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Cheap flights from Saskatchewan to Chicago from C$ 248

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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
4 May — 11 May1
1 adult

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 29 April 2025.

Round-trip from

C$ 563

One-way from

C$ 248

Popular in

February

Cheapest in

September

Average price

C$ 644
14/5-18/5
  • 14/5-18/5
  • 2 total stops
  • 40h 04m total
  • Saskatchewan to Chicago
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Air Canada
  • Air Canada
  • 12/6
  • 1 total stop
  • 11h 49m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 81 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 37 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
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Find flight deals from Saskatchewan to Chicago

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 29 April 2025.

Wed 14/53:15 p.m.YXE - ORD
1 stop26h 54mMultiple Airlines
Sun 18/59:15 a.m.ORD - YXE
1 stop13h 10mMultiple Airlines
Deal found 27/4C$ 563
Wed 7/56:00 a.m.YXE - MDW
2 stops11h 45mDelta
Sun 11/51:55 p.m.MDW - YXE
1 stop8h 30mDelta
Deal found 27/4C$ 736
Wed 14/56:00 a.m.YXE - ORD
2 stops9h 30mWestJet
Sun 18/56:24 a.m.ORD - YXE
2 stops14h 17mWestJet
Deal found 27/4C$ 942
Wed 7/58:45 p.m.YXE - MDW
2 stops23h 43mWestJet
Sun 11/51:55 p.m.MDW - YXE
2 stops11h 59mWestJet
Deal found 27/4C$ 1,060

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 29 April 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

Wed 14/5

3:15 p.m.-7:09 p.m.

1 stop26h 54m

Chicago O'Hare Intl

Sun 18/5

9:15 a.m.-9:25 p.m.

1 stop13h 10m

C$ 563

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Wed 14/5

6:00 a.m.-4:30 p.m.

2 stops9h 30m

Chicago O'Hare Intl

Sun 18/5

6:24 a.m.-7:41 p.m.

2 stops14h 17m

C$ 942

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Wed 14/5

5:40 a.m.-6:45 p.m.

2 stops12h 05m

Chicago Midway

Sun 18/5

1:08 p.m.-10:44 p.m.

2 stops10h 36m

C$ 1,492

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 12/6

7:10 p.m.-7:59 a.m.

1 stop11h 49m

C$ 248

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 12/6

8:35 p.m.-12:14 a.m.

2 stops26h 39m

C$ 273

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 12/6

10:15 a.m.-5:40 p.m.

1 stop6h 25m

C$ 273

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 12/6

5:45 a.m.-8:17 p.m.

3 stops13h 32m

C$ 726

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/4

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, January is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 261). Flying from Saskatchewan to Chicago in March is currently the most expensive (average of C$ 355). 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 29 April 2025.

When flying from Saskatchewan to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 29 April 2025.
Delta
8.0
Very good
7,929 reviews
Check prices

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,929 reviews
Delta
8.0
Very good
7,929 reviews
Check prices

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
WestJet
7.2
Good
2,823 reviews
Delta
8.0
Very good
7,929 reviews
Check prices

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air Canada
7.0
Good
9,240 reviews
Delta
8.0
Very good
7,929 reviews
Check prices

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • 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, January is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 261). Flying from Saskatchewan to Chicago in March is currently the most expensive (average of C$ 355). 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.
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Top 3 airlines flying from Saskatchewan to Chicago

Discover the top 3 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 29 April 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 315AverageC$ 617FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 378AverageC$ 672FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 466AverageC$ 553FlexibilityNo cancel feeOn-timeN/A
Search Delta flights

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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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