$144+ Cheap flights from Chicago (CHI) to Saskatchewan
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
Sep 29 — Oct 61
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 August 30, 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 August 30, 2026.
This Justfly.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/165:30 pm -
1 stop8h 30m
Mon 10/197:00 am -
1 stop8h 40m
Deal found 8/27![WestJet logo]()
$296
This Trip.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/115:30 pm -
1 stop8h 40m
Sun 10/187:00 am -
1 stop8h 40m
Deal found 8/27![WestJet logo]()
$297
This Trip.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/115:30 pm -
1 stop18h 05m
Sun 10/188:50 am -
1 stop6h 50m
Deal found 8/27![WestJet logo]()
$315
This Mytrip deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:30 pm -
1 stop8h 40m
Tue 9/225:45 am -
1 stop8h 10m
Deal found 8/28![Multiple Airlines logo]()
$343
This Mytrip deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Fri 10/95:30 pm -
1 stop6h 40m
Fri 10/167:50 pm -
1 stop12h 10m
Deal found 8/25![Multiple Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/215:30 pm -
1 stop8h 40m
Thu 9/2410:45 am -
1 stop24h 23m
Deal found 8/27![Multiple Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/243:20 pm -
1 stop10h 15m
Mon 9/284:30 pm -
2 stops17h 30m
Deal found 8/25![Multiple Airlines logo]()
$418
This Delta deal was found by Cheapflights users on 8/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1110:01 am -
2 stops12h 14m
Sun 10/186:00 am -
2 stops11h 00m
Deal found 8/28![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1612:27 pm -
2 stops11h 43m
Mon 10/197:00 am -
2 stops10h 00m
Deal found 8/29![Delta logo]()
$677
This Delta deal was found by Cheapflights users on 8/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/32:00 pm -
2 stops12h 00m
Thu 10/86:00 am -
2 stops11h 00m
Deal found 8/28![Delta logo]()
$679
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:27 pm -
2 stops10h 43m
Sun 10/257:30 am -
2 stops9h 30m
Deal found 8/29![Delta logo]()
$681
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 August 30, 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 August 30, 2026.
This FlightHub deal was found by Cheapflights users on 8/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:30 pm -
1 stop8h 30m
Mon 10/197:00 am -
1 stop8h 40m
Deal found 8/28![WestJet logo]()
$296
This Mytrip deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:30 pm -
1 stop8h 40m
Tue 9/225:45 am -
1 stop8h 10m
Deal found 8/28![Multiple Airlines logo]()
$343
This Air Canada deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:55 am -
1 stop9h 56m
Sun 10/46:00 am -
1 stop6h 23m
Deal found 8/25![Air Canada logo]()
$370
This United Airlines deal was found by Cheapflights users on 8/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:55 am -
1 stop16h 35m
Sun 9/209:45 am -
1 stop13h 14m
Deal found 8/28![United Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:55 pm -
2 stops10h 15m
Mon 10/197:00 am -
2 stops12h 30m
Deal found 8/27![Delta logo]()
$453
This Trip.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/115:30 pm -
1 stop8h 40m
Sun 10/188:35 am -
1 stop7h 05m
Deal found 8/27![WestJet logo]()
$299
This Air Canada deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:15 pm -
1 stop10h 01m
Mon 9/287:50 pm -
1 stop12h 10m
Deal found 8/25![Air Canada logo]()
$395
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/95:55 am -
1 stop16h 35m
Sat 9/129:45 am -
1 stop11h 14m
Deal found 8/26![United Airlines logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Mon 10/128:11 pm -
2 stops22h 09m
Mon 10/198:35 am -
1 stop7h 05m
Deal found 8/28![Multiple Airlines logo]()
$409
This Mytrip deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/115:30 pm -
2 stops15h 45m
Sun 10/183:30 pm -
2 stops24h 10m
Deal found 8/27![WestJet logo]()
$390
This Air Canada deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:35 pm -
1 stop6h 41m
Sun 11/15:00 am -
1 stop14h 58m
Deal found 8/26![Air Canada logo]()
$409
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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.
Sun 9/205:30 pm -
1 stop8h 30m
Thu 9/246:00 am -
2 stops11h 26m
Deal found 8/26![Delta logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/243:20 pm -
1 stop10h 15m
Mon 9/286:00 am -
1 stop28h 00m
Deal found 8/25![Multiple Airlines logo]()
$425
This Air Canada deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 10/238:40 pm -
1 stop13h 20m
Thu 10/294:00 am -
1 stop8h 13m
Deal found 8/25![Air Canada logo]()
$443
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1612:27 pm -
2 stops11h 43m
Mon 10/197:00 am -
2 stops10h 00m
Deal found 8/29![Delta logo]()
$677
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:27 pm -
2 stops10h 43m
Sun 10/257:30 am -
2 stops9h 30m
Deal found 8/29![Delta logo]()
$681
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Sun 10/115:31 pm -
1 stop5h 04m
Sun 10/186:00 am -
2 stops11h 00m
Deal found 8/27![Delta logo]()
$690
This oojo deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:29 am -
2 stops11h 46m
Mon 10/196:00 am -
2 stops33h 47m
Deal found 8/25![WestJet logo]()
$826
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/91:27 pm -
2 stops12h 33m
Fri 10/167:00 am -
2 stops10h 00m
Deal found 8/25![Delta logo]()
$870
Last-minute flights from Chicago to SaskatchewanDiscover last-minute flight deals from Chicago to Saskatchewan. Data last updated August 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Saskatchewan. Data last updated August 30, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:30 pm -
1 stop8h 40m
Tue 9/225:45 am -
1 stop8h 10m
Deal found 8/28![Multiple Airlines logo]()
$343
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/175:55 am -
1 stop16h 35m
Sun 9/209:45 am -
1 stop13h 14m
Deal found 8/27![United Airlines logo]()
$397
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:45 am -
2 stops11h 20m
Sun 9/205:45 am -
1 stop6h 38m
Deal found 8/27![Air Canada logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/215:30 pm -
1 stop8h 40m
Thu 9/2410:45 am -
1 stop24h 23m
Deal found 8/27![Multiple Airlines logo]()
$375
This Air Canada deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:15 pm -
1 stop10h 01m
Mon 9/287:50 pm -
1 stop12h 10m
Deal found 8/25![Air Canada logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/243:20 pm -
1 stop10h 15m
Mon 9/284:30 pm -
2 stops17h 30m
Deal found 8/25![Multiple Airlines logo]()
$418
This Justfly.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:30 pm -
1 stop8h 30m
Mon 9/2811:35 am -
1 stop7h 45m
Deal found 8/27![Multiple Airlines logo]()
$435
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/253:45 pm -
1 stop8h 31m
Mon 9/287:50 pm -
1 stop12h 10m
Deal found 8/27![Air Canada logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/255:30 pm -
1 stop6h 50m
Mon 9/2811:40 am -
2 stops16h 58m
Deal found 8/25![Multiple Airlines logo]()
$416
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/258:40 pm -
1 stop13h 20m
Sun 9/275:45 am -
1 stop6h 38m
Deal found 8/27![Air Canada logo]()
$434
This Air Canada deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:45 am -
2 stops11h 06m
Sun 10/46:00 am -
1 stop6h 23m
Deal found 8/25![Air Canada logo]()
$397
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:45 am -
2 stops11h 06m
Tue 9/297:55 pm -
1 stop12h 05m
Deal found 8/27![Air Canada logo]()
$409
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 August 30, 2026.
Search for one-way flight options from Chicago to Saskatchewan. Find affordable one-way fares based on user searches. Data last updated August 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/55:30 pm -
1 stop6h 40m
Deal found 8/26![WestJet logo]()
$144
This FlightHub deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Sun 10/115:30 pm -
1 stop6h 40m
Deal found 8/27![WestJet logo]()
$146
This Air Canada deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 11/114:30 pm -
1 stop8h 01m
Deal found 8/27![Air Canada logo]()
$149
This FlightHub deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Fri 9/255:30 pm -
1 stop6h 50m
Deal found 8/27![WestJet logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/45:30 pm -
1 stop8h 30m
Deal found 8/26![WestJet logo]()
$150
This Flightnetwork deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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.
Fri 10/235:30 pm -
1 stop6h 50m
Deal found 8/26![WestJet logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/105:30 pm -
2 stops15h 45m
Deal found 8/25![WestJet logo]()
$173
This Air Canada deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:35 pm -
1 stop6h 41m
Deal found 8/26![Air Canada logo]()
$175
This Air Canada deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:15 pm -
1 stop10h 01m
Deal found 8/25![Air Canada logo]()
$178
This Goibibo deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Goibibo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1111:05 am -
2 stops13h 11m
Deal found 8/27![Air Canada logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/257:28 pm -
3 stops25h 17m
Deal found 8/27![Multiple Airlines logo]()
$195
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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.
Sun 10/111:27 pm -
2 stops10h 43m
Deal found 8/27![Delta logo]()
$204
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 August 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $296 (Justfly.com) |
One-way from | $144 (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 August 30, 2026.
Use the filters below to find and compare flights from Chicago to Saskatchewan that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSaskatoon
ORD Chicago O'Hare Intl - YXE Saskatoon
ORDYXE
Chicago O'Hare Intl
Fri 10/16
5:30 pm-1:00 am
1 stop8h 30m
Saskatoon
Mon 10/19
7:00 am-4:40 pm
1 stop8h 40m
$296
Quickest round-trip
ChicagoRegina
ORD Chicago O'Hare Intl - YQR Regina
ORDYQR
Chicago O'Hare Intl
Sun 10/11
5:30 pm-1:10 am
1 stop8h 40m
Regina
Sun 10/18
8:35 am-4:40 pm
1 stop7h 05m
$299
ChicagoRegina
ORD Chicago O'Hare Intl - YQR Regina
ORDYQR
Chicago O'Hare Intl
Tue 9/15
5:30 pm-1:10 am
1 stop8h 40m
Regina
Tue 9/22
5:45 am-2:55 pm
1 stop8h 10m
$343
ChicagoSaskatoon
ORD Chicago O'Hare Intl - YXE Saskatoon
ORDYXE
Chicago O'Hare Intl
Sat 9/26
9:55 am-6:51 pm
1 stop9h 56m
Saskatoon
Sun 10/4
6:00 am-1:23 pm
1 stop6h 23m
$370
ChicagoSaskatoon
ORD Chicago O'Hare Intl - YXE Saskatoon
ORDYXE
Chicago O'Hare Intl
Sun 10/11
5:30 pm-8:15 am
2 stops15h 45m
Saskatoon
Sun 10/18
3:30 pm-4:40 pm
2 stops24h 10m
$390
ChicagoSaskatoon
ORD Chicago O'Hare Intl - YXE Saskatoon
ORDYXE
Chicago O'Hare Intl
Thu 9/24
2:15 pm-11:16 pm
1 stop10h 01m
Saskatoon
Mon 9/28
7:50 pm-9:00 am
1 stop12h 10m
$395
ChicagoRegina
ORD Chicago O'Hare Intl - YQR Regina
ORDYQR
Chicago O'Hare Intl
Thu 9/17
5:55 am-9:30 pm
1 stop16h 35m
Regina
Sun 9/20
9:45 am-11:59 pm
1 stop13h 14m
$397
ChicagoRegina
ORD Chicago O'Hare Intl - YQR Regina
ORDYQR
Chicago O'Hare Intl
Wed 9/9
5:55 am-9:30 pm
1 stop16h 35m
Regina
Sat 9/12
9:45 am-9:59 pm
1 stop11h 14m
$397
ChicagoRegina
ORD Chicago O'Hare Intl - YQR Regina
ORDYQR
Chicago O'Hare Intl
Mon 10/12
8:11 pm-5:20 pm
2 stops22h 09m
Regina
Mon 10/19
8:35 am-4:40 pm
1 stop7h 05m
$409
ChicagoSaskatoon
ORD Chicago O'Hare Intl - YXE Saskatoon
ORDYXE
Chicago O'Hare Intl
Sat 10/17
5:35 pm-11:16 pm
1 stop6h 41m
Saskatoon
Sun 11/1
5:00 am-7:58 pm
1 stop14h 58m
$409
Showing 1-10 of 35 resultsSorted by cheapest first
Best time to book a flight from Chicago to Saskatchewan
Have a flexible travel schedule? Discover the best time to fly to Saskatchewan from Chicago with our price prediction graph.
ORD-YQR
ORD-YXE
MDW-YXE
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Saskatchewan
CHI-CASK
ORD-YQR
ORD-YXE
MDW-YXE
How much does it cost to fly round-trip from Chicago to Saskatchewan?
Airfare is typical for this route at the moment.
Chicago to Saskatchewan flights typically cost between $217 and $643 in October.The cheapest round-trip price found within the last 5 days was $296 on WestJet (Oct 16-Oct 19).
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 August 30, 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.
Overall
7.2
Boarding
7.4
Entertainment
6.1
Comfort
7.1
Food
6.2
Crew
7.9
Reviews
1 / 20
4.0
OkayJosh,Nov 2025
LAS - YEG
Overall
7.2
Boarding
7.4
Entertainment
6.1
Comfort
7.1
Food
6.2
Crew
7.9
Reviews
1 / 20
4.0
OkayJosh,Nov 2025
LAS - YEG
Overall
7.2
Boarding
7.4
Entertainment
6.1
Comfort
7.1
Food
6.2
Crew
7.9
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 August 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Chicago to Saskatchewan
Discover the top 3 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 August 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$609 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$175 | Average$614 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$213 | Average$687 | FlexibilityNo cancel fee | On-time69% |