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Cheap flights from Saskatchewan to Chicago from C$ 186

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 15/4. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
27 Feb — 6 Mar1
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 22 February 2025.

Round-trip from

C$ 422

One-way from

C$ 186

Popular in

November

Cheapest in

September

Average price

C$ 642
24/4-28/4
  • 24/4-28/4
  • 2 total stops
  • 37h 29m total
  • Saskatchewan to Chicago
Search Deals
15/4
  • 15/4
  • 2 total stops
  • 12h 03m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 220 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 22 February 2025.

Thu 24/47:10 a.m.YXE - ORD
1 stop10h 09mMultiple Airlines
Mon 28/47:05 p.m.ORD - YXE
1 stop27h 20mMultiple Airlines
Deal found 21/2C$ 422
Mon 7/46:00 a.m.YXE - ORD
1 stop7h 55mUnited Airlines
Mon 14/44:00 p.m.ORD - YXE
1 stop6h 52mUnited Airlines
Deal found 21/2C$ 436
Thu 24/46:00 a.m.YXE - ORD
2 stops11h 54mAir Canada
Mon 28/48:25 p.m.ORD - YXE
1 stop14h 52mAir Canada
Deal found 21/2C$ 515
Sat 5/48:45 p.m.YQR - ORD
1 stop18h 11mMultiple Airlines
Sat 12/42:58 p.m.ORD - YQR
3 stops34h 58mMultiple Airlines
Deal found 21/2C$ 525
Sun 18/56:55 a.m.YQR - ORD
1 stop8h 49mWestJet
Thu 22/55:30 p.m.ORD - YQR
1 stop24h 58mWestJet
Deal found 20/2C$ 552
Mon 7/44:45 a.m.YXE - MDW
2 stops27h 22mWestJet
Mon 14/41:16 p.m.MDW - YXE
1 stop25h 34mWestJet
Deal found 21/2C$ 701
Fri 28/35:00 a.m.YQR - ORD
2 stops12h 21mDelta
Tue 1/412:15 p.m.ORD - YQR
1 stop5h 21mDelta
Deal found 21/2C$ 704
Sat 5/45:45 a.m.YQR - ORD
1 stop6h 30mAir Canada
Sat 12/44:00 p.m.ORD - YQR
1 stop7h 13mAir Canada
Deal found 21/2C$ 717
Thu 24/44:45 a.m.YXE - ORD
2 stops15h 00mWestJet
Mon 28/45:30 p.m.ORD - YXE
2 stops22h 42mWestJet
Deal found 21/2C$ 732
Sat 5/410:45 a.m.YQR - MDW
1 stop6h 48mDelta
Sat 12/49:23 a.m.MDW - YQR
2 stops8h 13mDelta
Deal found 20/2C$ 811
Fri 28/35:05 p.m.YQR - MDW
2 stops24h 28mWestJet
Tue 1/412:51 p.m.MDW - YQR
2 stops12h 03mWestJet
Deal found 21/2C$ 899
Thu 27/28:10 a.m.YXE - ORD
2 stops10h 15mDelta
Sun 2/36:15 a.m.ORD - YXE
2 stops12h 34mDelta
Deal found 21/2C$ 1,236

Find flights from Saskatchewan to Chicago within your budget

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 22 February 2025.

Fly from

Saskatchewan

Fly to

Chicago

Route

Depart

Return

Price

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 24/4

7:10 a.m.-6:19 p.m.

1 stop10h 09m

Chicago O'Hare Intl

Mon 28/4

7:05 p.m.-9:25 p.m.

1 stop27h 20m

C$ 422

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Mon 7/4

6:00 a.m.-2:55 p.m.

1 stop7h 55m

Chicago O'Hare Intl

Mon 14/4

4:00 p.m.-9:52 p.m.

1 stop6h 52m

C$ 436

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 24/4

6:00 a.m.-6:54 p.m.

2 stops11h 54m

Chicago O'Hare Intl

Mon 28/4

8:25 p.m.-10:17 a.m.

1 stop14h 52m

C$ 515

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 5/4

8:45 p.m.-3:56 p.m.

1 stop18h 11m

Chicago O'Hare Intl

Sat 12/4

2:58 p.m.-12:56 a.m.

3 stops34h 58m

C$ 525

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 18/5

6:55 a.m.-4:44 p.m.

1 stop8h 49m

Chicago O'Hare Intl

Thu 22/5

5:30 p.m.-5:28 p.m.

1 stop24h 58m

C$ 552

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Mon 7/4

4:45 a.m.-9:07 a.m.

2 stops27h 22m

Chicago Midway

Mon 14/4

1:16 p.m.-1:50 p.m.

1 stop25h 34m

C$ 701

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 28/3

5:00 a.m.-6:21 p.m.

2 stops12h 21m

Chicago O'Hare Intl

Tue 1/4

12:15 p.m.-4:36 p.m.

1 stop5h 21m

C$ 704

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 5/4

5:45 a.m.-1:15 p.m.

1 stop6h 30m

Chicago O'Hare Intl

Sat 12/4

4:00 p.m.-10:13 p.m.

1 stop7h 13m

C$ 717

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 24/4

4:45 a.m.-8:45 p.m.

2 stops15h 00m

Chicago O'Hare Intl

Mon 28/4

5:30 p.m.-3:12 p.m.

2 stops22h 42m

C$ 732

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sat 5/4

10:45 a.m.-6:33 p.m.

1 stop6h 48m

Chicago Midway

Sat 12/4

9:23 a.m.-4:36 p.m.

2 stops8h 13m

C$ 811

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/2

Showing 1-10 of 18 results
1
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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.

Travel insights for flights from Saskatchewan to Chicago

Get recent, data-driven insights about flights from Saskatchewan to Chicago including ideal travel times, pricing trends, and more.

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 22 February 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 22 February 2025.
Read through reviews of airlines operating flights from Saskatchewan to Chicago, such as Delta, United Airlines and WestJet. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,203 reviews
Check prices

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

Comfort

8.0

Boarding

8.2

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
8,203 reviews
Delta
8.0
Very good
8,203 reviews
Check prices

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

Comfort

8.0

Boarding

8.2

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
8,754 reviews
Delta
8.0
Very good
8,203 reviews
Check prices

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

Comfort

8.0

Boarding

8.2

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
2,800 reviews
Delta
8.0
Very good
8,203 reviews
Check prices

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

Comfort

8.0

Boarding

8.2

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
8,758 reviews
Delta
8.0
Very good
8,203 reviews
Check prices

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

Comfort

8.0

Boarding

8.2

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 O'Hare Intl or Regina - Chicago Midway.

  • 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

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.
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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 22 February 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 322AverageC$ 633FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 387AverageC$ 667FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 507AverageC$ 604FlexibilityNo cancel feeOn-timeN/A
Search Delta flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Saskatchewan to Chicago?

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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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