HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Saskatchewan

$121+ 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 3/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Saskatchewan with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$278
(Kiwi.com)

One-way from

$132
(Kiwi.com)
Provider with most accurate pricing for Chicago (CHI)-Regina flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Regina flights.
Search Deals
From Chicago (CHI) to Saskatchewan
Search Deals
One-way flight from Chicago (CHI) to Saskatchewan
Search Deals

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 febrero 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/67:00 amORD - YQR
1 stop10h 36mMultiple Airlines
dom. 4/1310:45 amYQR - ORD
1 stop8h 34mMultiple Airlines
Deal found 2/20$278
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
dom. 4/67:00 amORD - YXE
1 stop7h 50mMultiple Airlines
dom. 4/137:10 amYXE - ORD
1 stop12h 09mMultiple Airlines
Deal found 2/19$292
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/64:45 pmORD - YXE
1 stop9h 03mWestJet
dom. 4/133:35 pmYXE - ORD
2 stops23h 21mWestJet
Deal found 2/19$330
This Flightnetwork deal was found by Cheapflights users on 2/20. 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.
dom. 4/64:45 pmORD - YQR
1 stop9h 11mWestJet
dom. 4/135:10 pmYQR - ORD
2 stops21h 46mWestJet
Deal found 2/20$334
This Trip.com deal was found by Cheapflights users on 2/18. 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.
mié. 3/1911:15 amMDW - YXE
1 stop13h 59mMultiple Airlines
mié. 3/264:45 amYXE - MDW
1 stop10h 55mMultiple Airlines
Deal found 2/18$336
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/57:50 amORD - YQR
1 stop9h 46mDelta
sáb. 4/1210:45 amYQR - ORD
1 stop8h 23mDelta
Deal found 2/19$461
This Air Canada deal was found by Cheapflights users on 2/20. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/249:14 pmORD - YXE
1 stop14h 37mAir Canada
mar. 7/297:30 pmYXE - ORD
1 stop12h 39mAir Canada
Deal found 2/20$462
This Delta deal was found by Cheapflights users on 2/20. 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.
vie. 6/275:20 pmORD - YXE
1 stop5h 05mDelta
lun. 6/303:15 pmYXE - ORD
1 stop5h 39mDelta
Deal found 2/20$476
This Justfly.com deal was found by Cheapflights users on 2/18. 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.
jue. 4/2410:20 amMDW - YXE
2 stops14h 54mWestJet
sáb. 5/105:40 amYXE - MDW
2 stops11h 24mWestJet
Deal found 2/18$581
This Delta deal was found by Cheapflights users on 2/20. 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.
dom. 4/61:15 pmMDW - YXE
2 stops12h 33mDelta
dom. 4/137:10 amYXE - MDW
1 stop6h 07mDelta
Deal found 2/20$623

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 febrero 20, 2025.

Fly from

Chicago

Fly to

Saskatchewan

Route

Depart

Return

Price

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

dom. 4/6

7:00 am-4:36 pm

1 stop10h 36m

Regina

dom. 4/13

10:45 am-8:19 pm

1 stop8h 34m

$278

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

dom. 4/6

7:00 am-1:50 pm

1 stop7h 50m

Saskatoon

dom. 4/13

7:10 am-8:19 pm

1 stop12h 09m

$292

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

dom. 4/6

4:45 pm-12:48 am

1 stop9h 03m

Saskatoon

dom. 4/13

3:35 pm-3:56 pm

2 stops23h 21m

$330

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

dom. 4/6

4:45 pm-12:56 am

1 stop9h 11m

Regina

dom. 4/13

5:10 pm-3:56 pm

2 stops21h 46m

$334

ChicagoSaskatoon

MDW - YXE

MDWYXE

Chicago Midway

mié. 3/19

11:15 am-12:14 am

1 stop13h 59m

Saskatoon

mié. 3/26

4:45 am-4:40 pm

1 stop10h 55m

$336

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

sáb. 4/5

7:50 am-4:36 pm

1 stop9h 46m

Regina

sáb. 4/12

10:45 am-8:08 pm

1 stop8h 23m

$461

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

jue. 7/24

9:14 pm-10:51 am

1 stop14h 37m

Saskatoon

mar. 7/29

7:30 pm-9:09 am

1 stop12h 39m

$462

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

vie. 6/27

5:20 pm-9:25 pm

1 stop5h 05m

Saskatoon

lun. 6/30

3:15 pm-9:54 pm

1 stop5h 39m

$476

ChicagoSaskatoon

MDW - YXE

MDWYXE

Chicago Midway

jue. 4/24

10:20 am-12:14 am

2 stops14h 54m

Saskatoon

sáb. 5/10

5:40 am-6:04 pm

2 stops11h 24m

$581

ChicagoSaskatoon

MDW - YXE

MDWYXE

Chicago Midway

dom. 4/6

1:15 pm-12:48 am

2 stops12h 33m

Saskatoon

dom. 4/13

7:10 am-2:17 pm

1 stop6h 07m

$623

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 16 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 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 febrero 20, 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 febrero 20, 2025.
Peruse reviews from past customers who have flown with Delta, 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
8,220 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

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

Delta
8.0
Very good
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

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

WestJet
7.2
Good
2,801 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

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

Air Canada
7.0
Good
8,748 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Comfort

8.0

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

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 Midway - Saskatoon or Chicago O'Hare Intl - Regina 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 $398). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Saskatchewan

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Vancouver Intl flights
O'Hare Intl to Calgary flights
O'Hare Intl to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Pearson Intl flights
Midway to Pierre Elliott Trudeau Intl flights
Midway to Vancouver Intl flights
Midway to Calgary flights
Midway to Toronto Island flights
Midway to Pearson Intl flights
O'Hare Intl to Abbotsford flights
O'Hare Intl to Toronto Island flights
O'Hare Intl to Québec City flights
St. Louis to Vancouver Intl flights
O'Hare Intl to Ottawa flights
O'Hare Intl to Edmonton flights
St. Louis to Pearson Intl flights
St. Louis to Calgary flights
O'Hare Intl to Winnipeg flights
O'Hare Intl to Halifax flights
St. Louis to Pierre Elliott Trudeau Intl flights
Midway to Québec City flights
O'Hare Intl to St. John's flights
Midway to Edmonton flights
Midway to Ottawa flights
Midway to Halifax flights
O'Hare Intl to Hamilton flights
Midway to St. John's flights
St. Louis to St. John's flights
O'Hare Intl to Saskatoon flights
O'Hare Intl to Victoria flights
St. Louis to Québec City flights
Midway to Saskatoon flights
Midway to Winnipeg flights
Midway to Victoria flights
St. Louis to Halifax flights
O'Hare Intl to Charlottetown flights
O'Hare Intl to Kelowna flights
St. Louis to Winnipeg flights
O'Hare Intl to Sydney flights
O'Hare Intl to Deer Lake flights
Moline to Calgary flights
Peoria to Vancouver Intl flights
St. Louis to Saskatoon flights
Moline to Pearson Intl flights
St. Louis to Edmonton flights
O'Hare Intl to Fredericton flights
O'Hare Intl to London flights
Midway to Kelowna flights
St. Louis to Ottawa flights

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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$282Average$509FlexibilityNo cancel feeOn-time67%
WestJetCheapest$366Average$608FlexibilityNo cancel feeOn-time60%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.