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Cheap flights from Saskatchewan to Chicago from C$ 207

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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
26 Dec — 2 Jan1
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 26 November 2025.

Mon 8/1212:15 p.m.YQR - ORD
2 stops9h 25mDelta
Fri 12/126:45 a.m.ORD - YQR
2 stops11h 35mDelta
Deal found 24/11C$ 580
Sun 21/123:25 p.m.YXE - ORD
1 stop16h 38mUnited Airlines
Sat 10/18:00 a.m.ORD - YXE
1 stop6h 35mUnited Airlines
Deal found 24/11C$ 708
Tue 16/128:10 a.m.YXE - ORD
1 stop6h 49mDelta
Sat 20/127:05 p.m.ORD - YXE
1 stop19h 33mDelta
Deal found 26/11C$ 800
Mon 8/126:10 a.m.YQR - ORD
1 stop7h 25mWestJet
Fri 12/122:20 p.m.ORD - YQR
1 stop6h 55mWestJet
Deal found 23/11C$ 810
Sun 21/128:10 a.m.YXE - ORD
2 stops12h 26mDelta
Sat 10/111:05 a.m.ORD - YXE
2 stops14h 28mDelta
Deal found 25/11C$ 816
Tue 16/127:00 a.m.YXE - ORD
2 stops14h 40mWestJet
Sat 20/127:00 a.m.ORD - YXE
2 stops18h 33mWestJet
Deal found 24/11C$ 859
Mon 1/1210:45 a.m.YQR - ORD
1 stop8h 08mUnited Airlines
Sat 20/121:48 p.m.ORD - YQR
1 stop9h 03mUnited Airlines
Deal found 24/11C$ 945
Wed 24/1211:40 a.m.YQR - MDW
1 stop5h 39mDelta
Sun 28/126:08 p.m.MDW - YQR
2 stops24h 12mDelta
Deal found 24/11C$ 978
Wed 24/1210:53 a.m.YQR - ORD
1 stop13h 06mUnited Airlines
Sun 28/128:15 p.m.ORD - YQR
1 stop14h 24mUnited Airlines
Deal found 24/11C$ 1,043
Wed 24/1211:40 a.m.YQR - MDW
1 stop5h 39mWestJet
Sun 28/125:59 p.m.MDW - YQR
1 stop24h 21mWestJet
Deal found 24/11C$ 1,045
Mon 1/1211:40 a.m.YQR - ORD
1 stop27h 19mWestJet
Sat 20/126:35 a.m.ORD - YQR
1 stop11h 45mWestJet
Deal found 25/11C$ 1,102
Wed 24/1212:15 p.m.YQR - ORD
2 stops33h 19mWestJet
Sun 28/124:01 p.m.ORD - YQR
2 stops42h 39mWestJet
Deal found 24/11C$ 1,140

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 26 November 2025.

Round-trip from

C$ 316

One-way from

C$ 207

Popular in

February

Cheapest in

January

Average price

C$ 689
WestJet
  • WestJet
  • 16/4-17/6
  • 2 total stops
  • 29h 57m total
  • Saskatchewan to Chicago
Search Deals
9/1
  • 9/1
  • 2 total stops
  • 25h 16m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 41 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 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 16/4

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

1 stop23h 25m

Chicago O'Hare Intl

Wed 17/6

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

1 stop6h 32m

C$ 316

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 29/1

11:55 a.m.-1:35 p.m.

1 stop25h 40m

Chicago O'Hare Intl

Mon 2/2

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

1 stop6h 38m

C$ 356

ReginaChicago

YQR - MDW

YQRMDW

Regina

Mon 26/1

11:45 a.m.-6:36 p.m.

1 stop6h 51m

Chicago Midway

Fri 30/1

9:50 a.m.-6:17 p.m.

1 stop8h 27m

C$ 470

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sun 25/1

6:00 a.m.-3:10 p.m.

1 stop9h 10m

Chicago O'Hare Intl

Thu 29/1

8:45 p.m.-10:35 a.m.

1 stop13h 50m

C$ 573

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 8/12

11:40 a.m.-7:55 p.m.

1 stop8h 15m

Chicago O'Hare Intl

Fri 12/12

8:55 a.m.-6:20 p.m.

2 stops9h 25m

C$ 580

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Mon 26/1

7:00 a.m.-6:36 p.m.

2 stops35h 36m

Chicago Midway

Thu 29/1

9:50 a.m.-2:38 p.m.

1 stop4h 48m

C$ 601

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 16/4

5:00 a.m.-6:33 p.m.

2 stops12h 33m

Chicago O'Hare Intl

Wed 17/6

8:40 a.m.-6:13 p.m.

2 stops10h 33m

C$ 736

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 8/12

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

1 stop7h 25m

Chicago O'Hare Intl

Fri 12/12

2:20 p.m.-9:15 p.m.

1 stop6h 55m

C$ 810

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 16/4

11:45 a.m.-6:05 p.m.

1 stop5h 20m

Chicago Midway

Wed 17/6

9:20 a.m.-4:30 p.m.

1 stop8h 10m

C$ 828

ReginaChicago

YQR - MDW

YQRMDW

Regina

Wed 24/12

11:40 a.m.-5:19 p.m.

1 stop5h 39m

Chicago Midway

Sun 28/12

6:08 p.m.-6:20 p.m.

2 stops24h 12m

C$ 978

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/11

Showing 1-10 of 29 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, December is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 179). Flying from Saskatchewan to Chicago in January is currently the most expensive (average of C$ 749). 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 26 November 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$ 470, WestJet can have you in Chicago from Saskatchewan in 6h 51m. 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 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, December is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 179). Flying from Saskatchewan to Chicago in January is currently the most expensive (average of C$ 749). 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 Midway flights
Pearson Intl to Midway flights
Vancouver Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Calgary to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Vancouver Intl to Midway flights
Pearson Intl to St. Louis flights
Winnipeg to O'Hare Intl flights
Halifax to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Ottawa to Midway flights
Calgary to Midway flights
Halifax to Midway flights
Vancouver Intl to St. Louis flights
Québec City to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Edmonton to Midway flights
Québec City to Midway flights
Kelowna to O'Hare Intl flights
Kelowna to Midway flights
Saskatoon to St. Louis flights
Halifax to St. Louis flights
Edmonton to St. Louis flights
Québec City to St. Louis flights
Hamilton to O'Hare Intl flights
Victoria to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
St. John's to O'Hare Intl flights
Vancouver Intl to Peoria flights
Regina to O'Hare Intl flights
Calgary to St. Louis flights
London to O'Hare Intl flights
Pearson Intl to Moline flights
Ottawa to St. Louis flights
Pearson Intl to Peoria flights
Victoria to St. Louis flights
Saskatoon to Midway flights
Sudbury to O'Hare Intl flights
Fort McMurray to O'Hare Intl flights
St John to O'Hare Intl flights
Grande Prairie 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 26 November 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 179AverageC$ 483FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 415AverageC$ 1,201FlexibilityNo 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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