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Saskatchewan

$186+ 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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
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 enero 21, 2025.

Round-trip from

$284
(Kiwi.com)

One-way from

$186
(Trip.com)
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 enero 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
jue. 4/34:45 pmORD - YQR
1 stop7h 35mMultiple Airlines
mar. 4/811:15 amYQR - ORD
2 stops12h 48mMultiple Airlines
Deal found 1/19$284
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
lun. 3/34:45 pmORD - YXE
1 stop9h 03mMultiple Airlines
lun. 3/104:20 pmYXE - ORD
2 stops13h 16mMultiple Airlines
Deal found 1/21$293
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
lun. 3/34:45 pmORD - YXE
1 stop15h 36mWestJet
lun. 3/105:30 amYXE - ORD
1 stop9h 26mWestJet
Deal found 1/21$323
This United deal was found by Cheapflights users on 1/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/911:55 amORD - YQR
1 stop7h 18mUnited Airlines
mar. 7/159:45 amYQR - ORD
1 stop11h 40mUnited Airlines
Deal found 1/21$376
This Air Canada deal was found by Cheapflights users on 1/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/289:15 pmORD - YXE
1 stop14h 32mAir Canada
mié. 6/46:00 amYXE - ORD
1 stop7h 55mAir Canada
Deal found 1/21$392
This Booking.com deal was found by Cheapflights users on 1/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/64:45 pmORD - YQR
1 stop9h 11mWestJet
jue. 3/138:15 amYQR - ORD
1 stop6h 41mWestJet
Deal found 1/20$419
This Air Canada deal was found by Cheapflights users on 1/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/911:55 amORD - YQR
1 stop7h 18mAir Canada
mar. 7/157:15 pmYQR - ORD
2 stops13h 39mAir Canada
Deal found 1/21$424
This Trip.com deal was found by Cheapflights users on 1/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/79:33 amMDW - YXE
2 stops15h 41mWestJet
vie. 3/144:45 amYXE - MDW
2 stops27h 00mWestJet
Deal found 1/21$592
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/412:15 pmORD - YQR
1 stop5h 21mDelta
mar. 3/1110:45 amYQR - ORD
2 stops12h 11mDelta
Deal found 1/20$735

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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

jue. 4/3

4:45 pm-11:20 pm

1 stop7h 35m

Regina

mar. 4/8

11:15 am-1:03 am

2 stops12h 48m

$284

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

lun. 3/3

4:45 pm-1:48 am

1 stop9h 03m

Saskatoon

lun. 3/10

4:20 pm-6:36 am

2 stops13h 16m

$293

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

lun. 3/3

4:45 pm-8:21 am

1 stop15h 36m

Saskatoon

lun. 3/10

5:30 am-3:56 pm

1 stop9h 26m

$323

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

mié. 7/9

11:55 am-6:13 pm

1 stop7h 18m

Regina

mar. 7/15

9:45 am-10:25 pm

1 stop11h 40m

$376

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

mié. 5/28

9:15 pm-10:47 am

1 stop14h 32m

Saskatoon

mié. 6/4

6:00 am-2:55 pm

1 stop7h 55m

$392

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

jue. 3/6

4:45 pm-1:56 am

1 stop9h 11m

Regina

jue. 3/13

8:15 am-3:56 pm

1 stop6h 41m

$419

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

mié. 7/9

11:55 am-6:13 pm

1 stop7h 18m

Regina

mar. 7/15

7:15 pm-9:54 am

2 stops13h 39m

$424

ChicagoSaskatoon

MDW - YXE

MDWYXE

Chicago Midway

vie. 3/7

9:33 am-1:14 am

2 stops15h 41m

Saskatoon

vie. 3/14

4:45 am-8:45 am

2 stops27h 00m

$592

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

mar. 3/4

12:15 pm-5:36 pm

1 stop5h 21m

Regina

mar. 3/11

10:45 am-11:56 pm

2 stops12h 11m

$735

ChicagoSaskatoon

MDW - YXE

MDWYXE

Chicago Midway

jue. 2/20

1:05 pm-1:14 am

1 stop12h 09m

$186

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 13 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.

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 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 enero 21, 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 0.0 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. February is typically the driest time to visit Saskatchewan when rainfall is around 0.0 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 64.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 1.4 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 enero 21, 2025.
Peruse reviews from past customers who have flown with WestJet and Air Canada 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
8,521 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.9

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
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.9

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
8,985 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.9

Reviews

1 / 10

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

WestJet
7.2
Good
2,829 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.9

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
8,635 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.9

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 - 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.

  • 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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$222Average$510FlexibilityNo cancel feeOn-time67%
WestJetCheapest$366Average$651FlexibilityNo cancel feeOn-time60%
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