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Cheap flights from Saskatchewan to Chicago from C$ 184

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 15/3. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
5 Feb — 12 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Saskatchewan to Chicago

Keep the following information in mind while searching for Saskatchewan to Chicago flight deals. Data was last updated 6 January 2026.

Round-trip from

C$ 262

One-way from

C$ 184

Popular in

February

Cheapest in

April

Average price

C$ 496
WestJet
  • WestJet
  • 29/1-2/2
  • 3 total stops
  • 27h 43m total
  • Saskatchewan to Chicago
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WestJet
  • WestJet
  • 15/3
  • 2 total stops
  • 19h 25m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 150 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 50 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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Find 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 6 January 2026.

Thu 29/14:30 p.m.YXE - ORD
2 stops21h 05mWestJet
Mon 2/22:20 p.m.ORD - YXE
1 stop6h 38mWestJet
Deal found 6/1C$ 262
Tue 14/45:00 a.m.YXE - ORD
1 stop7h 00mAir Canada
Sat 18/47:55 a.m.ORD - YXE
1 stop6h 36mAir Canada
Deal found 5/1C$ 322
Thu 5/25:00 a.m.YQR - ORD
1 stop8h 01mAir Canada
Sun 8/23:55 p.m.ORD - YQR
1 stop7h 24mAir Canada
Deal found 3/1C$ 401
Thu 5/210:45 a.m.YQR - ORD
1 stop8h 01mUnited Airlines
Sun 8/27:00 a.m.ORD - YQR
1 stop15h 51mUnited Airlines
Deal found 3/1C$ 402
Mon 2/35:00 a.m.YQR - ORD
1 stop14h 45mAir Canada
Tue 3/38:40 p.m.ORD - YQR
1 stop13h 59mAir Canada
Deal found 5/1C$ 428
Thu 18/68:10 p.m.YQR - ORD
1 stop11h 50mAir Canada
Mon 22/69:50 a.m.ORD - YQR
1 stop10h 20mAir Canada
Deal found 4/1C$ 431
Tue 14/48:35 a.m.YXE - ORD
2 stops12h 18mDelta
Sat 18/46:15 a.m.ORD - YXE
2 stops12h 34mDelta
Deal found 5/1C$ 452
Tue 14/48:35 a.m.YXE - MDW
2 stops9h 10mDelta
Sat 18/41:10 p.m.MDW - YXE
2 stops12h 20mDelta
Deal found 5/1C$ 457
Wed 18/35:00 a.m.YXE - ORD
1 stop7h 01mAir Canada
Wed 25/38:40 p.m.ORD - YXE
1 stop13h 40mAir Canada
Deal found 3/1C$ 464
Thu 18/65:30 p.m.YQR - ORD
2 stops22h 13mWestJet
Mon 22/65:30 p.m.ORD - YQR
1 stop8h 37mWestJet
Deal found 4/1C$ 480
Mon 2/311:40 a.m.YQR - MDW
1 stop7h 00mDelta
Tue 3/37:20 p.m.MDW - YQR
1 stop23h 11mDelta
Deal found 5/1C$ 487
Thu 5/211:35 a.m.YQR - ORD
2 stops9h 30mDelta
Sun 8/28:50 a.m.ORD - YQR
1 stop9h 41mDelta
Deal found 3/1C$ 501

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 6 January 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

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 29/1

4:30 p.m.-1:35 p.m.

2 stops21h 05m

Chicago O'Hare Intl

Mon 2/2

2:20 p.m.-8:58 p.m.

1 stop6h 38m

C$ 262

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 14/4

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

1 stop7h 00m

Chicago O'Hare Intl

Sat 18/4

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

1 stop6h 36m

C$ 322

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 5/2

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

1 stop8h 01m

Chicago O'Hare Intl

Sun 8/2

3:55 p.m.-11:19 p.m.

1 stop7h 24m

C$ 401

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 2/3

5:00 a.m.-7:45 p.m.

1 stop14h 45m

Chicago O'Hare Intl

Tue 3/3

8:40 p.m.-10:39 a.m.

1 stop13h 59m

C$ 428

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 18/6

8:10 p.m.-9:00 a.m.

1 stop11h 50m

Chicago O'Hare Intl

Mon 22/6

9:50 a.m.-7:10 p.m.

1 stop10h 20m

C$ 431

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 14/4

8:35 a.m.-9:53 p.m.

2 stops12h 18m

Chicago O'Hare Intl

Sat 18/4

6:15 a.m.-5:49 p.m.

2 stops12h 34m

C$ 452

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Tue 14/4

8:35 a.m.-6:45 p.m.

2 stops9h 10m

Chicago Midway

Sat 18/4

1:10 p.m.-12:30 a.m.

2 stops12h 20m

C$ 457

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 18/6

5:30 p.m.-4:43 p.m.

2 stops22h 13m

Chicago O'Hare Intl

Mon 22/6

5:30 p.m.-1:07 a.m.

1 stop8h 37m

C$ 480

ReginaChicago

YQR - MDW

YQRMDW

Regina

Mon 2/3

11:40 a.m.-6:40 p.m.

1 stop7h 00m

Chicago Midway

Tue 3/3

7:20 p.m.-6:31 p.m.

1 stop23h 11m

C$ 487

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 5/2

11:35 a.m.-9:05 p.m.

2 stops9h 30m

Chicago O'Hare Intl

Sun 8/2

8:50 a.m.-6:31 p.m.

1 stop9h 41m

C$ 501

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 39 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$ 322, WestJet can have you in Chicago from Saskatchewan in 7h. 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 Regina - 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.

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
Toronto Island to Midway flights
Pearson Intl to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Toronto Island to O'Hare Intl flights
Calgary to O'Hare Intl flights
Vancouver Intl to Midway flights
Ottawa to O'Hare Intl flights
Pearson Intl to St. Louis flights
Winnipeg to O'Hare Intl flights
Vancouver Intl to St. Louis flights
Pierre Elliott Trudeau Intl to St. Louis flights
Calgary to Midway flights
Ottawa to Midway flights
Québec City to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Halifax to O'Hare Intl flights
Halifax to Midway flights
Victoria to O'Hare Intl flights
Edmonton to Midway flights
Hamilton to O'Hare Intl flights
Québec City to Midway flights
Calgary to St. Louis flights
Ottawa to St. Louis flights
Halifax to St. Louis flights
Vancouver Intl to Peoria flights
Saskatoon to O'Hare Intl flights
Pearson Intl to Peoria flights
St. John's to O'Hare Intl flights
London to O'Hare Intl flights
Regina to O'Hare Intl flights
Pearson Intl to Bloomington flights
Québec City to St. Louis flights
Edmonton to St. Louis flights
Region of Waterloo Intl to O'Hare Intl flights
Moncton to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Victoria to Midway flights
Sudbury to O'Hare Intl flights
Pearson Intl to Moline flights
Saskatoon to St. Louis flights
Grande Prairie to Midway flights
Charlottetown to St. Louis flights
Saskatoon to Midway flights
Halifax to Peoria 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 6 January 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 174AverageC$ 428FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 409AverageC$ 1,232FlexibilityNo 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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