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Cheap flights from Saskatchewan to Chicago from C$ 254

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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
29 Jun — 6 Jul1
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 30 May 2026.

Thu 17/97:00 a.m.
YXE
-
ORD
1 stop8h 40m
WestJet
Mon 21/95:30 p.m.
ORD
-
YXE
1 stop6h 40m
WestJet
Deal found 29/5C$ 457
Sat 5/97:00 a.m.
YXE
-
ORD
1 stop8h 40m
WestJet
Fri 11/95:30 p.m.
ORD
-
YXE
1 stop8h 30m
WestJet
Deal found 28/5C$ 462
Tue 27/109:45 a.m.
YQR
-
ORD
1 stop13h 12m
United Airlines
Wed 28/107:15 a.m.
ORD
-
YQR
1 stop15h 26m
United Airlines
Deal found 27/5C$ 495
Tue 27/1010:30 a.m.
YXE
-
ORD
1 stop8h 05m
Air Canada
Wed 28/108:00 a.m.
ORD
-
YXE
1 stop6h 46m
Air Canada
Deal found 28/5C$ 506
Thu 1/107:00 a.m.
YQR
-
ORD
1 stop8h 40m
WestJet
Mon 5/105:30 p.m.
ORD
-
YQR
1 stop6h 50m
WestJet
Deal found 25/5C$ 516
Tue 15/96:00 a.m.
YXE
-
ORD
1 stop6h 23m
Air Canada
Sat 19/93:45 p.m.
ORD
-
YXE
1 stop8h 31m
Air Canada
Deal found 26/5C$ 534
Tue 27/105:00 a.m.
YQR
-
ORD
2 stops14h 10m
Air Canada
Wed 28/108:00 a.m.
ORD
-
YQR
1 stop15h 19m
Air Canada
Deal found 28/5C$ 566
Fri 21/87:00 a.m.
YXE
-
ORD
1 stop8h 40m
WestJet
Mon 31/85:30 p.m.
ORD
-
YXE
1 stop8h 30m
WestJet
Deal found 29/5C$ 572
Tue 15/98:50 a.m.
YXE
-
ORD
1 stop6h 50m
Delta
Sat 19/98:27 a.m.
ORD
-
YXE
2 stops13h 48m
Delta
Deal found 27/5C$ 588
Sat 17/107:00 a.m.
YXE
-
MDW
2 stops10h 37m
Delta
Tue 20/105:35 p.m.
MDW
-
YXE
1 stop5h 00m
Delta
Deal found 27/5C$ 596
Thu 22/1010:45 a.m.
YQR
-
MDW
2 stops10h 00m
Delta
Sat 24/1012:30 p.m.
MDW
-
YQR
1 stop5h 50m
Delta
Deal found 27/5C$ 600
Thu 11/68:05 p.m.
YXE
-
ORD
1 stop11h 55m
Air Canada
Fri 3/75:35 p.m.
ORD
-
YXE
1 stop7h 04m
Air Canada
Deal found 28/5C$ 612

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 30 May 2026.

Round-trip from

C$ 457

One-way from

C$ 254
WestJet
  • WestJet
  • 17/9-21/9
  • 2 total stops
  • 15h 20m total
  • Saskatchewan to Chicago
Search Deals
WestJet
  • WestJet
  • 11/10
  • 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 30 May 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

Tue 27/10

9:45 a.m.-11:57 p.m.

1 stop13h 12m

Chicago O'Hare Intl

Wed 28/10

7:15 a.m.-9:41 p.m.

1 stop15h 26m

C$ 495

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 27/10

10:30 a.m.-7:35 p.m.

1 stop8h 05m

Chicago O'Hare Intl

Wed 28/10

8:00 a.m.-1:46 p.m.

1 stop6h 46m

C$ 506

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 17/9

3:30 p.m.-4:40 p.m.

2 stops24h 10m

Chicago O'Hare Intl

Mon 21/9

5:30 p.m.-3:30 p.m.

2 stops23h 00m

C$ 508

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 1/10

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

1 stop7h 05m

Chicago O'Hare Intl

Mon 5/10

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

2 stops18h 45m

C$ 570

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 15/9

6:00 a.m.-7:48 p.m.

1 stop12h 48m

Chicago O'Hare Intl

Sat 19/9

3:45 p.m.-11:16 p.m.

1 stop8h 31m

C$ 584

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 15/9

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

1 stop6h 50m

Chicago O'Hare Intl

Sat 19/9

8:27 a.m.-9:15 p.m.

2 stops13h 48m

C$ 588

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sat 17/10

7:00 a.m.-6:37 p.m.

2 stops10h 37m

Chicago Midway

Tue 20/10

10:35 a.m.-9:35 p.m.

2 stops12h 00m

C$ 596

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 22/10

10:45 a.m.-9:45 p.m.

2 stops10h 00m

Chicago Midway

Sat 24/10

12:30 p.m.-5:20 p.m.

1 stop5h 50m

C$ 600

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 27/10

7:10 a.m.-6:32 p.m.

2 stops10h 22m

Chicago O'Hare Intl

Wed 28/10

7:40 p.m.-1:38 p.m.

1 stop18h 58m

C$ 636

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 14/8

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

1 stop6h 50m

Chicago O'Hare Intl

Wed 19/8

5:30 p.m.-2:45 p.m.

2 stops22h 15m

C$ 650

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/5

Showing 1-10 of 55 resultsSorted by cheapest first
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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

What is the cheapest month to book a flight from Saskatchewan to Chicago?

Currently, February is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 141). Flying from Saskatchewan to Chicago in September is currently the most expensive (average of C$ 370). 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.

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 05m. 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 Regina - Chicago O'Hare Intl. You may also consider Saskatoon - Chicago O'Hare Intl 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.

  • What is the cheapest month to book a flight from Saskatchewan to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 141). Flying from Saskatchewan to Chicago in September is currently the most expensive (average of C$ 370). 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

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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
Toronto Island to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Vancouver Intl to Midway flights
Ottawa to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Calgary to Midway flights
Pearson Intl to St. Louis flights
Edmonton to O'Hare Intl flights
Halifax to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Québec City to O'Hare Intl flights
Ottawa to Midway flights
Edmonton to Midway flights
Hamilton to O'Hare Intl flights
Halifax to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
Québec City to Midway flights
Calgary to St. Louis flights
Saskatoon to O'Hare Intl flights
Vancouver Intl to St. Louis flights
Edmonton to St. Louis flights
Victoria to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Regina to O'Hare Intl flights
Pearson Intl to Moline flights
Victoria to Midway flights
Saskatoon to Midway flights
Nanaimo to O'Hare Intl flights
St. John's to O'Hare Intl flights
Pearson Intl to Peoria flights
London to O'Hare Intl flights
Québec City to St. Louis flights
St John to O'Hare Intl flights
Halifax to St. Louis flights
Comox to O'Hare Intl flights
Moncton to O'Hare Intl flights
Victoria to St. Louis flights
Charlottetown to St. Louis flights
Ottawa to St. Louis flights
Pearson Intl to Champaign flights
Vancouver Intl to Peoria flights
Kelowna to Midway flights

Top airline flying from Saskatchewan to Chicago

Discover the top airline 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 30 May 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 175AverageC$ 506FlexibilityNo cancel feeOn-time60%
Search WestJet 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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