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Saskatchewan

$101+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$241
(oojo)

One-way from

$101
(United Airlines)
Provider with most accurate pricing for Chicago (CHI)-Saskatoon flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Saskatoon flights.
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From Chicago (CHI) to Saskatchewan
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One-way flight from Chicago (CHI) to Saskatchewan
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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 January 8, 2026.

This FlightHub deal was found by Cheapflights users on 1/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/62:20 pmORD - YQR
1 stop6h 46mWestJet
Mon 2/96:10 amYQR - ORD
1 stop7h 25mWestJet
Deal found 1/6$183
This FlightHub deal was found by Cheapflights users on 1/7. 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.
Mon 7/135:30 pmORD - YXE
1 stop8h 23mWestJet
Fri 7/177:00 amYXE - ORD
1 stop8h 43mWestJet
Deal found 1/7$221
This oojo deal was found by Cheapflights users on 1/6. 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.
Fri 2/202:20 pmORD - YXE
1 stop21h 01mWestJet
Fri 2/276:25 amYXE - ORD
1 stop7h 10mWestJet
Deal found 1/6$241
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/302:20 pmORD - YQR
1 stop6h 48mMultiple Airlines
Mon 2/210:40 amYQR - ORD
2 stops27h 58mMultiple Airlines
Deal found 1/6$242
This United Airlines deal was found by Cheapflights users on 1/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/307:00 amORD - YQR
1 stop15h 51mUnited Airlines
Mon 2/210:45 amYQR - ORD
1 stop13h 14mUnited Airlines
Deal found 1/6$244
This Air Canada deal was found by Cheapflights users on 1/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/223:55 pmORD - YQR
1 stop7h 24mAir Canada
Mon 1/265:00 amYQR - ORD
2 stops9h 55mAir Canada
Deal found 1/5$254
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/298:00 amORD - YQR
2 stops15h 51mMultiple Airlines
Sun 2/19:45 pmYQR - ORD
1 stop15h 50mMultiple Airlines
Deal found 1/7$321
This United Airlines deal was found by Cheapflights users on 1/7. 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.
Thu 1/291:55 pmORD - YQR
1 stop8h 56mUnited Airlines
Sun 2/15:00 amYQR - ORD
1 stop14h 45mUnited Airlines
Deal found 1/7$342
This Delta deal was found by Cheapflights users on 1/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/71:55 pmORD - YXE
2 stops11h 35mDelta
Tue 2/108:10 amYXE - ORD
1 stop9h 45mDelta
Deal found 1/6$345
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/202:20 pmORD - YXE
1 stop21h 01mMultiple Airlines
Fri 2/274:45 pmYXE - ORD
2 stops24h 08mMultiple Airlines
Deal found 1/6$356
This Delta deal was found by Cheapflights users on 1/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:55 amORD - YXE
2 stops14h 48mDelta
Fri 7/177:00 amYXE - ORD
2 stops10h 41mDelta
Deal found 1/7$371
This Air Canada deal was found by Cheapflights users on 1/7. 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.
Tue 4/78:20 pmORD - YXE
1 stop14h 06mAir Canada
Wed 4/82:30 pmYXE - ORD
2 stops20h 47mAir Canada
Deal found 1/7$383

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 January 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

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 2/6

2:20 pm-9:06 pm

1 stop6h 46m

Regina

Mon 2/9

6:10 am-1:35 pm

1 stop7h 25m

$183

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Fri 2/20

2:20 pm-11:21 am

1 stop21h 01m

Saskatoon

Fri 2/27

6:25 am-1:35 pm

1 stop7h 10m

$241

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 1/30

2:20 pm-9:08 pm

1 stop6h 48m

Regina

Mon 2/2

10:40 am-2:38 pm

2 stops27h 58m

$242

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 1/30

7:00 am-10:51 pm

1 stop15h 51m

Regina

Mon 2/2

10:45 am-11:59 pm

1 stop13h 14m

$244

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 1/22

3:55 pm-11:19 pm

1 stop7h 24m

Regina

Mon 1/26

5:00 am-2:55 pm

2 stops9h 55m

$254

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 1/29

8:00 am-11:51 pm

2 stops15h 51m

Regina

Sun 2/1

9:45 pm-1:35 pm

1 stop15h 50m

$321

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 1/29

1:55 pm-10:51 pm

1 stop8h 56m

Regina

Sun 2/1

5:00 am-7:45 pm

1 stop14h 45m

$342

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Sat 2/7

1:55 pm-1:30 am

2 stops11h 35m

Saskatoon

Tue 2/10

8:10 am-5:55 pm

1 stop9h 45m

$345

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Fri 2/20

2:20 pm-11:21 am

1 stop21h 01m

Saskatoon

Fri 2/27

4:45 pm-4:53 pm

2 stops24h 08m

$356

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Tue 4/7

8:20 pm-9:26 am

1 stop14h 06m

Saskatoon

Wed 4/8

2:30 pm-12:17 pm

2 stops20h 47m

$383

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 35 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 January 8, 2026.
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
8,029 reviews

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Crew

8.5

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
8,029 reviews
Delta
7.9
Good
8,029 reviews

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Crew

8.5

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
3,235 reviews
Delta
7.9
Good
8,029 reviews

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Crew

8.5

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 46m. There are 987 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 - 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

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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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$188Average$475FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$284Average$466FlexibilityNo cancel feeOn-time69%
WestJetCheapest$289Average$385FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$365Average$661FlexibilityNo cancel feeOn-time67%

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