HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Saskatchewan

$108+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

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

Keep the following information in mind while searching for Chicago to Saskatchewan flight deals. Data was last updated August 18, 2025.

Round-trip from

$206
(Trip.com)

One-way from

$108
(Kiwi.com)
From Chicago (CHI) to Saskatchewan
Search Deals
One-way flight from Chicago (CHI) to Saskatchewan
Search Deals

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 August 18, 2025.

This Trip.com deal was found by Cheapflights users on 8/17. 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 10/312:20 pmORD - YXE
1 stop6h 39mWestJet
Mon 11/36:25 amYXE - ORD
1 stop7h 10mWestJet
Deal found 8/17$206
This oojo deal was found by Cheapflights users on 8/16. 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 12/52:20 pmORD - YXE
1 stop6h 39mWestJet
Mon 12/86:25 amYXE - ORD
1 stop7h 10mWestJet
Deal found 8/16$225
This Trip.com deal was found by Cheapflights users on 8/16. 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 9/185:30 pmORD - YXE
1 stop8h 23mWestJet
Tue 9/236:00 amYXE - ORD
1 stop9h 43mWestJet
Deal found 8/16$234
This Trip.com deal was found by Cheapflights users on 8/17. 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 9/155:30 pmORD - YXE
1 stop8h 23mWestJet
Mon 9/228:50 pmYXE - ORD
1 stop18h 53mWestJet
Deal found 8/17$236
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/165:30 pmORD - YXE
1 stop8h 23mWestJet
Mon 9/223:45 pmYXE - ORD
2 stops23h 58mWestJet
Deal found 8/16$256
This FlightHub deal was found by Cheapflights users on 8/16. 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.
Thu 9/185:30 pmORD - YXE
1 stop8h 23mWestJet
Mon 9/2211:15 amYXE - ORD
1 stop28h 28mWestJet
Deal found 8/16$257
This FlightHub deal was found by Cheapflights users on 8/16. 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.
Tue 9/165:30 pmORD - YXE
1 stop8h 23mWestJet
Tue 9/235:20 amYXE - ORD
2 stops10h 23mWestJet
Deal found 8/16$260
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/131:40 pmORD - YXE
1 stop19h 37mMultiple Airlines
Sat 9/206:00 amYXE - ORD
2 stops12h 50mMultiple Airlines
Deal found 8/16$273
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/201:40 pmORD - YXE
1 stop19h 37mWestJet
Tue 9/236:00 amYXE - ORD
1 stop9h 43mWestJet
Deal found 8/16$274
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 10/217:15 amORD - YQR
2 stops34h 16mMultiple Airlines
Sat 10/258:35 pmYQR - ORD
1 stop16h 00mMultiple Airlines
Deal found 8/15$282
This Air Canada deal was found by Cheapflights users on 8/15. 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 11/63:55 pmORD - YQR
1 stop7h 24mAir Canada
Tue 11/115:00 amYQR - ORD
1 stop8h 01mAir Canada
Deal found 8/15$325
This United Airlines deal was found by Cheapflights users on 8/17. 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 11/62:40 pmORD - YQR
1 stop8h 11mUnited Airlines
Tue 11/1110:45 amYQR - ORD
1 stop6h 13mUnited Airlines
Deal found 8/17$327

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 August 18, 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 10/31

2:20 pm-7:59 pm

1 stop6h 39m

Saskatoon

Mon 11/3

6:25 am-1:35 pm

1 stop7h 10m

$206

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Fri 12/5

2:20 pm-8:59 pm

1 stop6h 39m

Saskatoon

Mon 12/8

6:25 am-1:35 pm

1 stop7h 10m

$225

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Thu 9/18

5:30 pm-12:53 am

1 stop8h 23m

Saskatoon

Tue 9/23

6:00 am-4:43 pm

1 stop9h 43m

$234

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Mon 9/15

5:30 pm-12:53 am

1 stop8h 23m

Saskatoon

Mon 9/22

8:50 pm-4:43 pm

1 stop18h 53m

$236

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Tue 9/16

5:30 pm-12:53 am

1 stop8h 23m

Saskatoon

Mon 9/22

3:45 pm-4:43 pm

2 stops23h 58m

$256

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Thu 9/18

5:30 pm-12:53 am

1 stop8h 23m

Saskatoon

Mon 9/22

11:15 am-4:43 pm

1 stop28h 28m

$257

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Tue 9/16

5:30 pm-12:53 am

1 stop8h 23m

Saskatoon

Tue 9/23

5:20 am-4:43 pm

2 stops10h 23m

$260

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Sat 9/13

1:40 pm-8:17 am

1 stop19h 37m

Saskatoon

Sat 9/20

6:00 am-7:50 pm

2 stops12h 50m

$273

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 10/21

7:15 am-4:31 pm

2 stops34h 16m

Regina

Sat 10/25

8:35 pm-1:35 pm

1 stop16h 00m

$282

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 10/21

2:53 pm-9:36 pm

1 stop7h 43m

Regina

Fri 10/24

11:25 am-7:29 pm

1 stop7h 04m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

Showing 1-10 of 39 results
1
2
3
4

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 August 18, 2025.

When flying from Chicago to Saskatchewan, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 18, 2025.
Get a feel of what it's like to fly with Delta, 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.
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
3,018 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Canada
7.1
Good
9,992 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

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

    $108 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on Air Canada and United Airlines, with prices starting from $112 and $139, 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 - 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.

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

    Currently, February is the cheapest month in which you can book a flight from Chicago to Saskatchewan (average of $323). Flying from Chicago to Saskatchewan in April is currently the most expensive (average of $559). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Saskatchewan

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Pearson Intl flights
O'Hare Intl to Vancouver Intl flights
O'Hare Intl to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Calgary flights
Midway to Pearson Intl flights
Midway to Vancouver Intl flights
Midway to Toronto Island flights
O'Hare Intl to Toronto Island flights
Midway to Pierre Elliott Trudeau Intl flights
St. Louis to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Québec City flights
Midway to Calgary flights
O'Hare Intl to Abbotsford flights
St. Louis to Pearson Intl flights
O'Hare Intl to Ottawa flights
O'Hare Intl to Winnipeg flights
O'Hare Intl to Halifax flights
Midway to Québec City flights
O'Hare Intl to Edmonton flights
St. Louis to Vancouver Intl flights
Midway to Edmonton flights
St. Louis to Calgary flights
Midway to Ottawa flights
Midway to Halifax flights
O'Hare Intl to Hamilton flights
St. Louis to Québec City flights
O'Hare Intl to Victoria flights
Midway to Winnipeg flights
O'Hare Intl to Charlottetown flights
O'Hare Intl to St. John's flights
St. Louis to Winnipeg flights
St. Louis to Halifax flights
Midway to Victoria flights
O'Hare Intl to Kelowna flights
O'Hare Intl to Saskatoon flights
St. Louis to Edmonton flights
Midway to Kelowna flights
Moline to Pearson Intl flights
St. Louis to St. John's flights
O'Hare Intl to Deer Lake flights
Midway to St. John's flights
Midway to Saskatoon flights
O'Hare Intl to London flights
O'Hare Intl to Whitehorse flights
St. Louis to Saskatoon flights
Peoria to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Regina flights
O'Hare Intl to Thunder Bay flights

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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$284Average$380FlexibilityNo cancel feeOn-time69%
WestJetCheapest$289Average$385FlexibilityNo cancel feeOn-time60%
DeltaCheapest$327Average$565FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$365Average$567FlexibilityNo cancel feeOn-time67%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.