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Cheap flights from Saskatchewan to Chicago from C$ 234

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
17 Jul — 24 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 17 June 2026.

Thu 3/93:30 p.m.
YXE
-
ORD
2 stops24h 10m
WestJet
Mon 7/95:30 p.m.
ORD
-
YXE
1 stop6h 40m
WestJet
Deal found 15/6C$ 475
Tue 14/710:10 a.m.
YXE
-
ORD
2 stops29h 30m
WestJet
Mon 20/75:30 p.m.
ORD
-
YXE
1 stop8h 30m
WestJet
Deal found 17/6C$ 511
Tue 20/105:45 a.m.
YQR
-
ORD
1 stop8h 10m
Air Canada
Sat 24/108:45 a.m.
ORD
-
YQR
2 stops11h 20m
Air Canada
Deal found 16/6C$ 519
Sun 22/118:10 a.m.
YXE
-
ORD
1 stop6h 47m
Delta
Tue 24/116:00 a.m.
ORD
-
YXE
1 stop8h 38m
Delta
Deal found 16/6C$ 525
Sun 22/116:00 a.m.
YQR
-
ORD
1 stop8h 56m
Air Canada
Mon 23/116:30 p.m.
ORD
-
YQR
1 stop16h 09m
Air Canada
Deal found 12/6C$ 543
Sat 19/99:45 a.m.
YQR
-
ORD
1 stop13h 14m
Multiple Airlines
Sat 26/98:45 a.m.
ORD
-
YQR
2 stops11h 20m
Multiple Airlines
Deal found 12/6C$ 545
Sun 1/116:00 a.m.
YQR
-
ORD
1 stop6h 56m
Air Canada
Tue 19/16:30 p.m.
ORD
-
YQR
1 stop16h 09m
Air Canada
Deal found 13/6C$ 547
Sun 1/1112:45 p.m.
YQR
-
ORD
1 stop6h 49m
Delta
Tue 19/112:15 p.m.
ORD
-
YQR
2 stops12h 40m
Delta
Deal found 13/6C$ 556
Sat 19/99:45 a.m.
YQR
-
ORD
1 stop9h 37m
United Airlines
Sat 26/92:30 p.m.
ORD
-
YQR
1 stop8h 11m
United Airlines
Deal found 12/6C$ 557
Wed 15/79:45 a.m.
YQR
-
ORD
1 stop13h 59m
United Airlines
Tue 21/76:00 a.m.
ORD
-
YQR
1 stop16h 30m
United Airlines
Deal found 16/6C$ 561
Mon 19/107:00 a.m.
YQR
-
MDW
2 stops10h 37m
Delta
Wed 21/1012:30 p.m.
MDW
-
YQR
1 stop5h 50m
Delta
Deal found 15/6C$ 578
Sat 31/106:00 a.m.
YXE
-
MDW
2 stops11h 37m
Delta
Wed 4/119:30 a.m.
MDW
-
YXE
2 stops16h 00m
Delta
Deal found 12/6C$ 615

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 17 June 2026.

Round-trip from

C$ 475

One-way from

C$ 234
WestJet
  • WestJet
  • 3/9-7/9
  • 3 total stops
  • 30h 50m 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 17 June 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

Thu 3/9

2:00 p.m.-4:40 p.m.

1 stop25h 40m

Chicago O'Hare Intl

Mon 7/9

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

1 stop8h 30m

C$ 496

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sun 22/11

8:10 a.m.-2:57 p.m.

1 stop6h 47m

Chicago O'Hare Intl

Tue 24/11

6:00 a.m.-2:38 p.m.

1 stop8h 38m

C$ 540

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 14/7

4:15 p.m.-4:40 p.m.

2 stops23h 25m

Chicago O'Hare Intl

Mon 20/7

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

2 stops23h 00m

C$ 543

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 15/7

9:45 a.m.-12:44 a.m.

1 stop13h 59m

Chicago O'Hare Intl

Tue 21/7

6:00 a.m.-9:30 p.m.

1 stop16h 30m

C$ 561

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 3/7

9:45 a.m.-8:40 p.m.

1 stop9h 55m

Chicago O'Hare Intl

Wed 8/7

8:45 a.m.-7:10 p.m.

2 stops11h 25m

C$ 577

ReginaChicago

YQR - MDW

YQRMDW

Regina

Mon 19/10

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

2 stops10h 37m

Chicago Midway

Wed 21/10

1:00 p.m.-1:10 a.m.

2 stops13h 10m

C$ 578

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 2/9

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

1 stop7h 05m

Chicago O'Hare Intl

Fri 4/9

1:59 p.m.-1:10 a.m.

2 stops12h 11m

C$ 601

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sat 31/10

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

2 stops11h 37m

Chicago Midway

Wed 4/11

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

2 stops16h 00m

C$ 615

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 15/7

10:45 a.m.-5:39 p.m.

1 stop5h 54m

Chicago O'Hare Intl

Tue 21/7

11:55 a.m.-7:45 p.m.

2 stops8h 50m

C$ 616

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 18/8

11:35 a.m.-8:20 p.m.

1 stop7h 45m

Chicago O'Hare Intl

Mon 24/8

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

1 stop8h 30m

C$ 617

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/6

Showing 1-10 of 46 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$ 143). Flying from Saskatchewan to Chicago in July is currently the most expensive (average of C$ 399). 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$ 540, WestJet can have you in Chicago from Saskatchewan in 6h 47m. 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 Regina - Chicago Midway or Saskatoon - 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.

  • 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$ 143). Flying from Saskatchewan to Chicago in July is currently the most expensive (average of C$ 399). 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
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Pearson Intl to Midway flights
Toronto Island to O'Hare Intl flights
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Toronto Island to Midway flights
Calgary to O'Hare Intl flights
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Ottawa to O'Hare Intl flights
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Calgary to Midway flights
Pearson Intl to St. Louis flights
Ottawa to Midway flights
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Edmonton to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
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Edmonton to Midway flights
Halifax to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
Québec City to Midway flights
Calgary to St. Louis flights
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Halifax to St. Louis flights
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Victoria to Midway flights
Kelowna to O'Hare Intl flights
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Fort McMurray to O'Hare Intl flights
Pearson Intl to Moline flights
Pearson Intl to Bloomington flights
Kelowna to Midway flights
Vancouver Intl to Peoria flights
St John to O'Hare Intl flights
Moncton to O'Hare Intl flights
Charlottetown to St. Louis flights
St. John's to O'Hare Intl flights
Edmonton to St. Louis flights
Pearson Intl to Peoria flights
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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 17 June 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 177AverageC$ 514FlexibilityNo 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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