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Cheap flights from Saskatchewan to Chicago from C$ 175

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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
25 Jan — 1 Feb1
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 26 December 2025.

Mon 29/126:00 a.m.YXE - ORD
1 stop7h 01mUnited Airlines
Tue 6/13:55 p.m.ORD - YXE
1 stop7h 40mUnited Airlines
Deal found 25/12C$ 950
Sun 28/128:35 p.m.YXE - ORD
2 stops24h 57mMultiple Airlines
Mon 5/17:38 p.m.ORD - YXE
1 stop19h 00mMultiple Airlines
Deal found 25/12C$ 999
Mon 29/128:35 p.m.YXE - ORD
2 stops42h 18mMultiple Airlines
Mon 5/17:38 p.m.ORD - YXE
1 stop19h 00mMultiple Airlines
Deal found 25/12C$ 1,013
Mon 29/126:25 a.m.YXE - ORD
1 stop7h 10mWestJet
Mon 5/12:20 p.m.ORD - YXE
1 stop11h 29mWestJet
Deal found 25/12C$ 1,018
Tue 30/126:25 a.m.YXE - ORD
2 stops32h 28mMultiple Airlines
Mon 5/17:38 p.m.ORD - YXE
1 stop19h 00mMultiple Airlines
Deal found 25/12C$ 1,032
Sun 28/128:10 a.m.YXE - ORD
1 stop13h 24mWestJet
Mon 5/12:20 p.m.ORD - YXE
1 stop11h 29mWestJet
Deal found 25/12C$ 1,049
Tue 30/1211:30 a.m.YXE - ORD
2 stops20h 35mAir Canada
Tue 6/13:55 p.m.ORD - YXE
1 stop7h 40mAir Canada
Deal found 25/12C$ 1,084
Tue 30/126:25 a.m.YXE - ORD
2 stops15h 09mWestJet
Mon 5/12:20 p.m.ORD - YXE
2 stops49h 40mWestJet
Deal found 25/12C$ 1,085
Tue 30/129:45 p.m.YXE - MDW
2 stops23h 00mMultiple Airlines
Tue 6/12:03 p.m.MDW - YXE
1 stop9h 54mMultiple Airlines
Deal found 25/12C$ 1,202
Sun 28/128:10 a.m.YXE - MDW
1 stop26h 56mWestJet
Mon 5/11:49 p.m.MDW - YXE
1 stop24h 49mWestJet
Deal found 25/12C$ 1,240
Sun 28/128:10 a.m.YXE - ORD
1 stop13h 24mMultiple Airlines
Sun 4/110:49 p.m.ORD - YXE
2 stops17h 10mMultiple Airlines
Deal found 25/12C$ 1,243
Sun 28/128:10 a.m.YXE - MDW
1 stop9h 09mDelta
Mon 5/11:49 p.m.MDW - YXE
2 stops12h 00mDelta
Deal found 25/12C$ 1,296

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 26 December 2025.

Round-trip from

C$ 294

One-way from

C$ 175

Popular in

February

Cheapest in

September

Average price

C$ 916
WestJet
  • WestJet
  • 30/5-3/6
  • 2 total stops
  • 15h 20m total
  • Saskatchewan to Chicago
Search Deals
9/2
  • 9/2
  • 2 total stops
  • 25h 33m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 153 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 48 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 26 December 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

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 30/5

6:55 a.m.-4:43 p.m.

1 stop8h 48m

Chicago O'Hare Intl

Wed 3/6

5:30 p.m.-11:02 p.m.

1 stop6h 32m

C$ 294

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 7/5

3:45 p.m.-4:43 p.m.

2 stops23h 58m

Chicago O'Hare Intl

Mon 11/5

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

1 stop8h 23m

C$ 321

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$ 323

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 8/1

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

1 stop15h 50m

Chicago O'Hare Intl

Mon 12/1

2:20 p.m.-8:59 p.m.

1 stop6h 39m

C$ 336

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 14/4

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

1 stop7h 00m

Chicago O'Hare Intl

Sat 18/4

7:55 a.m.-1:31 p.m.

1 stop6h 36m

C$ 372

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 8/1

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

1 stop15h 50m

Chicago O'Hare Intl

Tue 13/1

12:00 p.m.-11:57 p.m.

1 stop11h 57m

C$ 390

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 8/1

8:10 a.m.-12:42 a.m.

2 stops16h 32m

Chicago O'Hare Intl

Mon 12/1

2:20 p.m.-8:59 p.m.

1 stop6h 39m

C$ 416

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 9/2

6:10 a.m.-1:35 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Mon 16/2

2:20 p.m.-9:06 p.m.

1 stop6h 46m

C$ 429

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 9/2

11:35 a.m.-9:05 p.m.

2 stops9h 30m

Chicago O'Hare Intl

Mon 16/2

12:29 p.m.-6:31 p.m.

1 stop6h 02m

C$ 465

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Tue 14/4

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

2 stops9h 10m

Chicago Midway

Sat 18/4

9:27 a.m.-12:30 a.m.

2 stops16h 03m

C$ 509

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/12

Showing 1-10 of 32 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 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 26 December 2025.

It’s optimal to fly from Saskatchewan to Chicago in the afternoon. By choosing this option you can save up to 72% on the cost of your flight, compared to a flight at noon.

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$ 294, WestJet can have you in Chicago from Saskatchewan in 8h 48m. 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 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.

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
Toronto Island to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Ottawa to O'Hare Intl flights
Pearson Intl to St. Louis flights
Vancouver Intl to Midway flights
Vancouver Intl to St. Louis flights
Calgary to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Ottawa to Midway flights
Edmonton to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Calgary to Midway flights
Halifax to O'Hare Intl flights
Halifax to Midway flights
Québec City to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Edmonton to Midway flights
Hamilton to O'Hare Intl flights
Pearson Intl to Moline flights
Victoria to O'Hare Intl flights
St. John's to O'Hare Intl flights
Québec City to Midway flights
Ottawa to St. Louis flights
Saskatoon to Midway flights
Regina to O'Hare Intl flights
Halifax to St. Louis flights
Region of Waterloo Intl to O'Hare Intl flights
Victoria to St. Louis flights
Québec City to St. Louis flights
Moncton to O'Hare Intl flights
Edmonton to St. Louis flights
Fort McMurray to O'Hare Intl flights
London to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Pearson Intl to Peoria flights
Saskatoon to St. Louis flights
Calgary to St. Louis flights
Sudbury to O'Hare Intl flights
Kelowna to Midway flights
Grande Prairie to O'Hare Intl flights
Comox to O'Hare Intl flights
Pearson Intl to Bloomington flights
Calgary to Decatur 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 26 December 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 173AverageC$ 425FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 407AverageC$ 1,208FlexibilityNo 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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