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$342+ Cheap flights from Chicago (CHI) to Saskatchewan

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
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Cheap flight deals from Chicago to Saskatchewan

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Saskatchewan (CASK). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 22, 2024.

Round-trip from

$342
(Mytrip)
From Chicago (CHI) to Saskatchewan
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Find flight deals from Chicago to Saskatchewan

Best flights from Chicago to Saskatchewan
Discover carefully curated flight deals from Chicago to Saskatchewan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 22, 2024.

This Mytrip deal was found by Cheapflights users on 12/20. 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 2/42:05 pmORD - YQR
2 stops18h 33mMultiple Airlines
Tue 2/119:45 pmYQR - ORD
2 stops17h 06mMultiple Airlines
Deal found 12/20$342
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Wed 5/282:18 pmORD - YQR
1 stop8h 16mUnited Airlines
Fri 6/69:45 amYQR - ORD
1 stop11h 40mUnited Airlines
Deal found 12/21$352
This oojo deal was found by Cheapflights users on 12/21. 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 5/285:30 pmORD - YQR
1 stop8h 37mWestJet
Fri 6/610:05 amYQR - ORD
2 stops29h 39mWestJet
Deal found 12/21$407
This Flightnetwork deal was found by Cheapflights users on 12/20. 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.
Tue 2/44:00 pmORD - YQR
1 stop7h 18mAir Canada
Tue 2/116:45 amYQR - ORD
1 stop6h 26mAir Canada
Deal found 12/20$467
This Delta deal was found by Cheapflights users on 12/21. 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 2/46:15 amORD - YXE
1 stop8h 35mDelta
Tue 2/118:10 amYXE - ORD
1 stop9h 19mDelta
Deal found 12/21$491
This Mytrip deal was found by Cheapflights users on 12/21. 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 6/105:30 pmORD - YXE
1 stop8h 24mMultiple Airlines
Wed 6/183:45 pmYXE - ORD
2 stops26h 26mMultiple Airlines
Deal found 12/21$445
This Mytrip deal was found by Cheapflights users on 12/21. 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 6/105:30 pmORD - YXE
1 stop8h 24mWestJet
Wed 6/187:55 amYXE - ORD
1 stop7h 49mWestJet
Deal found 12/21$477
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 1/181:05 pmMDW - YXE
1 stop12h 12mMultiple Airlines
Sat 1/254:30 pmYXE - MDW
1 stop19h 40mMultiple Airlines
Deal found 12/21$460
This Delta deal was found by Cheapflights users on 12/21. 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 2/41:26 pmMDW - YXE
2 stops12h 24mDelta
Tue 2/118:10 amYXE - MDW
1 stop9h 33mDelta
Deal found 12/21$554
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Sat 1/184:00 pmORD - YXE
1 stop7h 44mUnited Airlines
Sat 1/257:00 amYXE - ORD
1 stop7h 51mUnited Airlines
Deal found 12/21$772
This Justfly.com deal was found by Cheapflights users on 12/21. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/191:00 pmMDW - YXE
2 stops10h 44mWestJet
Thu 6/265:40 amYXE - MDW
2 stops10h 21mWestJet
Deal found 12/21$752

Find flights from Chicago to Saskatchewan within your budget

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 2/4

2:05 pm-8:38 am

2 stops18h 33m

Regina

Tue 2/11

9:45 pm-2:51 pm

2 stops17h 06m

$342

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 5/28

2:18 pm-9:34 pm

1 stop8h 16m

Regina

Fri 6/6

9:45 am-10:25 pm

1 stop11h 40m

$352

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 5/13

11:55 am-6:13 pm

1 stop7h 18m

Regina

Sun 5/18

7:15 pm-10:01 am

1 stop13h 46m

$371

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 5/28

5:30 pm-1:07 am

1 stop8h 37m

Regina

Fri 6/6

10:05 am-4:44 pm

2 stops29h 39m

$407

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Tue 6/10

5:30 pm-12:54 am

1 stop8h 24m

Saskatoon

Wed 6/18

3:45 pm-7:11 pm

2 stops26h 26m

$445

ChicagoSaskatoon

MDW - YXE

MDWYXE

Chicago Midway

Sat 1/18

1:05 pm-1:17 am

1 stop12h 12m

Saskatoon

Sat 1/25

4:30 pm-12:10 pm

1 stop19h 40m

$460

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Tue 6/10

5:30 pm-12:54 am

1 stop8h 24m

Saskatoon

Wed 6/18

7:55 am-4:44 pm

1 stop7h 49m

$477

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Tue 2/4

6:15 am-2:50 pm

1 stop8h 35m

Saskatoon

Tue 2/11

8:10 am-5:29 pm

1 stop9h 19m

$491

ChicagoSaskatoon

MDW - YXE

MDWYXE

Chicago Midway

Tue 2/4

1:26 pm-1:50 am

2 stops12h 24m

Saskatoon

Tue 2/11

8:10 am-5:43 pm

1 stop9h 33m

$554

ChicagoSaskatoon

MDW - YXE

MDWYXE

Chicago Midway

Thu 6/19

1:00 pm-10:44 pm

2 stops10h 44m

Saskatoon

Thu 6/26

5:40 am-5:01 pm

2 stops10h 21m

$752

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 12 results
1
2

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.

Travel insights for flights from Chicago to Saskatchewan

Get recent, data-driven insights about flights from Chicago to Saskatchewan including ideal travel times, pricing trends, and more.

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

Currently, October is the cheapest month in which you can book a flight from Chicago to Saskatchewan (average of $428). Flying from Chicago to Saskatchewan in May is currently the most expensive (average of $560). 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.

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 December 22, 2024.

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 December 22, 2024.
Peruse reviews from past customers who have flown with Delta, WestJet and United Airlines from Chicago to Saskatchewan to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,594 reviews

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.9

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,594 reviews
Delta
8.0
Very good
8,594 reviews

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.9

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines
7.4
Good
9,028 reviews
Delta
8.0
Very good
8,594 reviews

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.9

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

WestJet
7.3
Good
2,812 reviews
Delta
8.0
Very good
8,594 reviews

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.9

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Air Canada
7.0
Good
8,413 reviews
Delta
8.0
Very good
8,594 reviews

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.9

Boarding

8.2

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 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, October is the cheapest month in which you can book a flight from Chicago to Saskatchewan (average of $428). Flying from Chicago to Saskatchewan in May is currently the most expensive (average of $560). 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 2 airlines flying from Chicago to Saskatchewan

Discover the top 2 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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$261Average$532FlexibilityNo cancel feeOn-time67%
WestJetCheapest$366Average$651FlexibilityNo cancel feeOn-time60%
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