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Saskatchewan

$95+ 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 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Find 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 October 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/14. 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 11/282:20 pmORD - YXE
1 stop9h 58mWestJet
Fri 12/56:25 amYXE - ORD
1 stop7h 10mWestJet
Deal found 10/14$201
This United Airlines deal was found by Cheapflights users on 10/14. 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 10/301:55 pmORD - YQR
1 stop8h 56mUnited Airlines
Tue 11/410:45 amYQR - ORD
1 stop12h 05mUnited Airlines
Deal found 10/14$234
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 11/279:20 amORD - YXE
1 stop5h 18mMultiple Airlines
Thu 12/49:45 pmYXE - ORD
1 stop15h 50mMultiple Airlines
Deal found 10/13$235
This FlightHub deal was found by Cheapflights users on 10/14. 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 11/142:20 pmORD - YXE
1 stop11h 29mWestJet
Sun 11/169:45 pmYXE - ORD
1 stop15h 50mWestJet
Deal found 10/14$252
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 11/145:11 amORD - YXE
2 stops13h 51mMultiple Airlines
Sun 11/168:10 amYXE - ORD
1 stop9h 22mMultiple Airlines
Deal found 10/14$277
This Mytrip deal was found by Cheapflights users on 10/14. 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 11/2811:00 amORD - YXE
3 stops14h 49mMultiple Airlines
Fri 12/54:45 pmYXE - ORD
2 stops13h 15mMultiple Airlines
Deal found 10/14$327
This Delta deal was found by Cheapflights users on 10/14. 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 11/68:57 amORD - YQR
1 stop9h 23mDelta
Tue 11/1111:40 amYQR - ORD
1 stop9h 56mDelta
Deal found 10/14$335
This Mytrip deal was found by Cheapflights users on 10/13. 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.
Wed 11/125:10 amORD - YXE
2 stops20h 39mMultiple Airlines
Sat 12/134:45 pmYXE - ORD
2 stops13h 15mMultiple Airlines
Deal found 10/13$338
This Delta deal was found by Cheapflights users on 10/13. 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 11/279:41 amMDW - YXE
1 stop4h 57mDelta
Thu 12/47:00 amYXE - MDW
2 stops11h 00mDelta
Deal found 10/13$411
This Delta deal was found by Cheapflights users on 10/12. 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 10/302:20 pmORD - YQR
1 stop10h 10mDelta
Tue 11/411:40 amYQR - ORD
2 stops12h 18mDelta
Deal found 10/12$421
This Delta deal was found by Cheapflights users on 10/14. 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 11/289:41 amMDW - YXE
2 stops9h 21mDelta
Fri 12/57:00 amYXE - MDW
2 stops11h 00mDelta
Deal found 10/14$469
This Mytrip deal was found by Cheapflights users on 10/14. 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 11/289:41 amMDW - YXE
2 stops15h 52mWestJet
Fri 12/54:45 pmYXE - MDW
3 stops25h 33mWestJet
Deal found 10/14$533

Cheap 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 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$234
(United Airlines)

One-way from

$95
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$515
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. 22% potential increase in price ($158 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 14, 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

Fri 11/28

2:20 pm-12:18 am

1 stop9h 58m

Saskatoon

Fri 12/5

6:25 am-1:35 pm

1 stop7h 10m

$201

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 10/30

2:40 pm-9:51 pm

1 stop8h 11m

Regina

Tue 11/4

10:45 am-6:53 pm

1 stop8h 08m

$234

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Thu 11/27

9:20 am-2:38 pm

1 stop5h 18m

Saskatoon

Thu 12/4

9:45 pm-1:35 pm

1 stop15h 50m

$235

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Fri 11/14

2:20 pm-1:49 am

1 stop11h 29m

Saskatoon

Sun 11/16

9:45 pm-1:35 pm

1 stop15h 50m

$252

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Fri 11/14

5:11 am-7:02 pm

2 stops13h 51m

Saskatoon

Sun 11/16

8:10 am-5:32 pm

1 stop9h 22m

$277

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Fri 11/28

11:00 am-1:49 am

3 stops14h 49m

Saskatoon

Fri 12/5

4:45 pm-6:00 am

2 stops13h 15m

$327

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 11/6

8:57 am-6:20 pm

1 stop9h 23m

Regina

Tue 11/11

11:40 am-9:36 pm

1 stop9h 56m

$335

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Sat 11/1

5:05 am-12:49 am

2 stops20h 44m

Saskatoon

Sat 12/13

9:45 pm-8:01 pm

3 stops22h 16m

$391

ChicagoSaskatoon

MDW - YXE

MDWYXE

Chicago Midway

Thu 11/27

9:41 am-2:38 pm

1 stop4h 57m

Saskatoon

Thu 12/4

7:00 am-6:00 pm

2 stops11h 00m

$411

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 10/30

2:20 pm-11:30 pm

1 stop10h 10m

Regina

Tue 11/4

11:40 am-11:58 pm

2 stops12h 18m

$421

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

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 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 October 14, 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 October 14, 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
8.0
Very good
7,972 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
8.0
Very good
7,972 reviews
Delta
8.0
Very good
7,972 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
WestJet
7.2
Good
3,124 reviews
Delta
8.0
Very good
7,972 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 11m. There are 987 mi between Chicago and Saskatchewan. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Saskatchewan one-way?

    $133 is the cheapest one-way deal found within the past few days, from Air Canada. You may also be able to find cheap deals on WestJet and Delta, with prices starting from $141 and $197, respectively.

  • 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 Midway - Saskatoon or Chicago O'Hare Intl - Regina 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

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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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$284Average$392FlexibilityNo cancel feeOn-time69%
WestJetCheapest$289Average$385FlexibilityNo cancel feeOn-time60%
DeltaCheapest$327Average$540FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$365Average$567FlexibilityNo cancel feeOn-time67%

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