$166+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
may. 10 — may. 171
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 abril 10, 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 abril 10, 2026.
This Trip.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
dom. 5/245:30 pm
ORD
- YXE
1 stop8h 30m
Multiple Airlines
dom. 5/316:00 am
YXE
- ORD
1 stop7h 55m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$333
This Trip.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
vie. 6/125:30 pm
ORD
- YXE
1 stop6h 40m
Multiple Airlines
mar. 6/168:05 pm
YXE
- ORD
1 stop11h 55m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 7/195:30 pm
ORD
- YXE
1 stop8h 30m
WestJet
vie. 7/248:50 am
YXE
- ORD
1 stop6h 50m
WestJet
Deal found 4/5![WestJet logo]()
$380
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/133:00 pm
ORD
- YQR
1 stop7h 30m
United Airlines
dom. 5/179:45 am
YQR
- ORD
1 stop14h 13m
United Airlines
Deal found 4/5![United Airlines logo]()
$390
This Trip.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
sáb. 6/138:20 pm
ORD
- YXE
1 stop14h 26m
Air Canada
mar. 6/168:05 pm
YXE
- ORD
1 stop11h 55m
Air Canada
Deal found 4/9![Air Canada logo]()
$394
This Air Canada deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/203:45 pm
ORD
- YXE
1 stop8h 54m
Air Canada
jue. 6/258:05 pm
YXE
- ORD
1 stop16h 05m
Air Canada
Deal found 4/7![Air Canada logo]()
$397
This Gotogate deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/205:30 pm
ORD
- YXE
1 stop8h 30m
WestJet
sáb. 9/262:00 pm
YXE
- ORD
1 stop25h 40m
WestJet
Deal found 4/6![WestJet logo]()
$409
This Air Canada deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/69:55 am
ORD
- YQR
1 stop10h 12m
Air Canada
sáb. 5/95:45 am
YQR
- ORD
1 stop8h 10m
Air Canada
Deal found 4/5![Air Canada logo]()
$416
This Air Canada deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/263:45 pm
ORD
- YXE
1 stop8h 31m
Air Canada
dom. 10/46:00 am
YXE
- ORD
1 stop6h 23m
Air Canada
Deal found 4/6![Air Canada logo]()
$418
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/209:37 pm
ORD
- YQR
2 stops20h 43m
Multiple Airlines
mié. 5/278:35 am
YQR
- ORD
1 stop7h 05m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$418
This oojo deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/245:30 pm
ORD
- YXE
1 stop6h 40m
WestJet
vie. 8/288:50 am
YXE
- ORD
1 stop6h 50m
WestJet
Deal found 4/6![WestJet logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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.
lun. 6/226:31 pm
ORD
- YQR
1 stop23h 49m
Multiple Airlines
lun. 6/2910:45 am
YQR
- ORD
1 stop5h 39m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$423
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 abril 10, 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 abril 10, 2026.
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/133:00 pm
ORD
- YQR
1 stop7h 30m
United Airlines
dom. 5/179:45 am
YQR
- ORD
1 stop14h 13m
United Airlines
Deal found 4/5![United Airlines logo]()
$390
This Flightnetwork deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
sáb. 6/139:55 am
ORD
- YXE
1 stop14h 21m
Air Canada
mar. 6/168:05 pm
YXE
- ORD
2 stops13h 13m
Air Canada
Deal found 4/9![Air Canada logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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.
lun. 6/226:31 pm
ORD
- YQR
1 stop23h 49m
Multiple Airlines
lun. 6/2910:45 am
YQR
- ORD
1 stop5h 39m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$423
This FlightHub deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/205:30 pm
ORD
- YXE
2 stops15h 45m
WestJet
sáb. 9/263:30 pm
YXE
- ORD
2 stops24h 10m
WestJet
Deal found 4/6![WestJet logo]()
$446
This Delta deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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.
mié. 10/711:30 am
ORD
- YXE
2 stops14h 30m
Delta
dom. 10/117:00 am
YXE
- ORD
1 stop8h 40m
Delta
Deal found 4/8![Delta logo]()
$481
This Mytrip deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
dom. 5/245:30 pm
ORD
- YXE
1 stop8h 30m
Multiple Airlines
dom. 5/3111:25 am
YXE
- ORD
3 stops30h 41m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$431
This United Airlines deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
sáb. 5/236:00 am
ORD
- YQR
1 stop16h 30m
United Airlines
sáb. 5/309:45 am
YQR
- ORD
1 stop9h 20m
United Airlines
Deal found 4/9![United Airlines logo]()
$433
This Air Canada deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/309:55 am
ORD
- YQR
1 stop10h 12m
Air Canada
mié. 6/35:45 am
YQR
- ORD
1 stop6h 40m
Air Canada
Deal found 4/7![Air Canada logo]()
$437
This Delta deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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.
sáb. 9/261:35 pm
ORD
- YXE
2 stops12h 25m
Delta
dom. 10/46:00 am
YXE
- ORD
2 stops13h 24m
Delta
Deal found 4/8![Delta logo]()
$496
This Air Canada deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/268:45 am
ORD
- YXE
2 stops15h 31m
Air Canada
dom. 10/46:00 am
YXE
- ORD
1 stop6h 23m
Air Canada
Deal found 4/6![Air Canada logo]()
$451
This United Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/203:45 pm
ORD
- YXE
1 stop8h 54m
United Airlines
jue. 6/258:05 pm
YXE
- ORD
1 stop16h 05m
United Airlines
Deal found 4/7![United Airlines logo]()
$472
This Delta deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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.
sáb. 9/261:00 pm
MDW
- YXE
2 stops13h 00m
Delta
dom. 10/47:00 am
YXE
- MDW
2 stops10h 31m
Delta
Deal found 4/8![Delta logo]()
$496
This Air Canada deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
vie. 6/198:40 pm
ORD
- YQR
1 stop13h 25m
Air Canada
dom. 6/215:45 am
YQR
- ORD
1 stop8h 10m
Air Canada
Deal found 4/9![Air Canada logo]()
$459
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/189:48 pm
ORD
- YQR
2 stops20h 32m
Multiple Airlines
dom. 6/2110:45 am
YQR
- ORD
1 stop7h 24m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$518
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/67:05 am
ORD
- YQR
2 stops15h 25m
United Airlines
sáb. 5/99:45 am
YQR
- ORD
1 stop14h 13m
United Airlines
Deal found 4/5![United Airlines logo]()
$489
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/219:23 am
MDW
- YXE
2 stops12h 52m
Delta
jue. 5/286:00 am
YXE
- MDW
2 stops11h 33m
Delta
Deal found 4/6![Delta logo]()
$505
This Air Canada deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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.
mié. 7/155:35 pm
ORD
- YXE
1 stop7h 04m
Air Canada
mié. 7/226:00 am
YXE
- ORD
1 stop7h 55m
Air Canada
Deal found 4/8![Air Canada logo]()
$476
This United Airlines deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
mar. 6/912:55 pm
ORD
- YXE
1 stop11h 21m
United Airlines
mié. 6/106:00 am
YXE
- ORD
1 stop6h 25m
United Airlines
Deal found 4/9![United Airlines logo]()
$503
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/67:10 am
ORD
- YQR
2 stops11h 10m
Delta
sáb. 5/910:45 am
YQR
- ORD
2 stops12h 14m
Delta
Deal found 4/5![Delta logo]()
$506
This Delta deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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.
sáb. 5/2311:09 am
ORD
- YQR
2 stops13h 11m
Delta
sáb. 5/306:00 am
YQR
- ORD
2 stops13h 14m
Delta
Deal found 4/8![Delta logo]()
$512
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
dom. 5/241:22 pm
MDW
- YXE
2 stops12h 38m
Delta
dom. 5/317:00 am
YXE
- MDW
2 stops10h 33m
Delta
Deal found 4/9![Delta logo]()
$530
This Mytrip deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
dom. 5/249:23 am
MDW
- YXE
3 stops26h 15m
Multiple Airlines
dom. 5/316:00 am
YXE
- MDW
3 stops11h 33m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$767
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 7/199:20 am
MDW
- YXE
2 stops13h 15m
Delta
sáb. 7/257:00 am
YXE
- MDW
2 stops9h 52m
Delta
Deal found 4/5![Delta logo]()
$781
This Delta deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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.
lun. 5/251:22 pm
MDW
- YXE
2 stops10h 48m
Delta
lun. 6/16:00 am
YXE
- MDW
2 stops11h 33m
Delta
Deal found 4/10![Delta logo]()
$792
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/241:00 pm
MDW
- YXE
2 stops13h 00m
Delta
vie. 8/286:00 am
YXE
- MDW
2 stops11h 31m
Delta
Deal found 4/6![Delta logo]()
$796
Last-minute flights from Chicago to SaskatchewanDiscover last-minute flight deals from Chicago to Saskatchewan. Data last updated abril 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Saskatchewan. Data last updated abril 10, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/69:55 am
ORD
- YQR
1 stop10h 12m
Air Canada
sáb. 5/95:45 am
YQR
- ORD
1 stop8h 10m
Air Canada
Deal found 4/5![Air Canada logo]()
$416
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/67:05 am
ORD
- YQR
2 stops15h 25m
United Airlines
sáb. 5/99:45 am
YQR
- ORD
1 stop14h 13m
United Airlines
Deal found 4/5![United Airlines logo]()
$489
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/67:10 am
ORD
- YQR
2 stops11h 10m
Delta
sáb. 5/910:45 am
YQR
- ORD
2 stops12h 14m
Delta
Deal found 4/5![Delta logo]()
$506
This Air Canada deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/79:55 am
ORD
- YXE
1 stop9h 56m
Air Canada
mié. 5/138:00 pm
YXE
- ORD
1 stop12h 00m
Air Canada
Deal found 4/7![Air Canada logo]()
$430
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/133:00 pm
ORD
- YQR
1 stop7h 30m
United Airlines
dom. 5/179:45 am
YQR
- ORD
1 stop14h 13m
United Airlines
Deal found 4/5![United Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/209:37 pm
ORD
- YQR
2 stops20h 43m
Multiple Airlines
mié. 5/278:35 am
YQR
- ORD
1 stop7h 05m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$418
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/211:49 pm
ORD
- YXE
2 stops35h 46m
Multiple Airlines
jue. 5/288:55 pm
YXE
- ORD
1 stop18h 45m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$487
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/219:23 am
MDW
- YXE
2 stops12h 52m
Delta
jue. 5/286:00 am
YXE
- MDW
2 stops11h 33m
Delta
Deal found 4/6![Delta logo]()
$505
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
sáb. 5/239:17 am
ORD
- YQR
2 stops33h 03m
Multiple Airlines
sáb. 5/307:00 am
YQR
- ORD
1 stop8h 40m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$428
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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.
sáb. 5/236:00 am
ORD
- YQR
1 stop16h 30m
United Airlines
sáb. 5/309:45 am
YQR
- ORD
1 stop9h 20m
United Airlines
Deal found 4/8![United Airlines logo]()
$433
This Trip.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
dom. 5/245:30 pm
ORD
- YXE
1 stop8h 30m
Multiple Airlines
dom. 5/316:00 am
YXE
- ORD
1 stop7h 55m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$333
This Air Canada deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/309:55 am
ORD
- YQR
1 stop10h 12m
Air Canada
mié. 6/35:45 am
YQR
- ORD
1 stop6h 40m
Air Canada
Deal found 4/7![Air Canada logo]()
$437
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 abril 10, 2026.
Search for one-way flight options from Chicago to Saskatchewan. Find affordable one-way fares based on user searches. Data last updated abril 10, 2026.
This oojo deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
mar. 9/155:30 pm
ORD
- YXE
1 stop6h 40m
WestJet
Deal found 4/9![WestJet logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/59:37 pm
ORD
- YXE
2 stops21h 28m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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.
jue. 7/306:31 pm
ORD
- YXE
2 stops26h 49m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$193
This Air Canada deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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.
jue. 7/305:35 pm
ORD
- YXE
1 stop7h 04m
Air Canada
Deal found 4/10![Air Canada logo]()
$219
This American Airlines deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/258:08 am
ORD
- YXE
1 stop8h 20m
American Airlines
Deal found 4/10![American Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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.
lun. 5/252:00 pm
ORD
- YXE
2 stops10h 10m
Delta
Deal found 4/10![Delta logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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.
lun. 5/259:37 pm
ORD
- YXE
3 stops52h 23m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$274
This Air Canada deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/53:50 pm
ORD
- YXE
1 stop8h 26m
Air Canada
Deal found 4/5![Air Canada logo]()
$282
This oojo deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/59:27 am
MDW
- YXE
2 stops16h 08m
WestJet
Deal found 4/5![WestJet logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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.
jue. 7/305:30 pm
ORD
- YXE
3 stops22h 15m
WestJet
Deal found 4/10![WestJet logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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.
lun. 5/256:23 am
MDW
- YXE
3 stops31h 37m
WestJet
Deal found 4/10![WestJet logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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.
mar. 9/156:01 am
ORD
- YXE
3 stops15h 19m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$371
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 abril 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $333 (Trip.com) |
One-way from | $189 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $422 |
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 abril 10, 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
ChicagoRegina
ORD - YQR
ORDYQR
Chicago O'Hare Intl
mié. 5/13
3:00 pm-9:30 pm
1 stop7h 30m
Regina
dom. 5/17
9:45 am-12:58 am
1 stop14h 13m
$390
ChicagoSaskatoon
ORD - YXE
ORDYXE
Chicago O'Hare Intl
sáb. 6/13
9:55 am-11:16 pm
1 stop14h 21m
Saskatoon
mar. 6/16
8:05 pm-10:18 am
2 stops13h 13m
$403
ChicagoRegina
ORD - YQR
ORDYQR
Chicago O'Hare Intl
lun. 6/22
6:31 pm-5:20 pm
1 stop23h 49m
Regina
lun. 6/29
10:45 am-5:24 pm
1 stop5h 39m
$423
ChicagoSaskatoon
ORD - YXE
ORDYXE
Chicago O'Hare Intl
dom. 5/24
5:30 pm-1:00 am
1 stop8h 30m
Saskatoon
dom. 5/31
11:25 am-7:06 pm
3 stops30h 41m
$431
ChicagoRegina
ORD - YQR
ORDYQR
Chicago O'Hare Intl
sáb. 5/23
6:00 am-9:30 pm
1 stop16h 30m
Regina
sáb. 5/30
9:45 am-8:05 pm
1 stop9h 20m
$433
ChicagoRegina
ORD - YQR
ORDYQR
Chicago O'Hare Intl
sáb. 5/30
9:55 am-7:07 pm
1 stop10h 12m
Regina
mié. 6/3
5:45 am-1:25 pm
1 stop6h 40m
$437
ChicagoSaskatoon
ORD - YXE
ORDYXE
Chicago O'Hare Intl
dom. 9/20
5:30 pm-8:15 am
2 stops15h 45m
Saskatoon
sáb. 9/26
3:30 pm-4:40 pm
2 stops24h 10m
$446
ChicagoSaskatoon
ORD - YXE
ORDYXE
Chicago O'Hare Intl
sáb. 9/26
8:45 am-11:16 pm
2 stops15h 31m
Saskatoon
dom. 10/4
6:00 am-1:23 pm
1 stop6h 23m
$451
ChicagoRegina
ORD - YQR
ORDYQR
Chicago O'Hare Intl
vie. 6/19
8:40 pm-9:05 am
1 stop13h 25m
Regina
dom. 6/21
5:45 am-2:55 pm
1 stop8h 10m
$459
ChicagoSaskatoon
ORD - YXE
ORDYXE
Chicago O'Hare Intl
sáb. 6/20
3:45 pm-11:39 pm
1 stop8h 54m
Saskatoon
jue. 6/25
8:05 pm-1:10 pm
1 stop16h 05m
$472
Showing 1-10 of 37 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 abril 10, 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.
Overall
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Crew
8.5
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 abril 10, 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 abril 10, 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% |