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Cheap flights from Saskatchewan to Chicago from C$ 218

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 16/5. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
11 Apr — 18 Apr1
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 12 March 2026.

Thu 11/67:00 a.m.
YQR
-
ORD
1 stop8h 40m
WestJet
Fri 12/65:30 p.m.
ORD
-
YQR
1 stop8h 40m
WestJet
Deal found 7/3C$ 328
Tue 26/58:35 a.m.
YQR
-
ORD
1 stop7h 05m
WestJet
Fri 29/55:30 p.m.
ORD
-
YQR
1 stop8h 40m
WestJet
Deal found 8/3C$ 373
Tue 26/59:45 a.m.
YQR
-
ORD
1 stop13h 59m
United Airlines
Fri 29/57:05 a.m.
ORD
-
YQR
1 stop15h 25m
United Airlines
Deal found 9/3C$ 392
Mon 1/65:45 a.m.
YQR
-
ORD
1 stop8h 10m
Air Canada
Mon 8/68:20 p.m.
ORD
-
YQR
1 stop13h 42m
Air Canada
Deal found 9/3C$ 408
Thu 23/47:10 a.m.
YXE
-
ORD
1 stop10h 08m
Multiple Airlines
Thu 30/45:30 p.m.
ORD
-
YXE
1 stop8h 30m
Multiple Airlines
Deal found 9/3C$ 438
Thu 23/47:15 a.m.
YQR
-
ORD
1 stop8h 45m
Multiple Airlines
Thu 14/55:30 p.m.
ORD
-
YQR
1 stop6h 50m
Multiple Airlines
Deal found 9/3C$ 441
Sat 2/56:00 a.m.
YXE
-
MDW
2 stops10h 58m
Delta
Tue 5/52:12 p.m.
MDW
-
YXE
1 stop8h 23m
Delta
Deal found 8/3C$ 476
Sat 2/56:00 a.m.
YXE
-
ORD
2 stops13h 40m
Delta
Tue 5/511:00 a.m.
ORD
-
YXE
2 stops11h 35m
Delta
Deal found 8/3C$ 476
Mon 27/410:45 a.m.
YQR
-
MDW
1 stop6h 51m
Delta
Wed 29/49:29 a.m.
MDW
-
YQR
1 stop8h 51m
Delta
Deal found 9/3C$ 480
Fri 1/56:00 a.m.
YXE
-
ORD
2 stops13h 40m
Delta
Tue 5/51:36 p.m.
ORD
-
YXE
2 stops8h 59m
Delta
Deal found 11/3C$ 484
Wed 1/410:40 a.m.
YQR
-
MDW
1 stop7h 00m
Delta
Wed 8/42:05 p.m.
MDW
-
YQR
1 stop5h 16m
Delta
Deal found 12/3C$ 509
Thu 23/46:00 a.m.
YXE
-
MDW
2 stops10h 58m
Delta
Thu 30/41:24 p.m.
MDW
-
YXE
2 stops12h 36m
Delta
Deal found 9/3C$ 513

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 12 March 2026.

Round-trip from

C$ 328

One-way from

C$ 218

Popular in

December

Cheapest in

April

Average price

C$ 750
WestJet
  • WestJet
  • 11/6-12/6
  • 2 total stops
  • 17h 20m total
  • Saskatchewan to Chicago
Search Deals
Air Canada
  • Air Canada
  • 16/5
  • 1 total stop
  • 6h 40m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 26% potential increase in price (C$ 303 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 63 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 12 March 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

Thu 11/6

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

1 stop8h 40m

Chicago O'Hare Intl

Fri 12/6

5:30 p.m.-1:10 a.m.

1 stop8h 40m

C$ 328
Quickest round-trip

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 26/5

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

1 stop7h 05m

Chicago O'Hare Intl

Fri 29/5

5:30 p.m.-1:10 a.m.

1 stop8h 40m

C$ 373

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 26/5

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

1 stop13h 59m

Chicago O'Hare Intl

Fri 29/5

7:05 a.m.-9:30 p.m.

1 stop15h 25m

C$ 392

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 23/4

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

1 stop13h 45m

Chicago O'Hare Intl

Sat 25/4

7:00 a.m.-9:30 p.m.

1 stop15h 30m

C$ 445

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 27/4

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

1 stop8h 40m

Chicago O'Hare Intl

Wed 29/4

7:00 a.m.-5:20 p.m.

2 stops11h 20m

C$ 472

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sat 2/5

6:00 a.m.-5:58 p.m.

2 stops10h 58m

Chicago Midway

Tue 5/5

9:27 a.m.-9:35 p.m.

2 stops13h 08m

C$ 476

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sat 2/5

6:00 a.m.-8:40 p.m.

2 stops13h 40m

Chicago O'Hare Intl

Tue 5/5

1:36 p.m.-9:35 p.m.

2 stops8h 59m

C$ 476

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 1/5

6:00 a.m.-8:40 p.m.

2 stops13h 40m

Chicago O'Hare Intl

Tue 5/5

1:36 p.m.-9:35 p.m.

2 stops8h 59m

C$ 484

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 1/6

6:00 a.m.-8:14 p.m.

2 stops13h 14m

Chicago O'Hare Intl

Mon 8/6

10:35 a.m.-11:20 p.m.

2 stops13h 45m

C$ 491

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 23/4

6:00 a.m.-5:58 p.m.

2 stops10h 58m

Chicago Midway

Sat 25/4

9:46 a.m.-6:21 p.m.

1 stop9h 35m

C$ 520

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/3

Showing 1-10 of 48 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

How much does it cost to fly round-trip from Saskatchewan to Chicago?

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$ 328, WestJet can have you in Chicago from Saskatchewan in 8h 40m. 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 Saskatoon - Chicago O'Hare Intl. You may also consider Saskatoon - Chicago Midway 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
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
Ottawa to O'Hare Intl flights
Vancouver Intl to Midway 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
Ottawa to Midway flights
Québec City to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Vancouver Intl to St. Louis flights
Edmonton to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
Halifax to Midway flights
Calgary to St. Louis flights
Kelowna to O'Hare Intl flights
Victoria to O'Hare Intl flights
Ottawa to St. Louis flights
Victoria to St. Louis flights
Québec City to Midway flights
St. John's to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Halifax to St. Louis flights
Edmonton to St. Louis flights
Kelowna to Midway flights
Saskatoon to Midway flights
Fort McMurray to O'Hare Intl flights
Regina to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Québec City to St. Louis flights
Pearson Intl to Champaign flights
Comox to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
Calgary to Decatur flights
Victoria to Midway flights
Pearson Intl to Peoria flights
Vancouver Intl to Peoria flights
Halifax to Peoria flights

Top 3 airlines flying from Saskatchewan to Chicago

Discover the top 3 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 12 March 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 172AverageC$ 418FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 306AverageC$ 504FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 405AverageC$ 953FlexibilityNo cancel feeOn-time67%
Search Air Canada 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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