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Cheap flights from Saskatchewan to Chicago from C$ 225

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
18 Jun — 25 Jun1
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 19 May 2026.

Tue 9/67:00 a.m.
YQR
-
ORD
1 stop8h 40m
WestJet
Fri 12/65:30 p.m.
ORD
-
YQR
1 stop8h 40m
WestJet
Deal found 16/5C$ 397
Sun 7/68:55 p.m.
YXE
-
ORD
1 stop18h 45m
WestJet
Sat 13/65:30 p.m.
ORD
-
YXE
1 stop6h 40m
WestJet
Deal found 14/5C$ 427
Fri 5/611:50 a.m.
YQR
-
ORD
2 stops27h 50m
WestJet
Sun 7/65:30 p.m.
ORD
-
YQR
1 stop18h 20m
WestJet
Deal found 15/5C$ 489
Mon 17/87:00 a.m.
YXE
-
ORD
1 stop8h 40m
WestJet
Wed 19/85:30 p.m.
ORD
-
YXE
1 stop6h 40m
WestJet
Deal found 17/5C$ 504
Mon 17/88:35 a.m.
YQR
-
ORD
1 stop7h 05m
WestJet
Fri 21/85:30 p.m.
ORD
-
YQR
1 stop8h 40m
WestJet
Deal found 16/5C$ 521
Fri 12/69:45 a.m.
YQR
-
ORD
1 stop13h 59m
United Airlines
Sat 20/67:05 a.m.
ORD
-
YQR
1 stop15h 25m
United Airlines
Deal found 15/5C$ 524
Tue 29/97:00 a.m.
YXE
-
ORD
1 stop8h 40m
Delta
Sat 3/101:35 p.m.
ORD
-
YXE
2 stops10h 35m
Delta
Deal found 18/5C$ 543
Wed 16/912:40 p.m.
YQR
-
ORD
1 stop6h 08m
Air Canada
Sat 19/98:45 a.m.
ORD
-
YQR
2 stops11h 20m
Air Canada
Deal found 17/5C$ 548
Tue 29/97:00 a.m.
YXE
-
MDW
2 stops10h 05m
Delta
Sat 3/101:00 p.m.
MDW
-
YXE
2 stops13h 00m
Delta
Deal found 17/5C$ 550
Sat 12/912:40 p.m.
YQR
-
ORD
1 stop6h 08m
Air Canada
Mon 21/98:40 p.m.
ORD
-
YQR
1 stop13h 30m
Air Canada
Deal found 15/5C$ 570
Sun 7/63:10 p.m.
YXE
-
ORD
1 stop5h 15m
Delta
Sat 13/65:30 p.m.
ORD
-
YXE
1 stop8h 30m
Delta
Deal found 18/5C$ 584
Tue 16/63:10 p.m.
YXE
-
ORD
1 stop5h 15m
Delta
Sat 20/611:15 a.m.
ORD
-
YXE
2 stops14h 20m
Delta
Deal found 18/5C$ 602

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 19 May 2026.

Round-trip from

C$ 397

One-way from

C$ 225
WestJet
  • WestJet
  • 9/6-12/6
  • 2 total stops
  • 17h 20m total
  • Saskatchewan to Chicago
Search Deals
WestJet
  • WestJet
  • 11/10
  • 1 total stop
  • 8h 40m 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 19 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

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sun 7/6

8:55 p.m.-4:40 p.m.

1 stop18h 45m

Chicago O'Hare Intl

Sat 13/6

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

1 stop6h 40m

C$ 427

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 5/6

11:50 a.m.-4:40 p.m.

2 stops27h 50m

Chicago O'Hare Intl

Sun 7/6

5:30 p.m.-10:50 a.m.

1 stop18h 20m

C$ 489

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Mon 17/8

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

1 stop8h 40m

Chicago O'Hare Intl

Wed 19/8

5:30 p.m.-1:00 a.m.

1 stop8h 30m

C$ 504

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 29/9

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

1 stop8h 40m

Chicago O'Hare Intl

Sat 3/10

1:35 p.m.-11:10 p.m.

2 stops10h 35m

C$ 543

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Tue 29/9

7:00 a.m.-6:05 p.m.

2 stops10h 05m

Chicago Midway

Sat 3/10

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

2 stops13h 00m

C$ 550

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sun 7/6

3:10 p.m.-9:25 p.m.

1 stop5h 15m

Chicago O'Hare Intl

Sat 13/6

5:30 p.m.-1:00 a.m.

1 stop8h 30m

C$ 584

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 16/9

12:40 p.m.-7:48 p.m.

1 stop6h 08m

Chicago O'Hare Intl

Sat 19/9

9:50 a.m.-7:05 p.m.

1 stop10h 15m

C$ 595
Quickest round-trip

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 12/6

10:45 a.m.-7:31 p.m.

1 stop7h 46m

Chicago O'Hare Intl

Sat 20/6

12:46 p.m.-5:20 p.m.

1 stop5h 34m

C$ 597

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 16/9

10:45 a.m.-8:24 p.m.

2 stops8h 39m

Chicago O'Hare Intl

Sat 19/9

1:35 p.m.-11:20 p.m.

2 stops10h 45m

C$ 608

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 22/10

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

2 stops11h 37m

Chicago Midway

Sat 24/10

9:55 a.m.-5:20 p.m.

1 stop8h 25m

C$ 608

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/5

Showing 1-10 of 59 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$ 140). Flying from Saskatchewan to Chicago in September is currently the most expensive (average of C$ 368). 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$ 595, WestJet can have you in Chicago from Saskatchewan in 6h 08m. The distance from Saskatchewan to Chicago is about 1588 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 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.

  • 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$ 140). Flying from Saskatchewan to Chicago in September is currently the most expensive (average of C$ 368). 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
Pierre Elliott Trudeau Intl to Midway flights
Toronto Island to O'Hare Intl flights
Toronto Island to Midway flights
Calgary to O'Hare Intl flights
Vancouver Intl to Midway flights
Ottawa to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Winnipeg to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Québec City to O'Hare Intl flights
Halifax to O'Hare Intl flights
Ottawa to Midway flights
Calgary to Midway flights
Pearson Intl to St. Louis flights
Victoria to O'Hare Intl flights
Halifax to Midway flights
Edmonton to Midway flights
Regina to O'Hare Intl flights
St. John's to O'Hare Intl flights
Québec City to Midway flights
Saskatoon to O'Hare Intl flights
Vancouver Intl to St. Louis flights
Region of Waterloo Intl to O'Hare Intl flights
Victoria to Midway flights
Calgary to St. Louis flights
London to O'Hare Intl flights
Edmonton to St. Louis flights
Nanaimo to O'Hare Intl flights
Pearson Intl to Moline flights
Kelowna to O'Hare Intl flights
Vancouver Intl to Peoria flights
Comox to O'Hare Intl flights
Kelowna to Midway flights
Halifax to St. Louis flights
Ottawa to St. Louis flights
Pearson Intl to Champaign flights
Grande Prairie to O'Hare Intl flights
Deer Lake to O'Hare Intl flights
Saskatoon to Midway flights
St John to O'Hare Intl flights
Charlottetown to St. Louis 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 19 May 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 174AverageC$ 505FlexibilityNo 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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