HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Saskatchewan

$102+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YXE
Jan 2 — Jan 91
Fri 1/2
Fri 1/9
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

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 December 3, 2025.

This Mytrip deal was found by Cheapflights users on 12/1. 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 12/2411:03 amORD - YXE
3 stops33h 56mMultiple Airlines
Tue 12/308:10 amYXE - ORD
1 stop9h 34mMultiple Airlines
Deal found 12/1$686
This oojo deal was found by Cheapflights users on 12/3. 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.
Mon 12/82:20 pmORD - YQR
2 stops20h 14mWestJet
Fri 12/126:10 amYQR - ORD
1 stop7h 25mWestJet
Deal found 12/3$719
This Air Canada deal was found by Cheapflights users on 12/1. 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.
Wed 12/243:55 pmORD - YXE
1 stop7h 40mAir Canada
Tue 12/3011:30 amYXE - ORD
1 stop8h 15mAir Canada
Deal found 12/1$787
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Tue 12/164:22 pmORD - YXE
2 stops26h 40mMultiple Airlines
Fri 12/196:25 amYXE - ORD
1 stop7h 10mMultiple Airlines
Deal found 12/2$800
This Air Canada deal was found by Cheapflights users on 12/2. 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.
Sat 12/278:30 pmORD - YXE
1 stop14h 05mAir Canada
Mon 1/511:25 amYXE - ORD
1 stop8h 20mAir Canada
Deal found 12/2$831
This United Airlines deal was found by Cheapflights users on 12/3. 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.
Mon 12/812:45 pmORD - YQR
2 stops10h 12mUnited Airlines
Fri 12/1210:53 amYQR - ORD
2 stops26h 15mUnited Airlines
Deal found 12/3$838
This Air Canada deal was found by Cheapflights users on 12/2. 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.
Sun 12/218:30 pmORD - YXE
1 stop14h 05mAir Canada
Sun 1/186:00 amYXE - ORD
1 stop13h 45mAir Canada
Deal found 12/2$861
This Air Canada deal was found by Cheapflights users on 12/1. 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.
Sun 12/218:30 pmORD - YXE
1 stop14h 05mAir Canada
Sat 1/173:25 pmYXE - ORD
2 stops19h 41mAir Canada
Deal found 12/1$869
This Delta deal was found by Cheapflights users on 12/2. 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 12/166:00 amORD - YXE
1 stop8h 38mDelta
Fri 12/196:25 amYXE - ORD
1 stop7h 10mDelta
Deal found 12/2$910
This Air Canada deal was found by Cheapflights users on 12/3. 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.
Sun 12/219:20 pmORD - YXE
1 stop26h 15mAir Canada
Sat 1/106:00 amYXE - ORD
1 stop9h 10mAir Canada
Deal found 12/3$911
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Mon 12/86:00 amORD - YQR
1 stop12h 20mMultiple Airlines
Fri 12/1211:40 amYQR - ORD
2 stops30h 56mMultiple Airlines
Deal found 12/2$927
This FlightHub deal was found by Cheapflights users on 12/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/275:59 pmMDW - YXE
1 stop20h 39mWestJet
Mon 1/58:20 pmYXE - MDW
2 stops14h 07mWestJet
Deal found 12/1$1,041

Find flight deals from Chicago to Saskatchewan

Keep the following information in mind while searching for Chicago to Saskatchewan flight deals. Data was last updated December 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$268
(Kissandfly.com)

One-way from

$102
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$706
Provider with most accurate pricing for Chicago (CHI)-Saskatoon flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Saskatoon flights.
Search Deals
From Chicago (CHI) to Saskatchewan
Search Deals
One-way flight from Chicago (CHI) to Saskatchewan
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($103 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 3, 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

Mon 1/26

2:20 pm-9:08 pm

1 stop6h 48m

Regina

Tue 2/3

5:00 am-1:01 pm

1 stop8h 01m

$268

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 1/16

2:20 pm-12:23 am

1 stop10h 03m

Regina

Fri 1/23

6:10 am-1:35 pm

1 stop7h 25m

$286

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 1/16

2:20 pm-1:56 am

1 stop11h 36m

Regina

Fri 1/23

4:25 pm-4:51 pm

2 stops24h 26m

$333

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 1/20

12:53 pm-10:51 pm

1 stop9h 58m

Regina

Tue 1/27

10:45 am-5:04 pm

1 stop6h 19m

$335

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 1/26

3:35 pm-10:39 am

2 stops19h 04m

Regina

Tue 2/3

5:00 am-8:10 pm

2 stops15h 10m

$369

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 3/5

12:05 pm-1:15 am

2 stops13h 10m

Regina

Sun 3/8

8:45 pm-1:35 pm

1 stop15h 50m

$369

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Fri 1/16

2:20 pm-12:12 am

1 stop9h 52m

Saskatoon

Fri 1/23

9:35 am-4:51 pm

2 stops31h 16m

$373

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 3/5

9:14 pm-10:39 am

1 stop13h 25m

Regina

Sun 3/8

5:00 am-1:01 pm

1 stop7h 01m

$432

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 4/1

12:15 pm-6:21 pm

1 stop7h 06m

Regina

Sun 4/5

11:45 am-7:59 pm

1 stop7h 14m

$436

ChicagoSaskatoon

ORD - YXE

ORDYXE

Chicago O'Hare Intl

Fri 1/16

2:20 pm-8:59 pm

1 stop6h 39m

Saskatoon

Fri 1/23

6:25 am-1:35 pm

1 stop7h 10m

$456

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 32 results
1
2
3
4

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 December 3, 2025.

One of the essential ways to save on airfare from Chicago to Saskatchewan is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 47% on airfare.

How much does it cost to fly round-trip from Chicago to Saskatchewan?

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 3, 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
7.9
Good
8,011 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,011 reviews
Delta
7.9
Good
8,011 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
WestJet
7.2
Good
3,190 reviews
Delta
7.9
Good
8,011 reviews

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 5h 17m. There are 1139 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.

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 Pearson Intl flights
O'Hare Intl to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Calgary flights
Midway to Vancouver Intl flights
Midway to Pierre Elliott Trudeau Intl flights
Midway to Toronto Island flights
Midway to Pearson Intl flights
O'Hare Intl to Toronto Island flights
O'Hare Intl to Abbotsford flights
Midway to Calgary flights
St. Louis to Pearson Intl flights
St. Louis to Vancouver Intl flights
O'Hare Intl to Québec City flights
O'Hare Intl to Ottawa flights
O'Hare Intl to Winnipeg flights
Midway to Québec City flights
St. Louis to Pierre Elliott Trudeau Intl flights
St. Louis to Calgary flights
O'Hare Intl to Halifax flights
O'Hare Intl to Hamilton flights
Midway to Ottawa flights
O'Hare Intl to Saskatoon flights
O'Hare Intl to St. John's flights
St. Louis to Québec City flights
O'Hare Intl to Kelowna flights
St. Louis to Winnipeg flights
O'Hare Intl to Edmonton flights
Peoria to Vancouver Intl flights
Midway to Winnipeg flights
O'Hare Intl to Victoria flights
Midway to Halifax flights
Midway to Edmonton flights
St. Louis to Ottawa flights
St. Louis to Victoria flights
Midway to St. John's flights
Midway to Victoria flights
St. Louis to Edmonton flights
St. Louis to Halifax flights
O'Hare Intl to Sydney flights
O'Hare Intl to London flights
Midway to Saskatoon flights
Bloomington to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Thunder Bay flights
O'Hare Intl to Regina flights
St. Louis to St. John's flights
Evansville to Pierre Elliott Trudeau Intl flights
Midway to Kelowna flights
Springfield to Pearson Intl flights

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 December 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$245Average$649FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$284Average$466FlexibilityNo cancel feeOn-time69%
WestJetCheapest$289Average$385FlexibilityNo cancel feeOn-time60%
DeltaCheapest$327Average$540FlexibilityNo cancel feeOn-timeN/A

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.