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Cheap flights from Saskatchewan to Chicago from C$ 153

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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
23 Aug — 30 Aug1
1 adult

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 18 August 2025.

Round-trip from

C$ 296

One-way from

C$ 153

Popular in

February

Cheapest in

September

Average price

C$ 647
WestJet
  • WestJet
  • 29/1-2/2
  • 2 total stops
  • 22h 28m total
  • Saskatchewan to Chicago
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WestJet
  • WestJet
  • 3/11
  • 1 total stop
  • 7h 10m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 94 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 37 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 18 August 2025.

Fri 26/95:30 p.m.YQR - ORD
1 stop18h 09mWestJet
Tue 30/95:30 p.m.ORD - YQR
1 stop6h 31mWestJet
Deal found 15/8C$ 316
Thu 2/101:00 p.m.YXE - ORD
1 stop26h 43mWestJet
Mon 6/105:30 p.m.ORD - YXE
1 stop8h 23mWestJet
Deal found 17/8C$ 321
Thu 25/98:35 p.m.YQR - ORD
1 stop19h 08mWestJet
Tue 30/95:30 p.m.ORD - YQR
1 stop6h 31mWestJet
Deal found 15/8C$ 347
Thu 2/108:45 p.m.YXE - ORD
1 stop18h 58mWestJet
Thu 9/105:30 p.m.ORD - YXE
2 stops22h 41mWestJet
Deal found 18/8C$ 384
Fri 21/1110:45 a.m.YQR - ORD
1 stop6h 13mUnited Airlines
Mon 24/112:40 p.m.ORD - YQR
1 stop8h 11mUnited Airlines
Deal found 16/8C$ 408
Fri 21/1111:45 a.m.YQR - ORD
2 stops8h 51mDelta
Mon 24/118:55 a.m.ORD - YQR
2 stops9h 22mDelta
Deal found 16/8C$ 434
Mon 8/93:15 p.m.YXE - ORD
2 stops29h 13mMultiple Airlines
Sat 13/91:40 p.m.ORD - YXE
1 stop19h 37mMultiple Airlines
Deal found 18/8C$ 448
Thu 25/91:00 p.m.YXE - ORD
2 stops32h 45mMultiple Airlines
Sun 28/95:30 p.m.ORD - YXE
1 stop14h 50mMultiple Airlines
Deal found 17/8C$ 468
Fri 29/85:50 p.m.YXE - ORD
2 stops21h 36mMultiple Airlines
Mon 1/910:49 a.m.ORD - YXE
1 stop11h 35mMultiple Airlines
Deal found 16/8C$ 499
Sat 23/810:15 a.m.YQR - ORD
1 stop10h 20mDelta
Wed 27/86:10 a.m.ORD - YQR
1 stop11h 20mDelta
Deal found 15/8C$ 887
Thu 25/910:15 a.m.YQR - MDW
1 stop6h 20mWestJet
Tue 30/99:20 a.m.MDW - YQR
1 stop8h 21mWestJet
Deal found 15/8C$ 1,069
Sun 24/810:15 a.m.YQR - ORD
1 stop5h 49mDelta
Wed 27/88:25 a.m.ORD - YQR
1 stop9h 05mDelta
Deal found 15/8C$ 1,086

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 18 August 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.-8:58 p.m.

1 stop6h 38m

C$ 296

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 26/9

5:30 p.m.-12:39 p.m.

1 stop18h 09m

Chicago O'Hare Intl

Tue 30/9

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

1 stop6h 31m

C$ 316

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 2/10

1:00 p.m.-4:43 p.m.

1 stop26h 43m

Chicago O'Hare Intl

Mon 6/10

5:30 p.m.-12:53 a.m.

1 stop8h 23m

C$ 321

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 25/9

8:35 p.m.-4:43 p.m.

1 stop19h 08m

Chicago O'Hare Intl

Tue 30/9

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

1 stop6h 31m

C$ 347

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 21/11

10:45 a.m.-4:58 p.m.

1 stop6h 13m

Chicago O'Hare Intl

Mon 24/11

2:40 p.m.-10:51 p.m.

1 stop8h 11m

C$ 408

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 21/11

11:45 a.m.-8:36 p.m.

2 stops8h 51m

Chicago O'Hare Intl

Mon 24/11

8:55 a.m.-6:17 p.m.

2 stops9h 22m

C$ 434

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 25/9

10:15 a.m.-5:35 p.m.

1 stop6h 20m

Chicago Midway

Tue 30/9

1:43 p.m.-1:17 a.m.

2 stops12h 34m

C$ 1,069

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sat 8/11

11:55 a.m.-1:09 p.m.

2 stops25h 14m

Chicago Midway

Sun 16/11

9:20 a.m.-2:38 p.m.

1 stop5h 18m

C$ 1,255

ReginaChicago

YQR - MDW

YQRMDW

Regina

Fri 26/9

10:15 a.m.-5:35 p.m.

1 stop6h 20m

Chicago Midway

Tue 30/9

9:20 a.m.-4:41 p.m.

1 stop8h 21m

C$ 1,295

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Thu 2/10

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

2 stops11h 15m

Chicago Midway

Mon 6/10

9:20 a.m.-7:40 p.m.

2 stops11h 20m

C$ 1,351

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/8

Showing 1-10 of 41 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$ 352). 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 18 August 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$ 408, WestJet can have you in Chicago from Saskatchewan in 6h 13m. 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 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$ 153), Air Canada (C$ 214), and United Airlines (C$ 225).

  • 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 Saskatoon - 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.

  • 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$ 352). 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 18 August 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 374AverageC$ 735FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 403AverageC$ 725FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 464AverageC$ 609FlexibilityNo 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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