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Cheap flights from Saskatchewan to Chicago from C$ 329

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 15/5. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
5 Apr — 12 Apr1
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 31 March 2025.

Round-trip from

C$ 354

One-way from

C$ 329

Popular in

February

Cheapest in

September

Average price

C$ 806
Air Canada
  • Air Canada
  • 14/5-21/5
  • 2 total stops
  • 21h 46m total
  • Saskatchewan to Chicago
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15/5
  • 15/5
  • 2 total stops
  • 15h 32m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 100 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 31 March 2025.

Wed 14/52:25 p.m.YQR - ORD
1 stop6h 41mAir Canada
Wed 21/58:25 p.m.ORD - YQR
1 stop15h 05mAir Canada
Deal found 30/3C$ 354
Tue 15/77:00 a.m.YXE - ORD
1 stop8h 44mWestJet
Fri 18/75:30 p.m.ORD - YXE
1 stop8h 24mWestJet
Deal found 30/3C$ 406
Tue 13/57:55 a.m.YXE - ORD
1 stop7h 49mDelta
Tue 20/56:24 a.m.ORD - YXE
2 stops11h 54mDelta
Deal found 31/3C$ 458
Thu 15/511:45 a.m.YQR - ORD
2 stops22h 51mMultiple Airlines
Thu 22/56:18 p.m.ORD - YQR
1 stop23h 12mMultiple Airlines
Deal found 31/3C$ 537
Thu 15/56:00 a.m.YQR - MDW
2 stops11h 45mDelta
Thu 22/56:00 a.m.MDW - YQR
2 stops11h 30mDelta
Deal found 31/3C$ 697
Wed 14/57:45 p.m.YXE - ORD
1 stop11h 18mUnited Airlines
Wed 21/54:00 p.m.ORD - YXE
1 stop8h 57mUnited Airlines
Deal found 31/3C$ 714
Thu 15/55:45 a.m.YQR - MDW
2 stops11h 00mMultiple Airlines
Thu 22/59:40 a.m.MDW - YQR
3 stops16h 27mMultiple Airlines
Deal found 31/3C$ 1,242

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 31 March 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

Wed 14/5

2:25 p.m.-10:06 p.m.

1 stop6h 41m

Chicago O'Hare Intl

Wed 21/5

8:25 p.m.-10:30 a.m.

1 stop15h 05m

C$ 354

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 15/7

7:00 a.m.-4:44 p.m.

1 stop8h 44m

Chicago O'Hare Intl

Fri 18/7

5:30 p.m.-12:54 a.m.

1 stop8h 24m

C$ 406

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 13/5

7:55 a.m.-4:44 p.m.

1 stop7h 49m

Chicago O'Hare Intl

Tue 20/5

6:24 a.m.-5:18 p.m.

2 stops11h 54m

C$ 458

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 15/5

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

2 stops22h 51m

Chicago O'Hare Intl

Thu 22/5

6:18 p.m.-4:30 p.m.

1 stop23h 12m

C$ 537

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 15/5

6:00 a.m.-6:45 p.m.

2 stops11h 45m

Chicago Midway

Thu 22/5

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

2 stops11h 30m

C$ 697

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Wed 14/5

7:45 p.m.-8:03 a.m.

1 stop11h 18m

Chicago O'Hare Intl

Wed 21/5

4:00 p.m.-11:57 p.m.

1 stop8h 57m

C$ 714

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 15/5

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

2 stops11h 00m

Chicago Midway

Thu 22/5

9:40 a.m.-1:07 a.m.

3 stops16h 27m

C$ 1,242

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 15/5

7:00 a.m.-11:32 p.m.

2 stops15h 32m

C$ 329

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 15/5

7:00 a.m.-4:44 p.m.

1 stop8h 44m

C$ 437

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/3

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 31 March 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 31 March 2025.
Delta
8.0
Very good
7,899 reviews
Check prices

Crew

8.5

Comfort

8.0

Food

7.3

Boarding

8.2

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
7,899 reviews
Delta
8.0
Very good
7,899 reviews
Check prices

Crew

8.5

Comfort

8.0

Food

7.3

Boarding

8.2

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
United Airlines
7.4
Good
8,614 reviews
Delta
8.0
Very good
7,899 reviews
Check prices

Crew

8.5

Comfort

8.0

Food

7.3

Boarding

8.2

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
2,789 reviews
Delta
8.0
Very good
7,899 reviews
Check prices

Crew

8.5

Comfort

8.0

Food

7.3

Boarding

8.2

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
9,004 reviews
Delta
8.0
Very good
7,899 reviews
Check prices

Crew

8.5

Comfort

8.0

Food

7.3

Boarding

8.2

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 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, 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 31 March 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 325AverageC$ 683FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 390AverageC$ 627FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 512AverageC$ 609FlexibilityNo 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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