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Cheap flights from Saskatchewan to Chicago from C$ 223

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 25/1. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
11 Jan — 18 Jan1
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 December 2025.

Wed 17/1211:40 a.m.YQR - ORD
2 stops34h 44mMultiple Airlines
Tue 23/126:05 a.m.ORD - YQR
1 stop13h 15mMultiple Airlines
Deal found 10/12C$ 877
Sun 21/128:10 a.m.YXE - ORD
2 stops13h 04mDelta
Sat 10/111:05 a.m.ORD - YXE
2 stops14h 28mDelta
Deal found 10/12C$ 947
Thu 18/128:10 a.m.YXE - ORD
1 stop6h 49mDelta
Thu 25/126:35 a.m.ORD - YXE
1 stop8h 03mDelta
Deal found 11/12C$ 1,052
Wed 17/1210:53 a.m.YQR - ORD
1 stop6h 05mUnited Airlines
Tue 23/122:31 p.m.ORD - YQR
1 stop8h 20mUnited Airlines
Deal found 10/12C$ 1,081
Thu 18/123:40 p.m.YXE - ORD
1 stop20h 42mMultiple Airlines
Thu 25/127:00 a.m.ORD - YXE
2 stops16h 57mMultiple Airlines
Deal found 11/12C$ 1,085
Sat 20/1211:40 a.m.YQR - MDW
1 stop5h 39mWestJet
Mon 22/129:50 a.m.MDW - YQR
2 stops31h 56mWestJet
Deal found 10/12C$ 1,110
Thu 18/127:15 a.m.YQR - ORD
1 stop13h 08mMultiple Airlines
Sun 21/125:08 p.m.ORD - YQR
2 stops17h 26mMultiple Airlines
Deal found 10/12C$ 1,139
Wed 17/126:10 a.m.YQR - ORD
2 stops15h 29mWestJet
Tue 23/1210:00 a.m.ORD - YQR
2 stops39h 56mWestJet
Deal found 10/12C$ 1,156
Sat 20/1211:40 a.m.YQR - ORD
2 stops36h 32mMultiple Airlines
Mon 22/127:38 p.m.ORD - YQR
1 stop22h 42mMultiple Airlines
Deal found 10/12C$ 1,215
Sat 20/1211:40 a.m.YQR - ORD
1 stop6h 44mWestJet
Mon 22/122:20 p.m.ORD - YQR
1 stop11h 36mWestJet
Deal found 10/12C$ 1,249
Fri 19/1211:40 a.m.YQR - MDW
1 stop6h 38mWestJet
Sun 21/125:59 p.m.MDW - YQR
1 stop24h 21mWestJet
Deal found 10/12C$ 1,276
Fri 19/1211:40 a.m.YQR - ORD
1 stop10h 00mMultiple Airlines
Sun 21/125:08 p.m.ORD - YQR
2 stops17h 26mMultiple Airlines
Deal found 10/12C$ 1,314

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 December 2025.

Round-trip from

C$ 317

One-way from

C$ 223

Popular in

February

Cheapest in

September

Average price

C$ 924
WestJet
  • WestJet
  • 9/2-13/2
  • 2 total stops
  • 13h 48m total
  • Saskatchewan to Chicago
Search Deals
25/1
  • 25/1
  • 2 total stops
  • 38h 36m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 141 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 12 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

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Mon 9/2

6:25 a.m.-1:35 p.m.

1 stop7h 10m

Chicago O'Hare Intl

Fri 13/2

2:20 p.m.-8:58 p.m.

1 stop6h 38m

C$ 317

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 14/4

9:45 a.m.-11:57 p.m.

1 stop13h 12m

Chicago O'Hare Intl

Sat 18/4

12:45 p.m.-9:51 p.m.

1 stop10h 06m

C$ 368

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 17/4

9:45 a.m.-7:43 p.m.

1 stop8h 58m

Chicago O'Hare Intl

Fri 24/4

2:18 p.m.-9:51 p.m.

1 stop8h 33m

C$ 368

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 12/4

9:45 a.m.-10:40 p.m.

1 stop11h 55m

Chicago O'Hare Intl

Fri 24/4

2:18 p.m.-9:51 p.m.

1 stop8h 33m

C$ 368

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 14/4

9:45 a.m.-9:13 p.m.

1 stop10h 28m

Chicago O'Hare Intl

Tue 21/4

12:45 p.m.-9:51 p.m.

1 stop10h 06m

C$ 368

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 13/4

9:45 a.m.-11:57 p.m.

1 stop13h 12m

Chicago O'Hare Intl

Tue 21/4

12:45 p.m.-9:51 p.m.

1 stop10h 06m

C$ 368

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 15/4

9:45 a.m.-10:40 p.m.

1 stop11h 55m

Chicago O'Hare Intl

Sat 18/4

12:45 p.m.-9:51 p.m.

1 stop10h 06m

C$ 368

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 18/4

9:45 a.m.-10:40 p.m.

1 stop11h 55m

Chicago O'Hare Intl

Tue 21/4

12:45 p.m.-9:51 p.m.

1 stop10h 06m

C$ 368

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 12/4

9:45 a.m.-10:40 p.m.

1 stop11h 55m

Chicago O'Hare Intl

Tue 21/4

7:00 a.m.-9:51 p.m.

1 stop15h 51m

C$ 368

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 15/4

9:45 a.m.-11:57 p.m.

1 stop13h 12m

Chicago O'Hare Intl

Tue 21/4

12:45 p.m.-9:51 p.m.

1 stop10h 06m

C$ 368

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 39 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 12 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.

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$ 466, WestJet can have you in Chicago from Saskatchewan in 6h 25m. The distance from Saskatchewan to Chicago is about 1613 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 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

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.
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
Pierre Elliott Trudeau Intl to Midway flights
Vancouver Intl to Midway flights
Calgary to O'Hare Intl flights
Pearson Intl to St. Louis flights
Winnipeg to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Halifax to O'Hare Intl flights
Calgary to Midway flights
Halifax to Midway flights
Edmonton to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Québec City to Midway flights
Saskatoon to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Regina to O'Hare Intl flights
Québec City to O'Hare Intl flights
Ottawa to Midway flights
Vancouver Intl to St. Louis flights
Ottawa to St. Louis flights
Edmonton to Midway flights
Victoria to O'Hare Intl flights
Edmonton to St. Louis flights
Saskatoon to Midway flights
Kelowna to O'Hare Intl flights
Calgary to St. Louis flights
Fort McMurray to O'Hare Intl flights
London to O'Hare Intl flights
Kelowna to Midway flights
Halifax to St. Louis flights
Victoria to St. Louis flights
Nanaimo to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
Pearson Intl to Peoria flights
Vancouver Intl to Peoria flights
St. John's to O'Hare Intl flights
Pearson Intl to Moline flights
Saskatoon to St. Louis flights
Region of Waterloo Intl to O'Hare Intl flights
Deer Lake to O'Hare Intl flights
Québec City to St. Louis flights
Charlottetown to St. Louis 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 12 December 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 175AverageC$ 433FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 406AverageC$ 1,138FlexibilityNo 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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