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Cheap flights from Saskatchewan to Chicago from C$ 154

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 14/12. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

Find 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 30 October 2025.

Mon 24/116:25 a.m.YXE - ORD
1 stop7h 10mMultiple Airlines
Sun 30/116:13 a.m.ORD - YXE
1 stop8h 25mMultiple Airlines
Deal found 29/10C$ 406
Sat 13/1211:40 a.m.YQR - ORD
1 stop23h 11mMultiple Airlines
Sat 20/125:50 p.m.ORD - YQR
1 stop24h 30mMultiple Airlines
Deal found 30/10C$ 437
Sun 23/118:10 a.m.YXE - ORD
1 stop26h 29mMultiple Airlines
Sat 29/118:22 p.m.ORD - YXE
1 stop18h 16mMultiple Airlines
Deal found 28/10C$ 458
Wed 10/125:00 a.m.YQR - ORD
1 stop8h 01mUnited Airlines
Sat 13/128:45 a.m.ORD - YQR
1 stop14h 12mUnited Airlines
Deal found 29/10C$ 466
Thu 27/118:10 a.m.YXE - ORD
1 stop25h 53mMultiple Airlines
Thu 4/129:53 p.m.ORD - YXE
2 stops21h 57mMultiple Airlines
Deal found 30/10C$ 487
Wed 10/1211:40 a.m.YQR - MDW
1 stop6h 38mDelta
Sat 13/126:00 a.m.MDW - YQR
2 stops12h 20mDelta
Deal found 29/10C$ 490
Thu 18/128:10 a.m.YXE - ORD
1 stop10h 58mMultiple Airlines
Tue 23/126:05 p.m.ORD - YXE
2 stops44h 33mMultiple Airlines
Deal found 29/10C$ 505
Sun 23/118:10 a.m.YXE - ORD
1 stop26h 29mMultiple Airlines
Sun 30/119:18 a.m.ORD - YXE
1 stop5h 20mMultiple Airlines
Deal found 29/10C$ 521
Fri 28/116:25 a.m.YXE - ORD
1 stop7h 10mMultiple Airlines
Mon 1/128:22 p.m.ORD - YXE
1 stop18h 16mMultiple Airlines
Deal found 29/10C$ 561
Thu 27/118:10 a.m.YXE - MDW
2 stops14h 33mMultiple Airlines
Thu 4/1211:00 a.m.MDW - YXE
1 stop14h 33mMultiple Airlines
Deal found 30/10C$ 564
Sun 23/118:10 a.m.YXE - MDW
2 stops16h 03mMultiple Airlines
Sat 29/1112:45 p.m.MDW - YXE
1 stop12h 48mMultiple Airlines
Deal found 28/10C$ 580
Sat 22/117:00 a.m.YXE - MDW
1 stop27h 05mMultiple Airlines
Sat 29/1112:45 p.m.MDW - YXE
1 stop12h 48mMultiple Airlines
Deal found 28/10C$ 588

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 30 October 2025.

Round-trip from

C$ 399

One-way from

C$ 154

Popular in

February

Cheapest in

January

Average price

C$ 533
8/1-18/1
  • 8/1-18/1
  • 3 total stops
  • 66h 39m total
  • Saskatchewan to Chicago
Search Deals
14/12
  • 14/12
  • 1 total stop
  • 26h 06m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 30 October 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

Thu 8/1

4:15 p.m.-9:01 p.m.

1 stop28h 46m

Chicago O'Hare Intl

Sun 18/1

9:52 p.m.-11:45 a.m.

2 stops37h 53m

C$ 399

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 29/1

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

1 stop15h 50m

Chicago O'Hare Intl

Mon 2/2

2:20 p.m.-3:58 p.m.

1 stop25h 38m

C$ 415

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Mon 24/11

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

1 stop7h 10m

Chicago O'Hare Intl

Sun 30/11

6:13 a.m.-2:38 p.m.

1 stop8h 25m

C$ 434

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 13/12

11:40 a.m.-10:51 a.m.

1 stop23h 11m

Chicago O'Hare Intl

Sat 20/12

5:50 p.m.-6:20 p.m.

1 stop24h 30m

C$ 437

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 10/12

5:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago O'Hare Intl

Sat 13/12

8:45 a.m.-10:57 p.m.

1 stop14h 12m

C$ 466

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 28/4

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

1 stop7h 00m

Chicago O'Hare Intl

Sat 2/5

3:45 p.m.-11:56 p.m.

1 stop9h 11m

C$ 475

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 27/11

8:10 a.m.-10:03 a.m.

1 stop25h 53m

Chicago O'Hare Intl

Thu 4/12

9:53 p.m.-7:50 p.m.

2 stops21h 57m

C$ 487

ReginaChicago

YQR - MDW

YQRMDW

Regina

Wed 10/12

11:40 a.m.-6:18 p.m.

1 stop6h 38m

Chicago Midway

Sat 13/12

6:00 a.m.-6:20 p.m.

2 stops12h 20m

C$ 490

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sun 23/11

8:10 a.m.-7:46 a.m.

2 stops23h 36m

Chicago O'Hare Intl

Sat 29/11

8:22 p.m.-2:38 p.m.

1 stop18h 16m

C$ 529

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 28/11

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

1 stop7h 10m

Chicago O'Hare Intl

Mon 1/12

4:58 p.m.-11:57 p.m.

2 stops30h 59m

C$ 577

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/10

Showing 1-10 of 41 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, September is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 200). Flying from Saskatchewan to Chicago in January is currently the most expensive (average of C$ 741). 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 30 October 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$ 475, WestJet can have you in Chicago from Saskatchewan in 7h. 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 Saskatoon - Chicago Midway or Regina - 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, September is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 200). Flying from Saskatchewan to Chicago in January is currently the most expensive (average of C$ 741). 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

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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 Midway flights
Pearson Intl to Midway flights
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Toronto Island to O'Hare Intl flights
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Halifax to O'Hare Intl flights
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Halifax to Midway flights
Calgary to Midway flights
Edmonton to Midway flights
Edmonton to St. Louis flights
Saskatoon to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Vancouver Intl to St. Louis flights
Saskatoon to Midway flights
Québec City to Midway flights
Hamilton to O'Hare Intl flights
Fort McMurray to O'Hare Intl flights
Kelowna to O'Hare Intl flights
London to O'Hare Intl flights
Regina to O'Hare Intl flights
Ottawa to St. Louis flights
Victoria to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights
St. John's to O'Hare Intl flights
Kelowna to Midway flights
Pearson Intl to Bloomington flights
Calgary to St. Louis flights
Halifax to St. Louis flights
Moncton to O'Hare Intl flights
Victoria to St. Louis flights
Sudbury to O'Hare Intl flights
Québec City to St. Louis flights
Pearson Intl to Moline flights
Pearson Intl to Champaign flights
Vancouver Intl to Peoria flights
Grande Prairie to O'Hare Intl flights
St John to O'Hare Intl 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 30 October 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 380AverageC$ 781FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 411AverageC$ 1,152FlexibilityNo 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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