Find flights
When to book
FAQs

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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
11 Jun — 18 Jun1
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 May 2026.

Thu 28/57:00 a.m.
YXE
-
ORD
1 stop8h 40m
WestJet
Fri 5/65:30 p.m.
ORD
-
YXE
1 stop8h 30m
WestJet
Deal found 7/5C$ 403
Mon 17/87:00 a.m.
YXE
-
ORD
1 stop8h 40m
WestJet
Sat 22/85:30 p.m.
ORD
-
YXE
1 stop8h 30m
WestJet
Deal found 11/5C$ 427
Tue 18/87:00 a.m.
YXE
-
ORD
1 stop8h 40m
WestJet
Mon 24/85:30 p.m.
ORD
-
YXE
1 stop6h 40m
WestJet
Deal found 10/5C$ 454
Tue 29/97:00 a.m.
YQR
-
ORD
1 stop8h 40m
WestJet
Mon 5/105:30 p.m.
ORD
-
YQR
1 stop6h 50m
WestJet
Deal found 9/5C$ 464
Mon 20/73:30 p.m.
YXE
-
ORD
2 stops24h 10m
WestJet
Sat 25/75:30 p.m.
ORD
-
YXE
1 stop6h 40m
WestJet
Deal found 10/5C$ 476
Mon 17/87:00 a.m.
YXE
-
ORD
1 stop8h 40m
WestJet
Wed 19/85:30 p.m.
ORD
-
YXE
1 stop8h 30m
WestJet
Deal found 11/5C$ 505
Wed 17/69:45 a.m.
YQR
-
ORD
1 stop13h 59m
United Airlines
Sat 20/61:30 p.m.
ORD
-
YQR
1 stop9h 00m
United Airlines
Deal found 9/5C$ 518
Fri 25/97:50 p.m.
YXE
-
ORD
1 stop16h 33m
Air Canada
Sat 26/93:45 p.m.
ORD
-
YXE
1 stop8h 31m
Air Canada
Deal found 7/5C$ 529
Fri 29/59:45 a.m.
YQR
-
ORD
1 stop12h 04m
United Airlines
Sat 6/66:00 a.m.
ORD
-
YQR
1 stop16h 30m
United Airlines
Deal found 10/5C$ 533
Fri 29/59:45 a.m.
YQR
-
ORD
1 stop8h 06m
United Airlines
Sat 30/56:00 a.m.
ORD
-
YQR
1 stop16h 30m
United Airlines
Deal found 10/5C$ 548
Wed 23/96:00 a.m.
YXE
-
MDW
2 stops11h 31m
Delta
Sat 26/91:00 p.m.
MDW
-
YXE
2 stops11h 10m
Delta
Deal found 8/5C$ 550
Mon 8/610:45 a.m.
YQR
-
ORD
1 stop6h 24m
Multiple Airlines
Thu 11/68:19 p.m.
ORD
-
YQR
1 stop22h 01m
Multiple Airlines
Deal found 10/5C$ 554

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 May 2026.

Round-trip from

C$ 403

One-way from

C$ 223
WestJet
  • WestJet
  • 28/5-5/6
  • 2 total stops
  • 17h 10m total
  • Saskatchewan to Chicago
Search Deals
WestJet
  • WestJet
  • 11/10
  • 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 12 May 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 - ORD

YXEORD

Saskatoon

Thu 28/5

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

1 stop6h 50m

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-8:15 a.m.

2 stops39h 45m

C$ 485

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Mon 20/7

8:55 p.m.-4:40 p.m.

1 stop18h 45m

Chicago O'Hare Intl

Sat 25/7

5:30 p.m.-1:00 a.m.

1 stop8h 30m

C$ 495

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Mon 17/8

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

1 stop6h 50m

Chicago O'Hare Intl

Wed 19/8

5:30 p.m.-1:00 a.m.

1 stop8h 30m

C$ 505

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 25/9

7:50 p.m.-1:23 p.m.

1 stop16h 33m

Chicago O'Hare Intl

Sat 26/9

3:45 p.m.-11:16 p.m.

1 stop8h 31m

C$ 529

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Wed 23/9

6:00 a.m.-6:31 p.m.

2 stops11h 31m

Chicago Midway

Sat 26/9

1:00 p.m.-11:10 p.m.

2 stops11h 10m

C$ 550

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 5/6

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

1 stop8h 40m

Chicago O'Hare Intl

Sun 7/6

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

2 stops12h 50m

C$ 565

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Mon 10/8

6:00 a.m.-5:39 p.m.

3 stops10h 39m

Chicago O'Hare Intl

Sat 15/8

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

1 stop6h 40m

C$ 596

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 15/6

10:45 a.m.-11:59 p.m.

2 stops12h 14m

Chicago O'Hare Intl

Thu 25/6

12:27 p.m.-5:20 p.m.

1 stop5h 53m

C$ 596
Quickest round-trip

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 7/7

3:10 p.m.-9:52 p.m.

1 stop5h 42m

Chicago O'Hare Intl

Sat 11/7

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

1 stop6h 40m

C$ 600

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 15/6

9:45 a.m.-12:44 a.m.

1 stop13h 59m

Chicago O'Hare Intl

Wed 17/6

1:30 p.m.-9:30 p.m.

1 stop9h 00m

C$ 607

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/5

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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, February is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 139). Flying from Saskatchewan to Chicago in September is currently the most expensive (average of C$ 366). 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$ 485, WestJet can have you in Chicago from Saskatchewan in 6h 50m. 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 Regina - Chicago O'Hare Intl. You may also consider Regina - Chicago Midway or Saskatoon - Chicago O'Hare Intl.

  • 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, February is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 139). Flying from Saskatchewan to Chicago in September is currently the most expensive (average of C$ 366). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Pearson Intl to Midway flights
Toronto Island to Midway flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Calgary to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Ottawa to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Vancouver Intl to Midway flights
Québec City to O'Hare Intl flights
Halifax to O'Hare Intl flights
Calgary to Midway flights
Pearson Intl to St. Louis flights
Edmonton to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Ottawa to Midway flights
Pierre Elliott Trudeau Intl to St. Louis flights
Halifax to Midway flights
Regina to O'Hare Intl flights
Edmonton to Midway flights
Victoria to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights
Vancouver Intl to St. Louis flights
Saskatoon to O'Hare Intl flights
Québec City to Midway flights
Calgary to St. Louis flights
Saskatoon to Midway flights
Pearson Intl to Moline flights
London to O'Hare Intl flights
Victoria to Midway flights
Kelowna to O'Hare Intl flights
Charlottetown to St. Louis flights
Moncton to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Vancouver Intl to Peoria flights
Kelowna to Midway flights
Ottawa to St. Louis flights
Saskatoon to St. Louis flights
Halifax to St. Louis flights
Edmonton to St. Louis flights
Halifax to Peoria flights
Victoria to St. Louis flights
St. John's to O'Hare Intl flights
St John to O'Hare Intl flights
Deer Lake to O'Hare Intl 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 12 May 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 173AverageC$ 480FlexibilityNo 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.