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Cheap flights from Saskatchewan to Chicago from C$ 151

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 23/10. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
17 Oct — 24 Oct1
1 adult
1 adult, Economy

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 17 September 2025.

Round-trip from

C$ 292

One-way from

C$ 151

Popular in

February

Cheapest in

September

Average price

C$ 422
WestJet
  • WestJet
  • 29/1-2/2
  • 2 total stops
  • 35h 16m total
  • Saskatchewan to Chicago
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WestJet
  • WestJet
  • 23/10
  • 1 total stop
  • 7h 08m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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Find flight deals from Saskatchewan to Chicago

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 September 2025.

Mon 20/109:45 a.m.YQR - ORD
1 stop11h 54mUnited Airlines
Fri 24/102:53 p.m.ORD - YQR
1 stop7h 43mUnited Airlines
Deal found 15/9C$ 296
Thu 2/108:45 p.m.YXE - ORD
1 stop18h 58mWestJet
Mon 6/105:30 p.m.ORD - YXE
1 stop17h 54mWestJet
Deal found 15/9C$ 325
Mon 20/1010:15 a.m.YQR - ORD
1 stop7h 24mMultiple Airlines
Fri 24/105:30 p.m.ORD - YQR
2 stops24h 31mMultiple Airlines
Deal found 15/9C$ 356
Tue 21/105:30 p.m.YQR - ORD
2 stops46h 13mWestJet
Fri 24/105:30 p.m.ORD - YQR
1 stop6h 31mWestJet
Deal found 15/9C$ 363
Sat 8/119:45 p.m.YXE - ORD
2 stops12h 53mMultiple Airlines
Sat 15/118:30 p.m.ORD - YXE
1 stop26h 52mMultiple Airlines
Deal found 17/9C$ 477
Sat 8/1111:30 a.m.YXE - ORD
2 stops24h 07mUnited Airlines
Sat 15/116:28 p.m.ORD - YXE
1 stop16h 07mUnited Airlines
Deal found 15/9C$ 480
Fri 26/93:45 p.m.YXE - ORD
1 stop19h 54mWestJet
Tue 30/95:30 p.m.ORD - YXE
1 stop8h 23mWestJet
Deal found 15/9C$ 481
Thu 2/105:20 a.m.YXE - MDW
2 stops11h 15mDelta
Mon 6/101:48 p.m.MDW - YXE
1 stop8h 36mDelta
Deal found 15/9C$ 633
Sat 8/114:30 p.m.YXE - MDW
2 stops17h 22mWestJet
Sat 15/1111:05 a.m.MDW - YXE
2 stops14h 28mWestJet
Deal found 17/9C$ 889
Mon 20/102:25 p.m.YQR - ORD
2 stops16h 35mAir Canada
Fri 24/108:40 a.m.ORD - YQR
2 stops10h 33mAir Canada
Deal found 15/9C$ 923
Thu 2/105:20 a.m.YXE - MDW
2 stops11h 15mWestJet
Mon 6/109:20 a.m.MDW - YXE
2 stops11h 27mWestJet
Deal found 15/9C$ 992
Sat 8/116:25 a.m.YXE - MDW
2 stops32h 55mMultiple Airlines
Sat 15/119:41 a.m.MDW - YXE
3 stops16h 08mMultiple Airlines
Deal found 15/9C$ 1,347

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 September 2025.
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

9:45 p.m.-1:35 p.m.

1 stop15h 50m

Chicago O'Hare Intl

Mon 2/2

2:20 p.m.-9:46 a.m.

1 stop19h 26m

C$ 292

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 20/10

9:45 a.m.-10:39 p.m.

1 stop11h 54m

Chicago O'Hare Intl

Fri 24/10

2:53 p.m.-9:36 p.m.

1 stop7h 43m

C$ 296

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 21/10

9:45 a.m.-10:39 p.m.

1 stop11h 54m

Chicago O'Hare Intl

Fri 24/10

2:53 p.m.-9:36 p.m.

1 stop7h 43m

C$ 296

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 2/10

8:45 p.m.-4:43 p.m.

1 stop18h 58m

Chicago O'Hare Intl

Mon 6/10

5:30 p.m.-10:24 a.m.

1 stop17h 54m

C$ 325

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 20/10

10:15 a.m.-6:39 p.m.

1 stop7h 24m

Chicago O'Hare Intl

Fri 24/10

5:30 p.m.-5:01 p.m.

2 stops24h 31m

C$ 356

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 21/10

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

2 stops46h 13m

Chicago O'Hare Intl

Fri 24/10

5:30 p.m.-11:01 p.m.

1 stop6h 31m

C$ 363

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sat 8/11

9:45 p.m.-10:38 a.m.

2 stops12h 53m

Chicago O'Hare Intl

Sat 15/11

8:30 p.m.-11:22 p.m.

1 stop26h 52m

C$ 477

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sat 8/11

11:30 a.m.-11:37 a.m.

2 stops24h 07m

Chicago O'Hare Intl

Sat 15/11

6:28 p.m.-10:35 a.m.

1 stop16h 07m

C$ 480

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sun 25/1

8:10 a.m.-6:08 p.m.

1 stop9h 58m

Chicago Midway

Tue 10/3

9:20 a.m.-1:37 p.m.

1 stop5h 17m

C$ 542

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Thu 2/10

5:20 a.m.-5:35 p.m.

2 stops11h 15m

Chicago Midway

Mon 6/10

1:48 p.m.-9:24 p.m.

1 stop8h 36m

C$ 633

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/9

Showing 1-10 of 43 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

What is the cheapest month to book a flight from Saskatchewan to Chicago?

Currently, January is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 261). Flying from Saskatchewan to Chicago in March is currently the most expensive (average of C$ 348). 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.

What is the cheapest time of day to fly from SK to CHI?

Find hourly flight availability from Saskatchewan to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 17 September 2025.

When flying from Saskatchewan to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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$ 542, WestJet can have you in Chicago from Saskatchewan in 9h 58m. 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 cheapest airlines to fly from Saskatchewan to Chicago one-way?

    The cheapest airlines for a one-way flight from Saskatchewan to Chicago are WestJet (C$ 151), Air Canada (C$ 171), and United Airlines (C$ 175).

  • 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 Saskatoon - 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, January is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 261). Flying from Saskatchewan to Chicago in March is currently the most expensive (average of C$ 348). 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

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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.
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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 17 September 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 372AverageC$ 732FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 399AverageC$ 826FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 462AverageC$ 606FlexibilityNo cancel feeOn-timeN/A
Search Delta 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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