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Saskatchewan

$138+ 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 6/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
Mar 10 — Mar 171
Tue 3/10
Tue 3/17
1 adult, Economy
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Cheap flight deals from Chicago to Saskatchewan

Cheapest flights from Chicago to Saskatchewan
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 February 8, 2026.

This Trip.com deal was found by Cheapflights users on 2/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:30 pm
ORD
-
YXE
1 stop8h 25m
WestJet
Sun 5/178:50 am
YXE
-
ORD
1 stop6h 50m
WestJet
Deal found 2/6$219
This oojo deal was found by Cheapflights users on 2/7. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:30 pm
ORD
-
YQR
1 stop8h 40m
WestJet
Sat 5/307:00 am
YQR
-
ORD
1 stop8h 40m
WestJet
Deal found 2/7$239
This oojo deal was found by Cheapflights users on 2/7. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:30 pm
ORD
-
YXE
1 stop8h 25m
WestJet
Wed 5/208:50 am
YXE
-
ORD
1 stop6h 50m
WestJet
Deal found 2/7$245
This Trip.com deal was found by Cheapflights users on 2/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/215:30 pm
ORD
-
YXE
1 stop6h 40m
WestJet
Sun 5/247:00 am
YXE
-
ORD
1 stop8h 40m
WestJet
Deal found 2/7$295
This oojo deal was found by Cheapflights users on 2/6. 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.
Wed 6/245:30 pm
ORD
-
YQR
1 stop8h 37m
WestJet
Mon 6/2911:45 am
YQR
-
ORD
1 stop27h 58m
WestJet
Deal found 2/6$362
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 3/227:30 am
ORD
-
YQR
1 stop12h 01m
Multiple Airlines
Sun 3/298:45 pm
YQR
-
ORD
1 stop15h 50m
Multiple Airlines
Deal found 2/4$364
This United Airlines deal was found by Cheapflights users on 2/7. 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.
Tue 3/247:00 am
ORD
-
YQR
1 stop15h 51m
United Airlines
Tue 3/319:45 am
YQR
-
ORD
1 stop13h 45m
United Airlines
Deal found 2/7$369
This Trip.com deal was found by Cheapflights users on 2/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/302:20 pm
ORD
-
YXE
1 stop6h 38m
Multiple Airlines
Thu 4/97:10 am
YXE
-
ORD
1 stop9h 50m
Multiple Airlines
Deal found 2/6$381
This FlightHub deal was found by Cheapflights users on 2/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/195:30 pm
ORD
-
YQR
1 stop6h 50m
WestJet
Sun 6/219:00 pm
YQR
-
ORD
1 stop18h 43m
WestJet
Deal found 2/7$383
This Air Canada deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:45 am
ORD
-
YQR
2 stops11h 22m
Air Canada
Sat 5/305:45 am
YQR
-
ORD
2 stops13h 23m
Air Canada
Deal found 2/4$388
This Air Canada deal was found by Cheapflights users on 2/7. 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.
Mon 3/308:20 pm
ORD
-
YXE
1 stop13h 51m
Air Canada
Thu 4/95:00 am
YXE
-
ORD
1 stop7h 05m
Air Canada
Deal found 2/7$393
This Kiwi.com deal was found by Cheapflights users on 2/5. 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.
Sun 3/227:30 am
ORD
-
YXE
1 stop7h 07m
Multiple Airlines
Sun 3/293:45 pm
YXE
-
ORD
2 stops32h 14m
Multiple Airlines
Deal found 2/5$395

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 February 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$219
(Trip.com)

One-way from

$138
(Trip.com)
Provider with most accurate pricing for Chicago (CHI)-Saskatoon flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Saskatoon flights.
Search Deals
From Chicago (CHI) to Saskatchewan
Search Deals
One-way flight from Chicago (CHI) to Saskatchewan
Search Deals

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 February 8, 2026.
Use the filters below to find and compare flights from Chicago to Saskatchewan that are best for you.

Fly from

Chicago

Fly to

Saskatchewan

Route

Depart

Return

Price

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Fri 5/15

5:30 pm-12:55 am

1 stop8h 25m

Saskatoon

Sun 5/17

8:50 am-4:40 pm

1 stop6h 50m

$219

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 5/27

5:30 pm-1:10 am

1 stop8h 40m

Regina

Sat 5/30

7:00 am-4:40 pm

1 stop8h 40m

$239

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Thu 5/14

5:30 pm-12:55 am

1 stop8h 25m

Saskatoon

Wed 5/20

8:50 am-4:40 pm

1 stop6h 50m

$245

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Thu 5/28

5:30 pm-8:15 am

2 stops15h 45m

Saskatoon

Sun 5/31

7:00 am-4:40 pm

1 stop8h 40m

$265

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 6/24

5:30 pm-1:07 am

1 stop8h 37m

Regina

Mon 6/29

11:45 am-4:43 pm

1 stop27h 58m

$362

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 3/24

7:00 am-9:51 pm

1 stop15h 51m

Regina

Tue 3/31

9:45 am-12:30 am

1 stop13h 45m

$369

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Mon 3/30

2:20 pm-7:58 pm

1 stop6h 38m

Saskatoon

Thu 4/9

7:10 am-6:00 pm

1 stop9h 50m

$381

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

5:30 pm-11:20 pm

1 stop6h 50m

Regina

Sun 6/21

9:00 pm-4:43 pm

1 stop18h 43m

$383

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 5/27

8:45 am-7:07 pm

2 stops11h 22m

Regina

Sat 5/30

5:45 am-8:08 pm

2 stops13h 23m

$388

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Sun 3/22

7:30 am-1:37 pm

1 stop7h 07m

Saskatoon

Sun 3/29

3:45 pm-12:59 am

2 stops32h 14m

$395

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/5

Showing 1-10 of 38 results
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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.
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
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 February 8, 2026.
Get a feel of what it's like to fly with Delta 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.
Delta
7.9
Good
8,173 reviews

Comfort

7.9

Crew

8.5

Food

7.2

Overall

7.9

Entertainment

7.8

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,173 reviews
Delta
7.9
Good
8,173 reviews

Comfort

7.9

Crew

8.5

Food

7.2

Overall

7.9

Entertainment

7.8

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

  • How long is the flight from Chicago to Saskatchewan?

    Departing from Chicago to Saskatchewan will take you 8h 25m. There are 1124 mi between Chicago and Saskatchewan.

  • What are the most popular routes from Chicago to Saskatchewan?

    When deciding which route to take from Chicago to Saskatchewan consider Chicago O'Hare Intl - Regina, Chicago O'Hare Intl - Saskatoon or Chicago Midway - Saskatoon as they are the most popular.

  • Can I find deals for flights from Chicago to Saskatchewan that include hotel bookings?

    Yes. In addition to deals on Chicago to Saskatchewan flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Saskatchewan?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Saskatchewan.

  • Can I find deals for business class flights from Chicago to Saskatchewan?

    Yes. Cheapflights offers flight deals from Chicago to Saskatchewan by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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.
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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 February 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$184Average$466FlexibilityNo cancel feeOn-time69%
DeltaCheapest$188Average$467FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$198Average$383FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$245Average$649FlexibilityNo cancel feeOn-time67%

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