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Cheap flights from Saskatchewan to Chicago from C$ 194

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 22/2. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
7 Feb — 14 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 8 January 2026.

Round-trip from

C$ 261

One-way from

C$ 194

Popular in

February

Cheapest in

April

Average price

C$ 498
WestJet
  • WestJet
  • 29/1-2/2
  • 3 total stops
  • 27h 43m total
  • Saskatchewan to Chicago
Search Deals
Air Canada
  • Air Canada
  • 22/2
  • 1 total stop
  • 8h 01m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 151 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 8 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 7/1C$ 261
Tue 19/57:55 a.m.YXE - ORD
1 stop7h 48mWestJet
Sat 23/55:30 p.m.ORD - YXE
1 stop17h 53mWestJet
Deal found 6/1C$ 276
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$ 323
Tue 14/48:35 a.m.YXE - MDW
2 stops9h 10mDelta
Sat 18/42:12 p.m.MDW - YXE
2 stops11h 36mDelta
Deal found 7/1C$ 395
Tue 14/48:35 a.m.YXE - ORD
2 stops8h 29mDelta
Sat 18/412:45 p.m.ORD - YXE
2 stops13h 03mDelta
Deal found 6/1C$ 397
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 6/1C$ 428
Wed 8/49:45 a.m.YQR - ORD
1 stop13h 45mUnited Airlines
Mon 13/42:00 p.m.ORD - YQR
1 stop9h 12mUnited Airlines
Deal found 7/1C$ 448
Thu 9/45:00 a.m.YQR - ORD
1 stop8h 01mUnited Airlines
Mon 13/42:00 p.m.ORD - YQR
1 stop9h 12mUnited Airlines
Deal found 7/1C$ 452
Thu 9/43:25 p.m.YQR - ORD
1 stop21h 10mMultiple Airlines
Mon 13/47:15 a.m.ORD - YQR
2 stops28h 29mMultiple Airlines
Deal found 7/1C$ 475
Mon 2/311:40 a.m.YQR - MDW
1 stop7h 00mDelta
Tue 3/37:20 p.m.MDW - YQR
1 stop23h 11mDelta
Deal found 7/1C$ 488
Wed 8/410:40 a.m.YQR - MDW
1 stop7h 00mDelta
Mon 13/47:18 p.m.MDW - YQR
1 stop24h 03mDelta
Deal found 7/1C$ 491
Wed 8/45:00 a.m.YQR - ORD
1 stop7h 00mAir Canada
Mon 13/412:50 p.m.ORD - YQR
2 stops21h 42mAir Canada
Deal found 7/1C$ 626

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 8 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$ 261

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 6/2

6:25 a.m.-1:35 p.m.

1 stop7h 10m

Chicago O'Hare Intl

Mon 2/3

2:20 p.m.-11:22 a.m.

1 stop21h 02m

C$ 271

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Mon 9/2

6:25 a.m.-1:35 p.m.

1 stop7h 10m

Chicago O'Hare Intl

Sat 28/2

4:29 p.m.-11:18 p.m.

2 stops30h 49m

C$ 372

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Tue 14/4

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

2 stops9h 10m

Chicago Midway

Sat 18/4

2:12 p.m.-12:48 a.m.

2 stops11h 36m

C$ 395

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 14/4

8:35 a.m.-6:04 p.m.

2 stops8h 29m

Chicago O'Hare Intl

Sat 18/4

12:45 p.m.-12:48 a.m.

2 stops13h 03m

C$ 397

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

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 6/2

6:25 a.m.-1:35 p.m.

1 stop7h 10m

Chicago O'Hare Intl

Mon 2/3

7:00 a.m.-3:58 p.m.

3 stops32h 58m

C$ 431

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 8/4

9:45 a.m.-12:30 a.m.

1 stop13h 45m

Chicago O'Hare Intl

Mon 13/4

2:00 p.m.-10:12 p.m.

1 stop9h 12m

C$ 448

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 9/4

5:00 a.m.-2:01 p.m.

1 stop8h 01m

Chicago O'Hare Intl

Mon 13/4

2:00 p.m.-10:12 p.m.

1 stop9h 12m

C$ 452

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 9/4

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

1 stop7h 00m

Chicago O'Hare Intl

Sun 12/4

9:05 a.m.-10:12 p.m.

1 stop14h 07m

C$ 452

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/1

Showing 1-10 of 31 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$ 395, WestJet can have you in Chicago from Saskatchewan in 9h 10m. The distance from Saskatchewan to Chicago is about 1833 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

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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
Toronto Island to Midway flights
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Pearson Intl to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Toronto Island to O'Hare Intl flights
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Ottawa to O'Hare Intl flights
Pearson Intl to St. Louis flights
Vancouver Intl to Midway flights
Winnipeg to O'Hare Intl flights
Ottawa to Midway flights
Vancouver Intl to St. Louis flights
Pierre Elliott Trudeau Intl to St. Louis flights
Calgary to Midway flights
Edmonton to O'Hare Intl flights
Québec City to O'Hare Intl flights
Edmonton to Midway flights
Hamilton to O'Hare Intl flights
Halifax to O'Hare Intl flights
Québec City to Midway flights
Victoria to O'Hare Intl flights
Halifax to Midway flights
Calgary to St. Louis flights
Moncton to O'Hare Intl flights
Victoria to Midway flights
Saskatoon to O'Hare Intl flights
St. John's to O'Hare Intl flights
Vancouver Intl to Peoria flights
Region of Waterloo Intl to O'Hare Intl flights
Ottawa to St. Louis flights
Edmonton to St. Louis flights
London to O'Hare Intl flights
Pearson Intl to Bloomington flights
Saskatoon to Midway flights
Québec City to St. Louis flights
Pearson Intl to Peoria flights
Victoria to St. Louis flights
Kelowna to O'Hare Intl flights
St John to O'Hare Intl flights
Halifax to St. Louis flights
Regina to O'Hare Intl flights
Fort McMurray to O'Hare Intl flights
Deer Lake to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Sudbury 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 8 January 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 175AverageC$ 430FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 411AverageC$ 1,237FlexibilityNo 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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