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Saskatchewan

$94+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
Jan 21 — Jan 281
Wed 1/21
Wed 1/28
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 December 22, 2025.

This United Airlines deal was found by Cheapflights users on 12/19. 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.
Sun 12/213:55 pmORD - YXE
1 stop7h 40mUnited Airlines
Sat 1/1012:40 pmYXE - ORD
2 stops24h 28mUnited Airlines
Deal found 12/19$986
This Air Canada deal was found by Cheapflights users on 12/20. 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 12/279:20 pmORD - YXE
1 stop13h 15mAir Canada
Mon 1/511:25 amYXE - ORD
1 stop8h 15mAir Canada
Deal found 12/20$988
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/2310:22 pmORD - YXE
2 stops40h 16mMultiple Airlines
Thu 1/89:45 pmYXE - ORD
1 stop15h 50mMultiple Airlines
Deal found 12/21$994
This Delta deal was found by Cheapflights users on 12/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:35 amORD - YXE
1 stop8h 03mDelta
Sat 1/177:00 amYXE - ORD
2 stops14h 05mDelta
Deal found 12/19$1,009
This Air Canada deal was found by Cheapflights users on 12/21. 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 12/273:55 pmORD - YXE
1 stop7h 40mMultiple Airlines
Mon 1/53:25 pmYXE - ORD
1 stop18h 40mMultiple Airlines
Deal found 12/21$1,021
This Air Canada deal was found by Cheapflights users on 12/20. 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 12/278:30 pmORD - YXE
1 stop14h 05mAir Canada
Tue 12/3011:30 amYXE - ORD
1 stop8h 15mAir Canada
Deal found 12/20$1,029
This Air Canada deal was found by Cheapflights users on 12/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/213:55 pmORD - YXE
1 stop7h 40mAir Canada
Sat 1/106:00 amYXE - ORD
1 stop9h 10mAir Canada
Deal found 12/19$1,043
This FlightHub deal was found by Cheapflights users on 12/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/277:05 pmORD - YXE
2 stops23h 57mWestJet
Mon 1/54:30 pmYXE - ORD
2 stops29h 13mWestJet
Deal found 12/19$1,051
This FlightHub deal was found by Cheapflights users on 12/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2711:48 amMDW - YXE
2 stops31h 14mWestJet
Mon 1/54:30 pmYXE - MDW
2 stops26h 02mWestJet
Deal found 12/19$1,051

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 December 22, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$212
(WestJet)

One-way from

$94
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$706
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
Highest demand for flights based on searches. 20% potential increase in price ($124 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 22, 2025.
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

Sun 5/24

5:30 pm-12:53 am

1 stop8h 23m

Saskatoon

Sat 5/30

7:00 am-4:43 pm

1 stop8h 43m

$141

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Mon 5/11

5:30 pm-3:11 pm

2 stops22h 41m

Saskatoon

Fri 5/15

7:55 am-4:43 pm

1 stop7h 48m

$181

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Fri 5/1

5:30 pm-6:03 pm

1 stop25h 33m

Saskatoon

Sun 5/3

7:00 am-4:43 pm

1 stop8h 43m

$212

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Fri 1/9

2:20 pm-8:59 pm

1 stop6h 39m

Saskatoon

Fri 1/16

11:55 am-4:52 pm

2 stops28h 57m

$226

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Fri 5/22

5:30 pm-6:03 pm

1 stop25h 33m

Saskatoon

Mon 5/25

7:00 am-4:43 pm

1 stop8h 43m

$284

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 3/6

2:20 pm-12:18 am

1 stop9h 58m

Regina

Sun 3/8

7:20 pm-1:35 pm

1 stop17h 15m

$297

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Tue 4/7

5:57 pm-9:26 am

1 stop16h 29m

Saskatoon

Wed 4/8

2:30 pm-8:03 am

1 stop16h 33m

$321

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 1/23

8:45 pm-10:39 am

1 stop13h 54m

Regina

Sun 1/25

5:00 am-7:45 pm

1 stop14h 45m

$332

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 2/3

12:53 pm-10:51 pm

1 stop9h 58m

Regina

Tue 2/10

10:45 am-9:15 pm

1 stop10h 30m

$336

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 2/5

2:00 pm-11:19 pm

1 stop9h 19m

Regina

Thu 2/12

6:10 pm-1:35 pm

2 stops19h 25m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

Showing 1-10 of 27 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

What is the cheapest month to book a flight from Chicago to Saskatchewan?

Currently, November is the cheapest month in which you can book a flight from Chicago to Saskatchewan (average of $118). Flying from Chicago to Saskatchewan in March is currently the most expensive (average of $742). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to SK?

Find hourly flight availability from Chicago to Saskatchewan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 22, 2025.

One of the essential ways to save on airfare from Chicago to Saskatchewan is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 47% on airfare.

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 December 22, 2025.
Get a feel of what it's like to fly with Delta and WestJet 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
8,014 reviews

Overall

7.9

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

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
8,014 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

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.
WestJet
7.2
Good
3,209 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

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 23m. There are 1124 mi between Chicago and Saskatchewan. This flight may include one or multiple stops.

  • 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 - Saskatoon, Chicago O'Hare Intl - Regina 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.

  • What is the cheapest month to book a flight from Chicago to Saskatchewan?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Saskatchewan (average of $118). Flying from Chicago to Saskatchewan in March is currently the most expensive (average of $742). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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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 December 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$188Average$475FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$245Average$661FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$284Average$466FlexibilityNo cancel feeOn-time69%
WestJetCheapest$289Average$385FlexibilityNo cancel feeOn-time60%

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