Find flights
When to book
FAQs

Cheap flights from Saskatchewan to Chicago from C$ 213

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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
11 May — 18 May1
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 11 April 2026.

Mon 27/47:00 a.m.
YXE
-
ORD
1 stop8h 40m
WestJet
Fri 8/55:30 p.m.
ORD
-
YXE
1 stop8h 30m
WestJet
Deal found 8/4C$ 379
Wed 20/57:00 a.m.
YXE
-
ORD
1 stop8h 40m
WestJet
Fri 29/55:30 p.m.
ORD
-
YXE
1 stop8h 30m
WestJet
Deal found 8/4C$ 400
Thu 21/56:00 a.m.
YXE
-
ORD
1 stop9h 40m
WestJet
Fri 29/55:30 p.m.
ORD
-
YXE
1 stop6h 40m
WestJet
Deal found 8/4C$ 413
Sun 26/43:30 p.m.
YXE
-
ORD
2 stops24h 10m
WestJet
Fri 1/55:30 p.m.
ORD
-
YXE
1 stop8h 30m
WestJet
Deal found 8/4C$ 419
Thu 30/46:00 a.m.
YXE
-
ORD
1 stop9h 40m
WestJet
Fri 8/55:30 p.m.
ORD
-
YXE
1 stop6h 40m
WestJet
Deal found 8/4C$ 420
Sun 26/48:00 a.m.
YXE
-
ORD
1 stop7h 40m
WestJet
Sun 3/55:30 p.m.
ORD
-
YXE
1 stop6h 40m
WestJet
Deal found 8/4C$ 427
Sat 23/57:00 a.m.
YXE
-
ORD
1 stop8h 40m
WestJet
Wed 27/55:30 p.m.
ORD
-
YXE
1 stop6h 40m
WestJet
Deal found 8/4C$ 434
Sat 25/48:45 p.m.
YXE
-
ORD
1 stop18h 55m
WestJet
Fri 1/55:30 p.m.
ORD
-
YXE
1 stop8h 30m
WestJet
Deal found 8/4C$ 443
Thu 7/58:50 a.m.
YXE
-
ORD
1 stop6h 50m
Multiple Airlines
Thu 14/58:00 a.m.
ORD
-
YXE
1 stop14h 35m
Multiple Airlines
Deal found 8/4C$ 454
Mon 18/58:50 a.m.
YXE
-
ORD
1 stop6h 50m
Multiple Airlines
Mon 1/68:06 p.m.
ORD
-
YXE
1 stop26h 29m
Multiple Airlines
Deal found 8/4C$ 466
Mon 27/47:00 a.m.
YXE
-
ORD
1 stop8h 40m
Multiple Airlines
Mon 4/57:50 a.m.
ORD
-
YXE
2 stops18h 10m
Multiple Airlines
Deal found 8/4C$ 467
Sat 9/55:45 a.m.
YQR
-
ORD
1 stop8h 10m
Air Canada
Tue 12/58:45 a.m.
ORD
-
YQR
2 stops11h 22m
Air Canada
Deal found 6/4C$ 483

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 11 April 2026.

Round-trip from

C$ 379

One-way from

C$ 213
WestJet
  • WestJet
  • 27/4-3/5
  • 2 total stops
  • 15h 20m total
  • Saskatchewan to Chicago
Search Deals
WestJet
  • WestJet
  • 3/5
  • 1 total stop
  • 6h 50m total
  • Saskatchewan to Chicago
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 11 April 2026.
Use the filters below to find and compare flights from Saskatchewan to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 2/5

9:45 a.m.-9:23 p.m.

1 stop10h 38m

Chicago O'Hare Intl

Wed 6/5

1:43 p.m.-9:30 p.m.

1 stop8h 47m

C$ 487

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 9/5

5:45 a.m.-8:08 p.m.

2 stops13h 23m

Chicago O'Hare Intl

Tue 12/5

8:45 a.m.-7:07 p.m.

2 stops11h 22m

C$ 487

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 29/5

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

1 stop8h 40m

Chicago O'Hare Intl

Tue 2/6

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

2 stops10h 10m

C$ 506

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 24/5

8:35 a.m.-4:40 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Sun 31/5

8:06 p.m.-5:20 p.m.

1 stop22h 14m

C$ 512

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Fri 22/5

7:00 a.m.-6:33 p.m.

2 stops10h 33m

Chicago Midway

Wed 27/5

1:22 p.m.-11:10 p.m.

2 stops10h 48m

C$ 516

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Tue 19/5

7:00 a.m.-6:33 p.m.

2 stops10h 33m

Chicago Midway

Wed 27/5

1:22 p.m.-11:10 p.m.

2 stops10h 48m

C$ 516

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sat 16/5

6:00 a.m.-6:33 p.m.

2 stops11h 33m

Chicago Midway

Sat 30/5

1:22 p.m.-11:10 p.m.

2 stops10h 48m

C$ 516

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sat 16/5

7:00 a.m.-6:33 p.m.

2 stops10h 33m

Chicago Midway

Tue 2/6

1:22 p.m.-11:10 p.m.

2 stops10h 48m

C$ 516

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sat 16/5

6:00 a.m.-6:33 p.m.

2 stops11h 33m

Chicago Midway

Fri 29/5

1:22 p.m.-11:10 p.m.

2 stops10h 48m

C$ 516

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sat 16/5

7:00 a.m.-8:14 p.m.

2 stops12h 14m

Chicago O'Hare Intl

Wed 27/5

5:30 p.m.-11:10 p.m.

1 stop6h 40m

C$ 516

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/4

Showing 1-10 of 53 resultsSorted by cheapest first
1
2
3
...
6

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$ 506, United Airlines can have you in Chicago from Saskatchewan in 8h 40m. 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 Saskatoon - Chicago Midway or Regina - Chicago O'Hare Intl.

  • 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

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 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
Pearson Intl to Midway flights
Toronto Island to Midway flights
Toronto Island to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Calgary to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Vancouver Intl to Midway flights
Edmonton to O'Hare Intl flights
Pearson Intl to St. Louis flights
Halifax to O'Hare Intl flights
Ottawa to Midway flights
Winnipeg to O'Hare Intl flights
Edmonton to Midway flights
Québec City to O'Hare Intl flights
Vancouver Intl to St. Louis flights
Hamilton to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Calgary to Midway flights
Halifax to Midway flights
Saskatoon to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights
Québec City to Midway flights
Calgary to St. Louis flights
Saskatoon to Midway flights
Victoria to O'Hare Intl flights
Victoria to Midway flights
Pearson Intl to Peoria flights
Kelowna to O'Hare Intl flights
Regina to O'Hare Intl flights
Moncton to O'Hare Intl flights
St John to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Pearson Intl to Champaign flights
Edmonton to St. Louis flights
Ottawa to St. Louis flights
Halifax to St. Louis flights
St. John's to O'Hare Intl flights
Deer Lake to O'Hare Intl flights
Québec City to St. Louis flights
Victoria to St. Louis flights
Sudbury to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
Comox to O'Hare Intl flights
Fort McMurray 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 11 April 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 175AverageC$ 425FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 411AverageC$ 968FlexibilityNo 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.

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.