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Cheap flights from Saskatchewan to Chicago from C$ 170

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 17/5. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
25 Mar — 1 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Saskatchewan to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Saskatchewan to Chicago
Explore the most affordable flight options available from Saskatchewan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 23 February 2026.

Fri 1/58:50 a.m.
YXE
-
ORD
1 stop6h 50m
WestJet
Sun 10/55:30 p.m.
ORD
-
YXE
1 stop6h 40m
WestJet
Deal found 22/2C$ 279
Thu 21/53:30 p.m.
YXE
-
ORD
2 stops24h 10m
WestJet
Sun 24/55:30 p.m.
ORD
-
YXE
1 stop6h 40m
WestJet
Deal found 20/2C$ 319
Sat 25/43:25 p.m.
YQR
-
ORD
1 stop24h 15m
WestJet
Thu 14/55:30 p.m.
ORD
-
YQR
1 stop8h 40m
WestJet
Deal found 22/2C$ 367
Fri 5/67:00 a.m.
YQR
-
ORD
1 stop8h 40m
WestJet
Sun 7/65:30 p.m.
ORD
-
YQR
1 stop8h 40m
WestJet
Deal found 22/2C$ 432
Sun 3/58:50 a.m.
YXE
-
ORD
1 stop6h 50m
Delta
Tue 12/52:00 p.m.
ORD
-
YXE
2 stops12h 00m
Delta
Deal found 20/2C$ 435
Fri 1/57:00 a.m.
YXE
-
ORD
2 stops10h 52m
Delta
Sun 10/52:00 p.m.
ORD
-
YXE
2 stops10h 10m
Delta
Deal found 22/2C$ 443
Thu 16/47:10 a.m.
YXE
-
ORD
1 stop27h 50m
Multiple Airlines
Sat 18/48:58 p.m.
ORD
-
YXE
1 stop27h 20m
Multiple Airlines
Deal found 19/2C$ 477
Sat 25/410:40 a.m.
YQR
-
MDW
1 stop6h 56m
Delta
Thu 14/51:22 p.m.
MDW
-
YQR
2 stops12h 48m
Delta
Deal found 22/2C$ 495
Thu 16/48:45 p.m.
YXE
-
MDW
2 stops17h 35m
Multiple Airlines
Sat 18/412:35 p.m.
MDW
-
YXE
1 stop12h 55m
Multiple Airlines
Deal found 19/2C$ 514
Tue 14/47:10 a.m.
YXE
-
MDW
1 stop5h 22m
Delta
Sat 18/42:12 p.m.
MDW
-
YXE
2 stops11h 36m
Delta
Deal found 19/2C$ 516
Tue 14/47:10 a.m.
YXE
-
ORD
1 stop7h 00m
Delta
Sat 18/412:14 p.m.
ORD
-
YXE
2 stops13h 34m
Delta
Deal found 19/2C$ 516
Tue 31/311:35 a.m.
YQR
-
MDW
1 stop6h 05m
Delta
Wed 8/49:30 a.m.
MDW
-
YQR
1 stop9h 51m
Delta
Deal found 20/2C$ 531

Find flight deals from Saskatchewan to Chicago

Keep the following information in mind while searching for Saskatchewan to Chicago flight deals. Data was last updated 23 February 2026.

Round-trip from

C$ 279

One-way from

C$ 170

Popular in

February

Cheapest in

April

Average price

C$ 1,040
WestJet
  • WestJet
  • 1/5-10/5
  • 2 total stops
  • 13h 30m total
  • Saskatchewan to Chicago
Search Deals
WestJet
  • WestJet
  • 17/5
  • 1 total stop
  • 6h 50m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 26% potential increase in price (C$ 323 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 54 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Saskatchewan to Chicago 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 629,999 searches. Data last updated 23 February 2026.
Use the filters below to find and compare flights from Saskatchewan to Chicago that are best for you.

Fly from

Saskatchewan

Fly to

Chicago

Route

Depart

Return

Price

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 5/6

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Sun 7/6

5:30 p.m.-1:10 a.m.

1 stop8h 40m

C$ 432

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sun 3/5

8:50 a.m.-4:40 p.m.

1 stop6h 50m

Chicago O'Hare Intl

Tue 12/5

2:00 p.m.-1:00 a.m.

2 stops12h 00m

C$ 435

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 1/5

7:00 a.m.-6:52 p.m.

2 stops10h 52m

Chicago O'Hare Intl

Sun 10/5

2:00 p.m.-11:10 p.m.

2 stops10h 10m

C$ 443

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 25/4

3:25 p.m.-4:40 p.m.

1 stop24h 15m

Chicago O'Hare Intl

Thu 14/5

5:30 p.m.-11:15 a.m.

2 stops18h 45m

C$ 455

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 16/4

7:10 a.m.-12:00 p.m.

1 stop27h 50m

Chicago O'Hare Intl

Sat 18/4

8:58 p.m.-11:18 p.m.

1 stop27h 20m

C$ 477

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sat 25/4

10:40 a.m.-6:36 p.m.

1 stop6h 56m

Chicago Midway

Thu 14/5

1:22 p.m.-1:10 a.m.

2 stops12h 48m

C$ 495

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Thu 16/4

8:45 p.m.-3:20 p.m.

2 stops17h 35m

Chicago Midway

Sat 18/4

12:35 p.m.-12:30 a.m.

1 stop12h 55m

C$ 514

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Tue 14/4

7:10 a.m.-1:32 p.m.

1 stop5h 22m

Chicago Midway

Sat 18/4

2:12 p.m.-12:48 a.m.

2 stops11h 36m

C$ 516

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Tue 7/4

7:10 a.m.-1:24 p.m.

1 stop5h 14m

Chicago Midway

Tue 14/4

9:29 a.m.-1:37 p.m.

1 stop5h 08m

C$ 516

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 14/4

7:10 a.m.-3:10 p.m.

1 stop7h 00m

Chicago O'Hare Intl

Sat 18/4

12:14 p.m.-12:48 a.m.

2 stops13h 34m

C$ 516

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/2

Showing 1-10 of 59 results
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Best time to book a flight from Saskatchewan to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Saskatchewan 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 Saskatchewan to Chicago

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

Related info for your journey

Find useful and relevant information for your journey from Saskatchewan to Chicago. 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 Saskatchewan to Chicago?

    For as low as C$ 435, WestJet can have you in Chicago from Saskatchewan in 6h 50m. The distance from Saskatchewan to Chicago is about 1809 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the most popular routes from Saskatchewan to Chicago?

    The most popular route from Saskatchewan to Chicago is Saskatoon - Chicago O'Hare Intl. You may also consider Regina - Chicago O'Hare Intl or Regina - Chicago Midway.

  • Can I find deals for flights from Saskatchewan to Chicago that include hotel bookings?

    Yes. In addition to deals on Saskatchewan to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Saskatchewan to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Saskatchewan to Chicago.

  • Can I find deals for business class flights from Saskatchewan to Chicago?

    Yes. Cheapflights offers flight deals from Saskatchewan to Chicago 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

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Alternative routes for Saskatchewan to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Toronto Island to Midway flights
Calgary to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Toronto Island to O'Hare Intl flights
Vancouver Intl to Midway flights
Calgary to Midway flights
Edmonton to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Halifax to O'Hare Intl flights
Edmonton to Midway flights
Pearson Intl to St. Louis flights
Winnipeg to O'Hare Intl flights
Vancouver Intl to St. Louis flights
Ottawa to Midway flights
Halifax to Midway flights
Pierre Elliott Trudeau Intl to St. Louis flights
Hamilton to O'Hare Intl flights
Québec City to O'Hare Intl flights
Halifax to St. Louis flights
Kelowna to O'Hare Intl flights
Calgary to St. Louis flights
Québec City to Midway flights
Victoria to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Edmonton to St. Louis flights
London to O'Hare Intl flights
Regina to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights
Victoria to Midway flights
Pearson Intl to Bloomington flights
Québec City to St. Louis flights
Vancouver Intl to Peoria flights
Saskatoon to Midway flights
St. John's to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
Fort McMurray to O'Hare Intl flights
Sudbury to O'Hare Intl flights
Charlottetown to St. Louis flights
Moncton to O'Hare Intl flights
Ottawa to St. Louis flights
St John to O'Hare Intl flights
Saskatoon to St. Louis flights

Top 3 airlines flying from Saskatchewan to Chicago

Discover the top 3 airlines that operate flights from Saskatchewan to Chicago. 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 629,999 searches. Data last updated 23 February 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 173AverageC$ 429FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 308AverageC$ 506FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 407AverageC$ 958FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Saskatchewan to Chicago?

When you search for this flight from Saskatchewan to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Saskatchewan to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Saskatchewan.

Can Cheapflights find flights from Saskatchewan to Chicago with no change fees?

Need flexible booking options for your flight to Chicago from Saskatchewan? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Saskatchewan to Chicago become cheaper?

Not ready to book yet? You can track prices for flights from Saskatchewan to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.

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