$312+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
Dec 4 — Dec 111
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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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 November 4, 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 November 4, 2026.
This Air Canada deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/254:30 pm -
1 stop8h 01m
Tue 1/55:00 am -
1 stop10h 38m
Deal found 10/31![Air Canada logo]()
$509
This Air Canada deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/94:30 pm -
1 stop8h 01m
Sun 12/1312:55 pm -
1 stop7h 03m
Deal found 10/31![Air Canada logo]()
$527
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/273:56 pm -
1 stop6h 44m
Tue 12/110:45 am -
1 stop8h 43m
Deal found 10/31![United Airlines logo]()
$593
This Mytrip deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/148:30 am -
2 stops14h 55m
Mon 12/215:50 am -
2 stops13h 05m
Deal found 10/30![Multiple Airlines logo]()
$598
This Air Canada deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/274:30 pm -
1 stop6h 57m
Tue 12/15:00 am -
2 stops10h 02m
Deal found 10/30![Air Canada logo]()
$603
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:30 pm -
1 stop9h 10m
Tue 11/2410:45 am -
1 stop10h 45m
Deal found 10/31![United Airlines logo]()
$644
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:38 pm -
1 stop6h 02m
Mon 11/2311:50 am -
1 stop9h 43m
Deal found 11/2![Delta logo]()
$664
This Air Canada deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:21 pm -
1 stop13h 20m
Sat 11/285:00 am -
1 stop14h 05m
Deal found 11/1![Air Canada logo]()
$683
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 November 4, 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 November 4, 2026.
This Air Canada deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/254:30 pm -
1 stop8h 01m
Tue 1/55:00 am -
1 stop10h 38m
Deal found 10/31![Air Canada logo]()
$509
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/273:56 pm -
1 stop6h 44m
Tue 12/110:45 am -
1 stop8h 43m
Deal found 10/31![United Airlines logo]()
$593
This Mytrip deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/148:30 am -
2 stops14h 55m
Mon 12/215:50 am -
3 stops18h 36m
Deal found 10/30![Multiple Airlines logo]()
$604
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:38 pm -
1 stop6h 02m
Mon 11/2311:50 am -
1 stop9h 43m
Deal found 11/2![Delta logo]()
$664
This Air Canada deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/94:30 pm -
1 stop8h 01m
Sun 12/1312:55 pm -
1 stop7h 03m
Deal found 10/31![Air Canada logo]()
$527
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:51 am -
2 stops8h 49m
Tue 11/247:00 am -
2 stops13h 17m
Deal found 10/31![Delta logo]()
$717
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:30 pm -
1 stop9h 10m
Wed 11/2510:45 am -
2 stops20h 59m
Deal found 10/31![United Airlines logo]()
$731
This Air Canada deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:21 pm -
1 stop13h 20m
Sat 11/285:00 am -
1 stop14h 05m
Deal found 11/1![Air Canada logo]()
$683
Last-minute flights from Chicago to SaskatchewanDiscover last-minute flight deals from Chicago to Saskatchewan. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Saskatchewan. Data last updated November 4, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:30 pm -
1 stop9h 10m
Tue 11/2410:45 am -
1 stop10h 45m
Deal found 10/31![United Airlines logo]()
$644
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:38 pm -
1 stop6h 02m
Mon 11/2311:50 am -
1 stop9h 43m
Deal found 11/2![Delta logo]()
$664
This Air Canada deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:21 pm -
1 stop13h 20m
Sat 11/285:00 am -
1 stop14h 05m
Deal found 11/1![Air Canada logo]()
$683
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/273:56 pm -
1 stop6h 44m
Tue 12/110:45 am -
1 stop8h 43m
Deal found 10/31![United Airlines logo]()
$593
This Air Canada deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/274:30 pm -
1 stop6h 57m
Tue 12/15:00 am -
2 stops10h 02m
Deal found 10/30![Air Canada logo]()
$603
This Air Canada deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/94:30 pm -
1 stop8h 01m
Sun 12/1312:55 pm -
1 stop7h 03m
Deal found 10/31![Air Canada logo]()
$527
This Mytrip deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/148:30 am -
2 stops14h 55m
Mon 12/215:50 am -
2 stops13h 05m
Deal found 10/30![Multiple Airlines logo]()
$598
This Air Canada deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/254:30 pm -
1 stop8h 01m
Tue 1/55:00 am -
1 stop10h 38m
Deal found 10/31![Air Canada logo]()
$509
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 November 4, 2026.
Search for one-way flight options from Chicago to Saskatchewan. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/174:36 pm -
3 stops23h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$312
This Air Canada deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/118:45 am -
1 stop15h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Air Canada logo]()
$475
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/81:24 am -
3 stops23h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$484
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:55 am -
3 stops41h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$492
This oojo deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/1110:30 am -
2 stops14h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![WestJet logo]()
$590
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 November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $509 (Air Canada) |
One-way from | $312 (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 November 4, 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
Tue 11/17
4:36 pm-3:50 pm
3 stops23h 14m
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
Wed 11/11
8:45 am-12:31 am
1 stop15h 46m
Saskatoon
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$475
ChicagoRegina
ORD Chicago O'Hare Intl - YQR Regina
ORDYQR
Chicago O'Hare Intl
Sun 11/8
1:24 am-1:20 am
3 stops23h 56m
Regina
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$484
ChicagoRegina
ORD Chicago O'Hare Intl - YQR Regina
ORDYQR
Chicago O'Hare Intl
Sat 11/14
7:55 am-1:20 am
3 stops41h 25m
Regina
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$492
ChicagoSaskatoon
ORD Chicago O'Hare Intl - YXE Saskatoon
ORDYXE
Chicago O'Hare Intl
Fri 12/25
4:30 pm-12:31 am
1 stop8h 01m
Saskatoon
Tue 1/5
5:00 am-3:38 pm
1 stop10h 38m
$509
Quickest round-trip
ChicagoRegina
ORD Chicago O'Hare Intl - YQR Regina
ORDYQR
Chicago O'Hare Intl
Tue 11/17
10:15 am-11:27 pm
1 stop13h 12m
Regina
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$526
ChicagoSaskatoon
ORD Chicago O'Hare Intl - YXE Saskatoon
ORDYXE
Chicago O'Hare Intl
Wed 12/9
4:30 pm-12:31 am
1 stop8h 01m
Saskatoon
Sun 12/13
12:55 pm-7:58 pm
1 stop7h 03m
$527
ChicagoSaskatoon
ORD Chicago O'Hare Intl - YXE Saskatoon
ORDYXE
Chicago O'Hare Intl
Wed 11/11
10:30 am-1:05 am
2 stops14h 35m
Saskatoon
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$590
ChicagoRegina
ORD Chicago O'Hare Intl - YQR Regina
ORDYQR
Chicago O'Hare Intl
Fri 11/27
3:56 pm-10:40 pm
1 stop6h 44m
Regina
Tue 12/1
10:45 am-7:28 pm
1 stop8h 43m
$593
ChicagoSaskatoon
ORD Chicago O'Hare Intl - YXE Saskatoon
ORDYXE
Chicago O'Hare Intl
Mon 12/14
8:30 am-11:25 pm
2 stops14h 55m
Saskatoon
Mon 12/21
5:50 am-12:26 am
3 stops18h 36m
$604
Showing 1-10 of 14 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
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
ORD-YQR
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 November 4, 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.
Boarding
7.4
Overall
7.2
Comfort
7.1
Crew
7.9
Entertainment
6.1
Food
6.2
Reviews
1 / 20
4.0
OkayJosh,Nov 2025
LAS - YEG
Boarding
7.4
Overall
7.2
Comfort
7.1
Crew
7.9
Entertainment
6.1
Food
6.2
Reviews
1 / 20
4.0
OkayJosh,Nov 2025
LAS - YEG
Boarding
7.4
Overall
7.2
Comfort
7.1
Crew
7.9
Entertainment
6.1
Food
6.2
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 November 4, 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 November 4, 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% |