$260+ Cheap flights from Chicago (CHI) to Saskatchewan
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
Nov 19 — Nov 261
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Saskatchewan with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Saskatchewan
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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 October 20, 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 October 20, 2026.
This Booking.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/264:30 pm -
1 stop6h 57m
Wed 12/25:00 am -
1 stop8h 13m
Deal found 10/19![Air Canada logo]()
$536
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/127:35 pm -
2 stops25h 30m
Thu 11/1911:50 am -
1 stop6h 40m
Deal found 10/18![Multiple Airlines logo]()
$557
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/812:15 pm -
1 stop13h 05m
Thu 11/1911:50 am -
1 stop6h 40m
Deal found 10/18![Multiple Airlines logo]()
$564
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/127:35 pm -
1 stop23h 05m
Tue 11/1711:50 am -
2 stops36h 31m
Deal found 10/18![Multiple Airlines logo]()
$567
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/812:15 pm -
1 stop13h 05m
Tue 11/1711:50 am -
2 stops36h 31m
Deal found 10/18![Multiple Airlines logo]()
$572
This Kiwi.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/2510:00 am -
1 stop8h 40m
Sat 11/287:00 am -
1 stop10h 40m
Deal found 10/15![Multiple Airlines logo]()
$573
This Kiwi.com deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 12/1711:45 am -
1 stop6h 55m
Thu 1/146:45 am -
2 stops23h 25m
Deal found 10/17![Multiple Airlines logo]()
$587
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/276:20 pm -
2 stops26h 25m
Sun 12/67:00 am -
1 stop10h 40m
Deal found 10/18![Multiple Airlines logo]()
$593
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/97:50 pm -
2 stops19h 45m
Thu 11/1911:50 am -
1 stop6h 40m
Deal found 10/18![Multiple Airlines logo]()
$594
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/812:15 pm -
1 stop13h 05m
Mon 11/1611:50 am -
2 stops27h 41m
Deal found 10/18![Multiple Airlines logo]()
$602
This Air Canada deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 12/24:30 pm -
1 stop8h 01m
Wed 12/912:55 pm -
1 stop7h 03m
Deal found 10/18![Air Canada logo]()
$605
This Air Canada deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 12/254:30 pm -
1 stop8h 01m
Tue 1/512:55 pm -
1 stop7h 03m
Deal found 10/18![Air Canada logo]()
$622
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 October 20, 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 October 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/2510:00 am -
1 stop8h 40m
Sat 11/287:00 am -
1 stop10h 40m
Deal found 10/15![Multiple Airlines logo]()
$573
This United Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 11/182:30 pm -
1 stop8h 10m
Mon 11/2310:45 am -
1 stop12h 01m
Deal found 10/17![United Airlines logo]()
$633
This Air Canada deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 12/253:45 pm -
2 stops18h 56m
Tue 1/53:40 pm -
2 stops19h 27m
Deal found 10/18![Air Canada logo]()
$719
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:30 am -
2 stops13h 10m
Tue 11/247:00 am -
2 stops13h 17m
Deal found 10/16![Delta logo]()
$725
This Justfly.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 10/238:30 pm -
1 stop15h 10m
Fri 10/3011:55 am -
1 stop6h 35m
Deal found 10/19![Porter Airlines logo]()
$1,073
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 11/271:30 pm -
1 stop9h 10m
Tue 12/110:45 am -
1 stop8h 43m
Deal found 10/19![United Airlines logo]()
$633
This oojo deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:30 pm -
2 stops37h 05m
Sat 10/316:00 am -
2 stops10h 47m
Deal found 10/18![WestJet logo]()
$1,319
This Mytrip deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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.
Tue 12/16:21 am -
2 stops18h 59m
Tue 12/811:30 am -
3 stops27h 00m
Deal found 10/17![Multiple Airlines logo]()
$715
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/198:04 am -
2 stops10h 36m
Tue 11/247:00 am -
2 stops13h 17m
Deal found 10/18![Delta logo]()
$757
This Air Canada deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/208:40 pm -
1 stop14h 03m
Wed 11/255:00 am -
1 stop10h 38m
Deal found 10/16![Air Canada logo]()
$789
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/95:30 am -
2 stops13h 10m
Wed 11/185:35 am -
2 stops9h 20m
Deal found 10/18![Delta logo]()
$764
This Air Canada deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/198:45 am -
1 stop14h 42m
Wed 11/255:00 am -
2 stops14h 52m
Deal found 10/18![Air Canada logo]()
$793
This Air Canada deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 12/24:30 pm -
1 stop8h 01m
Wed 12/912:55 pm -
2 stops10h 34m
Deal found 10/18![Air Canada logo]()
$831
This Air Canada deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 10/284:30 pm -
1 stop8h 01m
Sat 10/314:00 am -
1 stop8h 13m
Deal found 10/15![Air Canada logo]()
$936
This Justfly.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 10/235:30 pm -
2 stops22h 15m
Fri 10/3011:55 am -
1 stop6h 35m
Deal found 10/19![Multiple Airlines logo]()
$1,240
This Justfly.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 10/238:29 am -
2 stops12h 46m
Fri 10/309:30 pm -
2 stops13h 43m
Deal found 10/19![WestJet logo]()
$1,814
Last-minute flights from Chicago to SaskatchewanDiscover last-minute flight deals from Chicago to Saskatchewan. Data last updated October 20, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Saskatchewan. Data last updated October 20, 2026 and is based on user searches.
This Justfly.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 10/238:30 pm -
1 stop15h 10m
Fri 10/3011:55 am -
1 stop6h 35m
Deal found 10/19![Porter Airlines logo]()
$1,073
This Air Canada deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 10/284:30 pm -
1 stop8h 01m
Sat 10/314:00 am -
1 stop8h 13m
Deal found 10/15![Air Canada logo]()
$936
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/812:15 pm -
1 stop13h 05m
Thu 11/1911:50 am -
1 stop6h 40m
Deal found 10/18![Multiple Airlines logo]()
$564
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/812:15 pm -
1 stop13h 05m
Tue 11/1711:50 am -
2 stops36h 31m
Deal found 10/18![Multiple Airlines logo]()
$572
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/812:15 pm -
1 stop13h 05m
Mon 11/1611:50 am -
2 stops27h 41m
Deal found 10/18![Multiple Airlines logo]()
$602
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/97:50 pm -
2 stops19h 45m
Thu 11/1911:50 am -
1 stop6h 40m
Deal found 10/18![Multiple Airlines logo]()
$594
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/127:35 pm -
2 stops25h 30m
Thu 11/1911:50 am -
1 stop6h 40m
Deal found 10/18![Multiple Airlines logo]()
$557
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/127:35 pm -
1 stop23h 05m
Tue 11/1711:50 am -
2 stops36h 31m
Deal found 10/18![Multiple Airlines logo]()
$567
This Kiwi.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/2510:00 am -
1 stop8h 40m
Sat 11/287:00 am -
1 stop10h 40m
Deal found 10/15![Multiple Airlines logo]()
$573
This Booking.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/264:30 pm -
1 stop6h 57m
Wed 12/25:00 am -
1 stop8h 13m
Deal found 10/19![Air Canada logo]()
$536
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/276:20 pm -
2 stops26h 25m
Sun 12/67:00 am -
1 stop10h 40m
Deal found 10/18![Multiple Airlines logo]()
$593
This Air Canada deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/274:30 pm -
1 stop8h 01m
Sun 12/612:55 pm -
1 stop7h 03m
Deal found 10/18![Air Canada logo]()
$633
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 October 20, 2026.
Search for one-way flight options from Chicago to Saskatchewan. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 12/310:37 pm -
2 stops20h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$260
This Air Canada deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/113:40 pm -
2 stops19h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Air Canada logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/186:30 am -
2 stops32h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/1912:15 pm -
1 stop13h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/1712:15 pm -
1 stop23h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Porter Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/206:20 pm -
2 stops30h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$304
This Air Canada deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/168:40 pm -
1 stop14h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Air Canada logo]()
$310
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 12/32:35 pm -
1 stop8h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![United Airlines logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/176:30 am -
3 stops33h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/216:40 am -
2 stops32h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$321
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 October 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $536 (Booking.com) |
One-way from | $260 (Kiwi.com) |
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 7,457,451 searches. Data last updated October 20, 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 Chicago O'Hare Intl - YQR Regina
ORDYQR
Chicago O'Hare Intl
Thu 12/3
10:37 pm-6:40 pm
2 stops20h 03m
Regina
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$260
ChicagoSaskatoon
ORD Chicago O'Hare Intl - YXE Saskatoon
ORDYXE
Chicago O'Hare Intl
Wed 11/11
3:40 pm-10:41 am
2 stops19h 01m
Saskatoon
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$268
ChicagoSaskatoon
ORD Chicago O'Hare Intl - YXE Saskatoon
ORDYXE
Chicago O'Hare Intl
Sat 11/21
12:15 pm-1:35 am
1 stop13h 20m
Saskatoon
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$280
ChicagoSaskatoon
ORD Chicago O'Hare Intl - YXE Saskatoon
ORDYXE
Chicago O'Hare Intl
Fri 11/20
6:20 pm-1:05 am
2 stops30h 45m
Saskatoon
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$304
ChicagoRegina
ORD Chicago O'Hare Intl - YQR Regina
ORDYQR
Chicago O'Hare Intl
Thu 12/3
2:35 pm-10:57 pm
1 stop8h 22m
Regina
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$312
ChicagoSaskatoon
ORD Chicago O'Hare Intl - YXE Saskatoon
ORDYXE
Chicago O'Hare Intl
Thu 11/19
5:30 am-3:10 pm
2 stops9h 40m
Saskatoon
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$330
Quickest round-trip
ChicagoSaskatoon
ORD Chicago O'Hare Intl - YXE Saskatoon
ORDYXE
Chicago O'Hare Intl
Wed 11/11
7:03 am-2:46 pm
1 stop7h 43m
Saskatoon
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$342
ChicagoRegina
ORD Chicago O'Hare Intl - YQR Regina
ORDYQR
Chicago O'Hare Intl
Wed 11/25
10:00 am-6:40 pm
1 stop8h 40m
Regina
Sat 11/28
7:00 am-5:40 pm
1 stop10h 40m
$573
ChicagoRegina
ORD Chicago O'Hare Intl - YQR Regina
ORDYQR
Chicago O'Hare Intl
Wed 11/18
2:30 pm-10:40 pm
1 stop8h 10m
Regina
Mon 11/23
10:45 am-10:46 pm
1 stop12h 01m
$633
ChicagoRegina
ORD Chicago O'Hare Intl - YQR Regina
ORDYQR
Chicago O'Hare Intl
Fri 11/27
1:30 pm-10:40 pm
1 stop9h 10m
Regina
Tue 12/1
10:45 am-7:28 pm
1 stop8h 43m
$633
Showing 1-10 of 23 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
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
No data available for this route at this time. Please check back soon.
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 October 20, 2026.
Get a feel of what it's like to fly with WestJet 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.
Crew
7.9
Food
6.2
Boarding
7.4
Entertainment
6.1
Comfort
7.1
Overall
7.2
Reviews
1 / 20
4.0
OkayJosh,Nov 2025
LAS - YEG
Crew
7.9
Food
6.2
Boarding
7.4
Entertainment
6.1
Comfort
7.1
Overall
7.2
Reviews
1 / 20
4.0
OkayJosh,Nov 2025
LAS - YEG
Crew
7.9
Food
6.2
Boarding
7.4
Entertainment
6.1
Comfort
7.1
Overall
7.2
Reviews
1 / 20
4.0
OkayJosh,Nov 2025
LAS - YEG
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 October 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Saskatchewan
Discover the top 2 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 7,457,451 searches. Data last updated October 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$213 | Average$642 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$377 | Average$614 | FlexibilityNo cancel fee | On-time67% |