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Cheap flights from Saskatchewan to Chicago from C$ 199

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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
13 Sep — 20 Sep1
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 14 August 2026.

Fri 28/87:00 a.m. -
1 stop8h 40m
Sun 6/95:30 p.m. -
1 stop8h 30m
Deal found 13/8C$ 347
Thu 10/98:50 a.m. -
1 stop6h 50m
Mon 14/95:30 p.m. -
1 stop6h 40m
Deal found 13/8C$ 434
Fri 4/97:00 a.m. -
1 stop8h 40m
Thu 10/95:30 p.m. -
1 stop6h 40m
Deal found 10/8C$ 464
Fri 25/97:00 a.m. -
1 stop8h 40m
Fri 2/105:30 p.m. -
1 stop6h 50m
Deal found 11/8C$ 475
Thu 22/107:00 a.m. -
1 stop8h 40m
Mon 26/1011:41 a.m. -
1 stop26h 57m
Deal found 13/8C$ 507
Thu 10/98:35 a.m. -
1 stop7h 05m
Sun 13/95:30 p.m. -
1 stop8h 40m
Deal found 12/8C$ 512
Tue 27/1011:45 a.m. -
2 stops21h 16m
Thu 29/107:18 p.m. -
1 stop24h 03m
Deal found 13/8C$ 524
Fri 4/94:30 p.m. -
2 stops17h 30m
Thu 10/93:20 p.m. -
1 stop10h 15m
Deal found 10/8C$ 535
Sat 5/94:15 p.m. -
1 stop23h 25m
Thu 10/95:30 p.m. -
1 stop6h 50m
Deal found 11/8C$ 537
Thu 3/1212:55 p.m. -
1 stop7h 03m
Mon 7/128:50 p.m. -
1 stop13h 51m
Deal found 9/8C$ 544
Sat 10/107:00 a.m. -
2 stops12h 30m
Tue 13/101:55 p.m. -
2 stops12h 05m
Deal found 13/8C$ 551
Thu 10/97:00 a.m. -
1 stop8h 40m
Sun 13/95:30 p.m. -
1 stop8h 40m
Deal found 13/8C$ 567

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 14 August 2026.

Round-trip from

C$ 347

One-way from

C$ 199
WestJet
  • WestJet
  • 28/8-6/9
  • 2 total stops
  • 17h 10m total
  • Saskatchewan to Chicago
Search Deals
WestJet
  • WestJet
  • 6/9
  • 1 total stop
  • 8h 40m total
  • Saskatchewan to Chicago
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 14 August 2026.
Use the filters below to find and compare flights from Saskatchewan to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 28/8

3:30 p.m.-4:40 p.m.

2 stops24h 10m

Chicago O'Hare Intl

Sun 6/9

5:30 p.m.-11:10 p.m.

1 stop6h 40m

C$ 424
Quickest round-trip

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 10/9

8:50 a.m.-4:40 p.m.

1 stop6h 50m

Chicago O'Hare Intl

Mon 14/9

5:30 p.m.-11:10 p.m.

1 stop6h 40m

C$ 434

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 4/9

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Thu 10/9

5:30 p.m.-11:10 p.m.

1 stop6h 40m

C$ 464

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 25/9

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Fri 2/10

5:30 p.m.-11:20 p.m.

1 stop6h 50m

C$ 475

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 3/12

12:55 p.m.-7:58 p.m.

1 stop7h 03m

Chicago O'Hare Intl

Mon 7/12

8:50 p.m.-10:41 a.m.

1 stop13h 51m

C$ 544

SaskatoonChicago

YXE Saskatoon - MDW Chicago Midway

YXEMDW

Saskatoon

Fri 4/9

4:25 p.m.-11:00 a.m.

1 stop17h 35m

Chicago Midway

Thu 10/9

3:20 p.m.-12:35 a.m.

1 stop10h 15m

C$ 551

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sat 10/10

7:00 a.m.-8:30 p.m.

2 stops12h 30m

Chicago O'Hare Intl

Tue 13/10

1:55 p.m.-1:00 a.m.

2 stops12h 05m

C$ 551

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 10/9

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Sun 13/9

5:30 p.m.-1:10 a.m.

1 stop8h 40m

C$ 567

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 9/10

10:45 a.m.-3:03 p.m.

1 stop27h 18m

Chicago O'Hare Intl

Mon 12/10

11:41 a.m.-5:20 p.m.

1 stop6h 39m

C$ 570

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 10/9

8:35 a.m.-4:40 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Sun 13/9

5:30 p.m.-11:15 a.m.

2 stops18h 45m

C$ 570

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/8

Showing 1-10 of 59 resultsSorted by cheapest first
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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, October is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 344). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,051). 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.

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$ 544, WestJet can have you in Chicago from Saskatchewan in 7h 03m. The distance from Saskatchewan to Chicago is about 1809 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.

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

    Currently, October is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 344). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,051). 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.
Pearson Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Toronto Island 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
Calgary to O'Hare Intl flights
Pearson Intl to St. Louis flights
Hamilton to O'Hare Intl flights
Vancouver Intl to Midway flights
Winnipeg to O'Hare Intl flights
Québec City to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Calgary to Midway flights
Pierre Elliott Trudeau Intl to St. Louis flights
Region of Waterloo Intl to O'Hare Intl flights
Halifax to O'Hare Intl flights
Ottawa to Midway flights
Edmonton to Midway flights
Vancouver Intl to St. Louis flights
Edmonton to St. Louis flights
Québec City to Midway flights
Saskatoon to O'Hare Intl flights
Calgary to St. Louis flights
St John to O'Hare Intl flights
Victoria to Midway flights
Halifax to Midway flights
London to O'Hare Intl flights
Regina to O'Hare Intl flights
Victoria to O'Hare Intl flights
Vancouver Intl to Peoria flights
Kelowna to O'Hare Intl flights
Ottawa to St. Louis flights
Saskatoon to Midway flights
Pearson Intl to Bloomington flights
Moncton to O'Hare Intl flights
Fort McMurray to O'Hare Intl flights
Charlottetown to St. Louis flights
Deer Lake to O'Hare Intl flights
St. John's to O'Hare Intl flights
Pearson Intl to Moline flights
Saskatoon to St. Louis flights

Top airline flying from Saskatchewan to Chicago

Discover the top airline 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 14 August 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 176AverageC$ 503FlexibilityNo cancel feeOn-time60%
Search WestJet 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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