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Saskatchewan

$176+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
Jul 1 — Jul 81
Tue 7/1
Tue 7/8
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 June 26, 2025.

Round-trip from

$327
(oojo)

One-way from

$176
(oojo)
From Chicago (CHI) to Saskatchewan
Search Deals
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 June 26, 2025.

This oojo deal was found by Cheapflights users on 6/24. 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.
Sat 9/65:30 pmORD - YXE
1 stop8h 23mWestJet
Wed 9/107:55 amYXE - ORD
1 stop7h 48mWestJet
Deal found 6/24$327
This Gotogate deal was found by Cheapflights users on 6/23. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/205:30 pmORD - YQR
1 stop6h 31mWestJet
Sat 9/276:55 amYQR - ORD
1 stop8h 48mWestJet
Deal found 6/23$343
This Flightnetwork deal was found by Cheapflights users on 6/24. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/86:20 pmORD - YXE
1 stop6h 36mAir Canada
Fri 8/156:00 amYXE - ORD
1 stop8h 04mAir Canada
Deal found 6/24$360
This Flightnetwork deal was found by Cheapflights users on 6/24. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/115:30 pmORD - YXE
1 stop8h 24mMultiple Airlines
Tue 8/196:00 amYXE - ORD
1 stop8h 04mMultiple Airlines
Deal found 6/24$369
This Mytrip deal was found by Cheapflights users on 6/23. 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.
Sat 9/203:21 pmORD - YQR
2 stops21h 05mMultiple Airlines
Sat 9/276:55 amYQR - ORD
1 stop8h 48mMultiple Airlines
Deal found 6/23$381
This Flightnetwork deal was found by Cheapflights users on 6/25. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/99:55 amORD - YQR
1 stop9h 18mAir Canada
Sat 8/167:00 amYQR - ORD
1 stop7h 04mAir Canada
Deal found 6/25$396
This United Airlines deal was found by Cheapflights users on 6/24. 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 8/84:20 pmORD - YQR
1 stop6h 16mUnited Airlines
Fri 8/159:45 amYQR - ORD
1 stop7h 39mUnited Airlines
Deal found 6/24$454
This Delta deal was found by Cheapflights users on 6/25. 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 9/276:00 amORD - YXE
2 stops13h 03mDelta
Sun 10/55:40 amYXE - ORD
2 stops11h 58mDelta
Deal found 6/25$526
This Delta deal was found by Cheapflights users on 6/24. 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 9/61:43 pmMDW - YXE
1 stop8h 41mDelta
Wed 9/106:00 amYXE - MDW
2 stops11h 37mDelta
Deal found 6/24$527
This Mytrip deal was found by Cheapflights users on 6/25. 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 7/239:40 amMDW - YXE
3 stops16h 14mMultiple Airlines
Thu 7/246:50 pmYXE - MDW
3 stops20h 34mMultiple Airlines
Deal found 6/25$664
This Delta deal was found by Cheapflights users on 6/25. 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 11/66:00 amORD - YQR
2 stops11h 35mDelta
Tue 11/1111:45 amYQR - ORD
2 stops10h 01mDelta
Deal found 6/25$744
This oojo deal was found by Cheapflights users on 6/25. 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.
Wed 8/69:24 amMDW - YXE
1 stop13h 01mWestJet
Tue 8/123:15 pmYXE - MDW
1 stop25h 22mWestJet
Deal found 6/25$775

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 June 26, 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

Sat 9/6

5:30 pm-12:53 am

1 stop8h 23m

Saskatoon

Wed 9/10

7:55 am-4:43 pm

1 stop7h 48m

$327

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 9/20

5:30 pm-11:01 pm

1 stop6h 31m

Regina

Sat 9/27

6:55 am-4:43 pm

1 stop8h 48m

$343

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Fri 8/8

6:20 pm-11:56 pm

1 stop6h 36m

Saskatoon

Fri 8/15

6:00 am-3:04 pm

1 stop8h 04m

$360

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Mon 8/11

5:30 pm-12:54 am

1 stop8h 24m

Saskatoon

Tue 8/19

6:00 am-3:04 pm

1 stop8h 04m

$369

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 9/20

3:21 pm-11:26 am

2 stops21h 05m

Regina

Sat 9/27

6:55 am-4:43 pm

1 stop8h 48m

$381

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 8/9

9:55 am-6:13 pm

1 stop9h 18m

Regina

Sat 8/16

7:00 am-3:04 pm

1 stop7h 04m

$396

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 8/8

4:20 pm-9:36 pm

1 stop6h 16m

Regina

Fri 8/15

9:45 am-6:24 pm

1 stop7h 39m

$454

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Sat 9/27

6:00 am-6:03 pm

2 stops13h 03m

Saskatoon

Sun 10/5

5:40 am-6:38 pm

2 stops11h 58m

$526

ChicagoSaskatoon

MDW - YXE

MDWYXE

Chicago Midway

Sat 9/6

1:43 pm-9:24 pm

1 stop8h 41m

Saskatoon

Wed 9/10

6:00 am-6:37 pm

2 stops11h 37m

$527

ChicagoSaskatoon

MDW - YXE

MDWYXE

Chicago Midway

Wed 7/23

9:40 am-12:54 am

3 stops16h 14m

Saskatoon

Thu 7/24

6:50 pm-4:24 pm

3 stops20h 34m

$664

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/25

Showing 1-10 of 21 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 June 26, 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.

Rainfall in Saskatchewan by month

Plan your trip to Saskatchewan by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Saskatchewan ranges from 0.4 - 2.5 inches per month. June is typically the wettest month, when rainfall can reach 2.5 in. February is typically the driest time to visit Saskatchewan when rainfall is around 0.4 in.

Temperature in Saskatchewan by month

Plan your trip to Saskatchewan by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Saskatchewan, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 66.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 6.8 F).

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 June 26, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, 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
7,966 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

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
7,966 reviews
Delta
8.0
Very good
7,966 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

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!
United Airlines
7.4
Good
8,840 reviews
Delta
8.0
Very good
7,966 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

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
2,891 reviews
Delta
8.0
Very good
7,966 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

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
9,629 reviews
Delta
8.0
Very good
7,966 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

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?

    $176 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 Delta, with prices starting from $206 and $263, 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

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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 June 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$282Average$457FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$284Average$380FlexibilityNo cancel feeOn-time69%
WestJetCheapest$295Average$422FlexibilityNo cancel feeOn-time60%
DeltaCheapest$327Average$591FlexibilityNo cancel feeOn-timeN/A

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