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Saskatchewan

$235+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
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 septiembre 15, 2025.

Round-trip from

$237
(United Airlines)

One-way from

$235
(Kiwi.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 septiembre 15, 2025.

This United Airlines deal was found by Cheapflights users on 9/14. 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.
mié. 10/87:10 amORD - YQR
1 stop15h 26mUnited Airlines
mié. 10/1511:25 amYQR - ORD
1 stop6h 59mUnited Airlines
Deal found 9/14$237
This United Airlines deal was found by Cheapflights users on 9/14. 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.
jue. 10/306:28 pmORD - YQR
1 stop16h 11mUnited Airlines
mar. 11/45:00 amYQR - ORD
1 stop7h 05mUnited Airlines
Deal found 9/14$248
This United Airlines deal was found by Cheapflights users on 9/14. 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.
jue. 11/66:28 pmORD - YQR
1 stop16h 11mUnited Airlines
mar. 11/1110:45 amYQR - ORD
1 stop10h 13mUnited Airlines
Deal found 9/14$251
This Kiwi.com deal was found by Cheapflights users on 9/14. 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. 10/302:20 pmORD - YQR
1 stop21h 25mMultiple Airlines
mar. 11/44:25 pmYQR - ORD
2 stops14h 00mMultiple Airlines
Deal found 9/14$275
This Air Canada deal was found by Cheapflights users on 9/14. 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. 10/159:55 amORD - YXE
1 stop15h 02mAir Canada
vie. 10/177:40 pmYXE - ORD
1 stop16h 34mAir Canada
Deal found 9/14$283
This Air Canada deal was found by Cheapflights users on 9/14. 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.
jue. 10/3012:50 pmORD - YQR
2 stops21h 49mAir Canada
mar. 11/45:00 amYQR - ORD
1 stop8h 01mAir Canada
Deal found 9/14$286
This Mytrip deal was found by Cheapflights users on 9/15. 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.
vie. 12/122:20 pmORD - YQR
2 stops44h 12mMultiple Airlines
jue. 12/1811:45 amYQR - ORD
1 stop7h 23mMultiple Airlines
Deal found 9/15$315
This Mytrip deal was found by Cheapflights users on 9/14. 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.
mié. 10/297:43 pmORD - YXE
3 stops30h 06mMultiple Airlines
mié. 11/54:45 pmYXE - ORD
3 stops25h 35mMultiple Airlines
Deal found 9/14$364
This United Airlines deal was found by Cheapflights users on 9/14. 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.
mié. 10/299:20 pmORD - YXE
1 stop13h 15mUnited Airlines
mié. 11/55:05 amYXE - ORD
2 stops17h 45mUnited Airlines
Deal found 9/14$428
This Air Canada deal was found by Cheapflights users on 9/14. 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.
sáb. 9/273:45 pmORD - YXE
1 stop10h 12mAir Canada
dom. 10/57:40 pmYXE - ORD
1 stop13h 15mAir Canada
Deal found 9/14$473
This Air Canada deal was found by Cheapflights users on 9/14. 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. 10/299:20 pmORD - YXE
1 stop13h 15mAir Canada
mié. 11/511:30 amYXE - ORD
1 stop8h 00mAir Canada
Deal found 9/14$497
This Air Canada deal was found by Cheapflights users on 9/13. 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.
dom. 12/288:15 pmORD - YXE
1 stop14h 20mAir Canada
lun. 1/56:00 amYXE - ORD
1 stop7h 01mAir Canada
Deal found 9/13$663

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 septiembre 15, 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

mié. 10/8

7:10 am-9:36 pm

1 stop15h 26m

Regina

mié. 10/15

11:25 am-7:24 pm

1 stop6h 59m

$237

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

jue. 10/30

6:28 pm-9:39 am

1 stop16h 11m

Regina

mar. 11/4

5:00 am-12:05 pm

1 stop7h 05m

$248

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

jue. 11/6

6:28 pm-10:39 am

1 stop16h 11m

Regina

mar. 11/11

10:45 am-8:58 pm

1 stop10h 13m

$251

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

vie. 12/12

8:15 pm-10:39 am

1 stop14h 24m

Regina

jue. 12/18

10:53 am-11:59 pm

1 stop13h 06m

$251

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

jue. 10/30

2:20 pm-10:45 am

1 stop21h 25m

Regina

mar. 11/4

4:25 pm-6:25 am

2 stops14h 00m

$275

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

mié. 10/15

9:55 am-11:57 pm

1 stop15h 02m

Saskatoon

vie. 10/17

7:40 pm-1:14 pm

1 stop16h 34m

$283

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

jue. 10/30

12:50 pm-9:39 am

2 stops21h 49m

Regina

mar. 11/4

5:00 am-1:01 pm

1 stop8h 01m

$286

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

mié. 10/29

7:43 pm-12:49 am

3 stops30h 06m

Saskatoon

mié. 11/5

4:45 pm-6:20 pm

3 stops25h 35m

$364

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

vie. 12/12

8:30 pm-1:56 am

3 stops29h 26m

Regina

jue. 12/18

11:45 am-7:08 pm

1 stop7h 23m

$381

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

mié. 10/29

9:20 pm-9:35 am

1 stop13h 15m

Saskatoon

mié. 11/5

5:05 am-10:50 pm

2 stops17h 45m

$428

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 16 results
1
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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 septiembre 15, 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.

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 septiembre 15, 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
8.0
Very good
7,954 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Crew

8.5

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
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Crew

8.5

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
3,091 reviews
Delta
8.0
Very good
7,954 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Crew

8.5

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.

  • How long is the flight from Chicago to Saskatchewan?

    Departing from Chicago to Saskatchewan will take you 15h 02m. There are 1124 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 - 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, 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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$284Average$380FlexibilityNo cancel feeOn-time69%
WestJetCheapest$289Average$385FlexibilityNo cancel feeOn-time60%
DeltaCheapest$327Average$565FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$365Average$567FlexibilityNo cancel feeOn-time67%

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