/169:37 pm
ORD
- YQR
2 stops20h 43m
Multiple Airlines
Sat 5/236:00 am
YQR
- ORD
1 stop9h 40m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$406
This Air Canada deal was found by Cheapflights users on 4/1. 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.
Sat 5/169:55 am
ORD
- YQR
1 stop10h 12m
Air Canada
Sat 5/235:45 am
YQR
- ORD
1 stop8h 10m
Air Canada
Deal found 4/1![Air Canada logo]()
$409
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Thu 5/288:06 pm
ORD
- YQR
1 stop22h 14m
Multiple Airlines
Thu 6/410:45 am
YQR
- ORD
1 stop5h 39m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$377
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 April 3, 2026.
Search for one-way flight options from Chicago to Saskatchewan. Find affordable one-way fares based on user searches. Data last updated April 3, 2026.
This Trip.com deal was found by Cheapflights users on 4/1. 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 4/305:30 pm
ORD
- YXE
1 stop8h 30m
WestJet
Deal found 4/1![WestJet logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 4/303:27 pm
MDW
- YXE
2 stops25h 13m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$170
This oojo deal was found by Cheapflights users on 3/28. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/242:20 pm
ORD
- YXE
1 stop21h 01m
WestJet
Deal found 3/28![WestJet logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 5/106:12 pm
ORD
- YQR
1 stop24h 08m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Thu 4/308:06 pm
ORD
- YXE
3 stops29h 54m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Fri 5/159:42 pm
ORD
- YQR
2 stops20h 38m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Fri 4/247:35 pm
ORD
- YXE
3 stops30h 13m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Fri 5/159:37 pm
ORD
- YXE
3 stops28h 23m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 3/30. 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 5/155:30 pm
ORD
- YQR
1 stop8h 40m
Delta
Deal found 3/30![Delta logo]()
$223
This Trip.com deal was found by Cheapflights users on 4/1. 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 4/309:29 am
MDW
- YXE
1 stop13h 06m
WestJet
Deal found 4/1![WestJet logo]()
$587
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 April 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $291 (Trip.com) |
One-way from | $146 (Trip.com) |
Popular in | December |
Cheapest in | September |
Average price | $313 |
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 April 3, 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
Quickest round-trip
ChicagoRegina
ORD - YQR
ORDYQR
Chicago O'Hare Intl
Thu 5/14
10:40 am-7:45 pm
2 stops10h 05m
Regina
Thu 5/21
8:35 am-4:40 pm
1 stop7h 05m
$357
ChicagoRegina
ORD - YQR
ORDYQR
Chicago O'Hare Intl
Tue 6/2
6:00 am-9:30 pm
1 stop16h 30m
Regina
Fri 6/5
9:45 am-11:19 pm
1 stop12h 34m
$383
ChicagoRegina
ORD - YQR
ORDYQR
Chicago O'Hare Intl
Fri 6/19
8:40 pm-9:05 am
1 stop13h 25m
Regina
Sun 6/21
5:45 am-2:55 pm
1 stop8h 10m
$409
ChicagoSaskatoon
ORD - YXE
ORDYXE
Chicago O'Hare Intl
Tue 5/5
9:55 am-11:16 pm
1 stop14h 21m
Saskatoon
Sat 5/9
8:00 pm-9:05 am
1 stop12h 05m
$410
ChicagoRegina
ORD - YQR
ORDYQR
Chicago O'Hare Intl
Wed 5/13
8:35 pm-9:02 am
1 stop13h 27m
Regina
Sun 5/17
5:45 am-1:25 pm
1 stop6h 40m
$416
ChicagoRegina
ORD - YQR
ORDYQR
Chicago O'Hare Intl
Thu 6/18
8:40 pm-9:05 am
1 stop13h 25m
Regina
Sun 6/21
5:45 am-2:55 pm
1 stop8h 10m
$416
ChicagoSaskatoon
ORD - YXE
ORDYXE
Chicago O'Hare Intl
Fri 5/15
1:49 pm-12:35 am
2 stops35h 46m
Saskatoon
Fri 5/22
7:00 am-4:40 pm
1 stop8h 40m
$429
ChicagoRegina
ORD - YQR
ORDYQR
Chicago O'Hare Intl
Thu 5/28
8:06 pm-5:20 pm
1 stop22h 14m
Regina
Thu 6/4
6:00 am-11:01 pm
2 stops16h 01m
$431
ChicagoSaskatoon
ORD - YXE
ORDYXE
Chicago O'Hare Intl
Wed 6/3
4:05 pm-12:45 pm
2 stops21h 40m
Saskatoon
Wed 6/10
8:55 pm-4:40 pm
1 stop18h 45m
$437
ChicagoRegina
ORD - YQR
ORDYQR
Chicago O'Hare Intl
Thu 5/14
5:30 pm-11:15 am
2 stops18h 45m
Regina
Thu 5/21
8:20 pm-4:40 pm
2 stops19h 20m
$452
Showing 1-10 of 38 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-YXE
MDW-YXE
ORD-YQR
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-YXE
MDW-YXE
ORD-YQR
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 April 3, 2026.
Get a feel of what it's like to fly with Delta and Air 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.
Food
7.2
Overall
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Overall
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Overall
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
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 April 3, 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 April 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$410 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$516 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$175 | Average$619 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$198 | Average$383 | FlexibilityNo cancel fee | On-time60% |