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Saskatchewan

$141+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
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 November 4, 2025.

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.
Mon 12/297:38 pmORD - YXE
1 stop19h 00mMultiple Airlines
Mon 1/56:25 amYXE - ORD
1 stop7h 10mMultiple Airlines
Deal found 11/3$321
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.
Mon 12/18:22 pmORD - YQR
1 stop21h 58mMultiple Airlines
Mon 12/86:10 amYQR - ORD
1 stop7h 25mMultiple Airlines
Deal found 11/2$346
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 12/288:19 amORD - YXE
1 stop6h 19mMultiple Airlines
Mon 1/56:25 amYXE - ORD
1 stop7h 10mMultiple Airlines
Deal found 11/3$350
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 12/306:44 pmORD - YXE
2 stops31h 05mMultiple Airlines
Mon 1/56:25 amYXE - ORD
1 stop7h 10mMultiple Airlines
Deal found 11/3$365
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 12/3012:32 pmORD - YXE
2 stops35h 46mMultiple Airlines
Sun 1/49:45 pmYXE - ORD
1 stop15h 50mMultiple Airlines
Deal found 11/3$501
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:35 amORD - YXE
1 stop8h 03mDelta
Mon 1/56:25 amYXE - ORD
1 stop7h 10mDelta
Deal found 11/3$546
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:41 amORD - YXE
3 stops30h 18mWestJet
Sun 1/49:45 pmYXE - ORD
1 stop15h 50mWestJet
Deal found 11/3$548
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:41 amORD - YXE
3 stops30h 18mWestJet
Mon 1/56:25 amYXE - ORD
1 stop7h 10mWestJet
Deal found 11/3$552
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:35 amORD - YXE
1 stop8h 03mDelta
Sun 1/48:10 amYXE - ORD
1 stop13h 24mDelta
Deal found 11/3$622
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/68:50 amORD - YQR
2 stops14h 01mUnited Airlines
Tue 11/1110:45 amYQR - ORD
2 stops22h 56mUnited Airlines
Deal found 11/3$838
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/3012:15 amORD - YQR
1 stop22h 36mUnited Airlines
Mon 12/810:53 amYQR - ORD
1 stop13h 06mUnited Airlines
Deal found 11/2$883
This FlightHub deal was found by Cheapflights users on 11/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:08 amORD - YQR
1 stop12h 12mWestJet
Tue 11/1111:05 amYQR - ORD
2 stops29h 47mWestJet
Deal found 11/4$1,035

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 November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$287
(Trip.com)

One-way from

$141
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$862
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 November 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 November 4, 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

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 4/7

3:55 pm-9:36 pm

1 stop6h 41m

Regina

Wed 4/8

9:45 am-9:13 pm

1 stop10h 28m

$335

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Tue 1/20

8:00 am-2:35 pm

1 stop6h 35m

Saskatoon

Wed 1/28

6:00 am-1:01 pm

1 stop7h 01m

$339

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Mon 3/2

2:20 pm-12:45 am

2 stops34h 25m

Saskatoon

Mon 3/9

5:25 am-1:35 pm

1 stop7h 10m

$339

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Sun 12/28

8:19 am-2:38 pm

1 stop6h 19m

Saskatoon

Mon 1/5

6:25 am-1:35 pm

1 stop7h 10m

$350

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 12/1

8:22 pm-6:20 pm

1 stop21h 58m

Regina

Mon 12/8

9:45 pm-3:12 pm

2 stops17h 27m

$353

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Mon 12/29

7:38 pm-2:38 pm

1 stop19h 00m

Saskatoon

Mon 1/5

4:30 pm-12:01 am

2 stops31h 31m

$377

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Tue 1/20

8:50 am-2:38 pm

1 stop5h 48m

Saskatoon

Wed 1/28

7:00 am-9:04 pm

2 stops14h 04m

$458

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Tue 4/7

7:55 am-1:31 pm

1 stop6h 36m

Saskatoon

Wed 4/8

5:00 am-1:00 pm

1 stop7h 00m

$469

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Tue 12/30

12:32 pm-12:18 am

2 stops35h 46m

Saskatoon

Sun 1/4

9:45 pm-1:35 pm

1 stop15h 50m

$501

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 4/7

4:15 pm-10:13 pm

1 stop6h 58m

Regina

Wed 4/8

5:00 am-7:50 pm

2 stops13h 50m

$559

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 26 results
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2
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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 November 4, 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.

How much does it cost to fly round-trip from Chicago to Saskatchewan?

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, 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
8,002 reviews

Food

7.3

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

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
8,002 reviews
Delta
7.9
Good
8,002 reviews

Food

7.3

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

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
3,153 reviews
Delta
7.9
Good
8,002 reviews

Food

7.3

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

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 6h 35m. There are 1124 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?

    $143 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Delta and Air Canada, with prices starting from $184 and $215, 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 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.

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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$245Average$565FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$284Average$466FlexibilityNo cancel feeOn-time69%
WestJetCheapest$289Average$385FlexibilityNo cancel feeOn-time60%
DeltaCheapest$327Average$540FlexibilityNo cancel feeOn-timeN/A

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