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Cheap flights from Saskatchewan to Chicago from C$ 244

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 29/7. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
8 Jul — 15 Jul1
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 3 July 2025.

Round-trip from

C$ 350

One-way from

C$ 244

Popular in

February

Cheapest in

September

Average price

C$ 601
WestJet
  • WestJet
  • 8/9-13/9
  • 2 total stops
  • 17h 06m total
  • Saskatchewan to Chicago
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WestJet
  • WestJet
  • 29/7
  • 1 total stop
  • 7h 09m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 123 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 3 July 2025.

Mon 8/97:00 a.m.YXE - ORD
1 stop8h 43mWestJet
Sat 13/95:30 p.m.ORD - YXE
1 stop8h 23mWestJet
Deal found 2/7C$ 350
Tue 21/1010:05 a.m.YQR - ORD
1 stop25h 34mWestJet
Fri 24/105:30 p.m.ORD - YQR
1 stop8h 36mWestJet
Deal found 3/7C$ 406
Fri 1/85:20 a.m.YXE - ORD
2 stops15h 10mMultiple Airlines
Thu 7/85:30 p.m.ORD - YXE
1 stop8h 24mMultiple Airlines
Deal found 1/7C$ 459
Fri 15/811:25 a.m.YQR - ORD
1 stop7h 04mAir Canada
Mon 18/88:25 p.m.ORD - YQR
1 stop15h 05mAir Canada
Deal found 2/7C$ 500
Fri 12/96:00 a.m.YXE - ORD
2 stops11h 04mDelta
Sun 14/911:08 a.m.ORD - YXE
2 stops12h 35mDelta
Deal found 2/7C$ 506
Sat 27/95:40 a.m.YXE - MDW
2 stops11h 55mDelta
Tue 30/99:20 a.m.MDW - YXE
2 stops11h 20mDelta
Deal found 2/7C$ 508
Wed 6/86:00 a.m.YXE - ORD
1 stop8h 04mAir Canada
Sun 10/86:20 p.m.ORD - YXE
1 stop6h 39mAir Canada
Deal found 2/7C$ 542
Fri 15/811:45 a.m.YQR - ORD
3 stops16h 05mMultiple Airlines
Mon 18/85:30 p.m.ORD - YQR
1 stop15h 35mMultiple Airlines
Deal found 2/7C$ 566
Fri 25/75:40 a.m.YXE - MDW
1 stop9h 44mMultiple Airlines
Sat 2/89:40 a.m.MDW - YXE
2 stops23h 37mMultiple Airlines
Deal found 2/7C$ 651
Thu 31/75:15 a.m.YXE - ORD
2 stops18h 15mUnited Airlines
Thu 7/83:50 p.m.ORD - YXE
1 stop9h 06mUnited Airlines
Deal found 1/7C$ 713
Fri 15/810:15 a.m.YQR - MDW
1 stop6h 22mDelta
Mon 18/89:15 a.m.MDW - YQR
1 stop8h 15mDelta
Deal found 2/7C$ 721
Tue 21/106:00 a.m.YQR - MDW
2 stops14h 44mWestJet
Fri 24/101:05 p.m.MDW - YQR
2 stops13h 01mWestJet
Deal found 3/7C$ 774

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 3 July 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

Mon 8/9

7:00 a.m.-4:43 p.m.

1 stop8h 43m

Chicago O'Hare Intl

Sat 13/9

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

1 stop8h 23m

C$ 350

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 21/10

10:05 a.m.-12:39 p.m.

1 stop25h 34m

Chicago O'Hare Intl

Fri 24/10

5:30 p.m.-1:06 a.m.

1 stop8h 36m

C$ 406

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 1/8

5:20 a.m.-9:30 p.m.

2 stops15h 10m

Chicago O'Hare Intl

Thu 7/8

5:30 p.m.-12:54 a.m.

1 stop8h 24m

C$ 459

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 15/8

11:25 a.m.-7:29 p.m.

1 stop7h 04m

Chicago O'Hare Intl

Mon 18/8

8:25 p.m.-10:30 a.m.

1 stop15h 05m

C$ 500

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 12/9

6:00 a.m.-6:04 p.m.

2 stops11h 04m

Chicago O'Hare Intl

Sun 14/9

11:08 a.m.-10:43 p.m.

2 stops12h 35m

C$ 506

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sat 27/9

5:40 a.m.-6:35 p.m.

2 stops11h 55m

Chicago Midway

Tue 30/9

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

2 stops11h 20m

C$ 508

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Wed 6/8

6:00 a.m.-3:04 p.m.

1 stop8h 04m

Chicago O'Hare Intl

Sun 10/8

6:20 p.m.-11:59 p.m.

1 stop6h 39m

C$ 542

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 15/8

11:45 a.m.-4:50 a.m.

3 stops16h 05m

Chicago O'Hare Intl

Mon 18/8

5:30 p.m.-8:05 a.m.

1 stop15h 35m

C$ 566

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Fri 25/7

5:40 a.m.-4:24 p.m.

1 stop9h 44m

Chicago Midway

Sat 2/8

9:40 a.m.-8:17 a.m.

2 stops23h 37m

C$ 651

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 31/7

5:15 a.m.-12:30 a.m.

2 stops18h 15m

Chicago O'Hare Intl

Thu 7/8

3:50 p.m.-11:56 p.m.

1 stop9h 06m

C$ 713

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/7

Showing 1-10 of 28 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 3 July 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.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 3 July 2025.
Read through reviews of airlines operating flights from Saskatchewan to Chicago, such as Delta,United Airlines, andWestJet. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,982 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,982 reviews
Delta
8.0
Very good
7,982 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,861 reviews
Delta
8.0
Very good
7,982 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,917 reviews
Delta
8.0
Very good
7,982 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Canada
7.1
Good
9,681 reviews
Delta
8.0
Very good
7,982 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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$ 244), Air Canada (C$ 260), and United Airlines (C$ 268).

  • What are the most popular routes from Saskatchewan to Chicago?

    The most popular route from Saskatchewan to Chicago is Regina - Chicago Midway. 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$ 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

Browse thousands of different options on Cheapflights for your next trip

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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 3 July 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 309AverageC$ 651FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 371AverageC$ 646FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 458AverageC$ 580FlexibilityNo cancel feeOn-timeN/A
Search Delta flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Saskatchewan to Chicago?

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Why should you use Cheapflights to find cheap flight tickets from Saskatchewan to Chicago?

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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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