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Cheap flights from Saskatchewan to Chicago from C$ 215

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 25/2. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
11 Mar — 18 Mar1
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 9 February 2026.

Fri 27/26:10 a.m.
YQR
-
ORD
1 stop7h 25m
WestJet
Thu 30/45:30 p.m.
ORD
-
YQR
1 stop8h 40m
WestJet
Deal found 8/2C$ 383
Fri 24/45:10 a.m.
YQR
-
ORD
1 stop7h 25m
WestJet
Sun 26/45:30 p.m.
ORD
-
YQR
1 stop18h 20m
WestJet
Deal found 8/2C$ 392
Tue 14/45:00 a.m.
YXE
-
ORD
1 stop7h 05m
Air Canada
Sat 18/47:55 a.m.
ORD
-
YXE
1 stop6h 36m
Air Canada
Deal found 8/2C$ 406
Wed 25/35:00 a.m.
YQR
-
ORD
1 stop7h 01m
Air Canada
Wed 1/46:40 p.m.
ORD
-
YQR
1 stop15h 52m
Air Canada
Deal found 8/2C$ 451
Tue 14/45:00 a.m.
YXE
-
ORD
1 stop7h 05m
Air Canada
Fri 17/46:40 p.m.
ORD
-
YXE
1 stop15h 46m
Air Canada
Deal found 6/2C$ 481
Wed 25/35:00 a.m.
YQR
-
ORD
1 stop7h 01m
Air Canada
Sun 29/38:20 p.m.
ORD
-
YQR
1 stop14h 12m
Air Canada
Deal found 8/2C$ 486
Sun 29/35:00 a.m.
YQR
-
ORD
1 stop7h 05m
United Airlines
Thu 2/42:35 p.m.
ORD
-
YQR
1 stop7h 55m
United Airlines
Deal found 8/2C$ 497
Fri 10/77:00 a.m.
YXE
-
ORD
1 stop8h 43m
WestJet
Tue 14/75:30 p.m.
ORD
-
YXE
1 stop8h 23m
WestJet
Deal found 7/2C$ 500
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 8/2C$ 504
Tue 24/37:10 a.m.
YXE
-
ORD
1 stop7h 09m
Delta
Tue 31/36:15 a.m.
ORD
-
YXE
1 stop8h 22m
Delta
Deal found 6/2C$ 504
Mon 2/35:00 a.m.
YQR
-
ORD
1 stop14h 45m
Air Canada
Tue 3/38:40 p.m.
ORD
-
YQR
1 stop13h 59m
Air Canada
Deal found 8/2C$ 512
Sat 7/39:45 p.m.
YQR
-
MDW
2 stops16h 35m
Multiple Airlines
Sat 14/312:45 p.m.
MDW
-
YQR
1 stop12h 30m
Multiple Airlines
Deal found 6/2C$ 512

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 9 February 2026.

Round-trip from

C$ 383

One-way from

C$ 215

Popular in

February

Cheapest in

April

Average price

C$ 1,035
WestJet
  • WestJet
  • 27/2-30/4
  • 2 total stops
  • 16h 05m total
  • Saskatchewan to Chicago
Search Deals
25/2
  • 25/2
  • 3 total stops
  • 31h 49m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 26% potential increase in price (C$ 318 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 52 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 9 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 27/2

6:10 a.m.-1:35 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Thu 30/4

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

1 stop8h 40m

C$ 383

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 24/4

5:10 a.m.-1:35 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Sun 26/4

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

2 stops18h 45m

C$ 395

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 14/4

5:00 a.m.-1:05 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Sat 18/4

7:55 a.m.-1:31 p.m.

1 stop6h 36m

C$ 406

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 25/3

5:00 a.m.-1:01 p.m.

1 stop7h 01m

Chicago O'Hare Intl

Sun 29/3

8:20 p.m.-9:32 a.m.

1 stop14h 12m

C$ 486

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 29/3

5:00 a.m.-1:05 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Wed 1/4

6:40 p.m.-9:32 a.m.

1 stop15h 52m

C$ 486

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 26/3

5:00 a.m.-1:01 p.m.

1 stop7h 01m

Chicago O'Hare Intl

Mon 30/3

8:20 p.m.-9:32 a.m.

1 stop14h 12m

C$ 486

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 14/4

5:00 a.m.-1:05 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Fri 17/4

12:50 p.m.-9:26 a.m.

2 stops21h 36m

C$ 486

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 29/3

5:00 a.m.-1:05 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Thu 2/4

2:35 p.m.-9:30 p.m.

1 stop7h 55m

C$ 497

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Tue 24/3

7:10 a.m.-1:25 p.m.

1 stop5h 15m

Chicago Midway

Tue 31/3

9:30 a.m.-1:37 p.m.

1 stop5h 07m

C$ 504

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Tue 14/4

7:10 a.m.-10:28 p.m.

2 stops14h 18m

Chicago Midway

Sat 18/4

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

2 stops11h 36m

C$ 504

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/2

Showing 1-10 of 46 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
No data available for this route at this time. Please check back soon.

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$ 504, WestJet can have you in Chicago from Saskatchewan in 5h 15m. The distance from Saskatchewan to Chicago is about 1833 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 Midway or Saskatoon - 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
Calgary to O'Hare Intl flights
Pearson Intl to Midway flights
Toronto Island to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Toronto Island to O'Hare Intl flights
Pearson Intl to St. Louis flights
Vancouver Intl to Midway flights
Ottawa to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Vancouver Intl to St. Louis flights
Halifax to O'Hare Intl flights
Calgary to Midway flights
Edmonton to Midway flights
Winnipeg to O'Hare Intl flights
Québec City to O'Hare Intl flights
Halifax to Midway flights
Ottawa to Midway flights
Pierre Elliott Trudeau Intl to St. Louis flights
Saskatoon to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Saskatoon to Midway flights
Victoria to O'Hare Intl flights
Halifax to St. Louis flights
Québec City to Midway flights
Regina to O'Hare Intl flights
Ottawa to St. Louis flights
Region of Waterloo Intl to O'Hare Intl flights
Vancouver Intl to Peoria flights
Moncton to O'Hare Intl flights
Calgary to St. Louis flights
St John to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Québec City to St. Louis flights
London to O'Hare Intl flights
Victoria to Midway flights
Pearson Intl to Peoria flights
Edmonton to St. Louis flights
Kelowna to Midway flights
Fort McMurray to O'Hare Intl flights
Victoria to St. Louis flights
Nanaimo to O'Hare Intl flights
Charlottetown to St. Louis flights
Sudbury to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
Comox to O'Hare Intl flights

Top 2 airlines flying from Saskatchewan to Chicago

Discover the top 2 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 9 February 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 172AverageC$ 418FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 175AverageC$ 1,453FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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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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