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Cheap flights from Saskatchewan to Chicago from C$ 179

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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
29 Apr — 6 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 24 April 2025.

Round-trip from

C$ 309

One-way from

C$ 179

Popular in

February

Cheapest in

September

Average price

C$ 644
Air Canada
  • Air Canada
  • 16/6-19/6
  • 2 total stops
  • 27h 01m total
  • Saskatchewan to Chicago
Search Deals
WestJet
  • WestJet
  • 8/5
  • 1 total stop
  • 24h 19m total
  • Saskatchewan to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 36 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 24 April 2025.

Mon 16/69:45 a.m.YQR - ORD
1 stop11h 56mMultiple Airlines
Thu 19/68:25 p.m.ORD - YQR
1 stop15h 05mMultiple Airlines
Deal found 24/4C$ 309
Thu 18/96:00 a.m.YXE - ORD
1 stop8h 04mAir Canada
Mon 22/93:50 p.m.ORD - YXE
1 stop9h 02mAir Canada
Deal found 23/4C$ 364
Mon 26/510:15 a.m.YQR - MDW
1 stop6h 30mDelta
Fri 30/59:20 a.m.MDW - YQR
1 stop8h 10mDelta
Deal found 22/4C$ 395
Thu 18/97:00 a.m.YXE - ORD
1 stop8h 43mWestJet
Mon 22/95:30 p.m.ORD - YXE
2 stops15h 47mWestJet
Deal found 23/4C$ 410
Tue 13/58:35 a.m.YQR - ORD
1 stop7h 09mWestJet
Sun 18/55:30 p.m.ORD - YQR
1 stop8h 37mWestJet
Deal found 23/4C$ 478
Thu 5/611:45 a.m.YXE - ORD
1 stop6h 45mMultiple Airlines
Mon 9/66:15 p.m.ORD - YXE
2 stops17h 32mMultiple Airlines
Deal found 24/4C$ 544
Thu 5/66:00 a.m.YQR - MDW
3 stops31h 03mMultiple Airlines
Thu 12/69:40 a.m.MDW - YQR
3 stops16h 27mMultiple Airlines
Deal found 22/4C$ 713
Thu 5/68:45 p.m.YXE - MDW
2 stops23h 42mWestJet
Mon 9/67:21 p.m.MDW - YXE
2 stops23h 42mWestJet
Deal found 24/4C$ 852
Mon 23/69:45 a.m.YQR - ORD
1 stop7h 40mUnited Airlines
Mon 23/68:25 p.m.ORD - YQR
1 stop15h 05mUnited Airlines
Deal found 23/4C$ 856
Sun 4/510:15 a.m.YQR - MDW
1 stop6h 04mWestJet
Fri 9/59:20 a.m.MDW - YQR
1 stop8h 10mWestJet
Deal found 22/4C$ 949

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 24 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

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 16/6

9:45 a.m.-10:41 p.m.

1 stop11h 56m

Chicago O'Hare Intl

Thu 19/6

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

1 stop15h 05m

C$ 309

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 18/9

6:00 a.m.-3:04 p.m.

1 stop8h 04m

Chicago O'Hare Intl

Mon 22/9

3:50 p.m.-11:52 p.m.

1 stop9h 02m

C$ 364

ReginaChicago

YQR - MDW

YQRMDW

Regina

Mon 26/5

10:15 a.m.-5:45 p.m.

1 stop6h 30m

Chicago Midway

Fri 30/5

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

1 stop8h 10m

C$ 395

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 18/9

7:00 a.m.-4:43 p.m.

1 stop8h 43m

Chicago O'Hare Intl

Mon 22/9

5:30 p.m.-8:17 a.m.

2 stops15h 47m

C$ 410

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 13/5

8:35 a.m.-4:44 p.m.

1 stop7h 09m

Chicago O'Hare Intl

Sun 18/5

5:30 p.m.-1:07 a.m.

1 stop8h 37m

C$ 478

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 5/6

11:45 a.m.-7:30 p.m.

1 stop6h 45m

Chicago O'Hare Intl

Mon 9/6

6:15 p.m.-10:47 a.m.

2 stops17h 32m

C$ 544

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 5/6

6:00 a.m.-2:03 p.m.

3 stops31h 03m

Chicago Midway

Thu 12/6

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

3 stops16h 27m

C$ 713

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Thu 5/6

8:45 p.m.-9:27 p.m.

2 stops23h 42m

Chicago Midway

Mon 9/6

7:21 p.m.-6:03 p.m.

2 stops23h 42m

C$ 852

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 23/6

9:45 a.m.-6:25 p.m.

1 stop7h 40m

Chicago O'Hare Intl

Mon 23/6

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

1 stop15h 05m

C$ 856

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sun 4/5

10:15 a.m.-5:19 p.m.

1 stop6h 04m

Chicago Midway

Fri 9/5

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

1 stop8h 10m

C$ 949

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/4

Showing 1-10 of 21 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, 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 24 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 24 April 2025.
Delta
8.0
Very good
7,920 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

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
7,920 reviews
Delta
8.0
Very good
7,920 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

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
8,685 reviews
Delta
8.0
Very good
7,920 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

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
2,816 reviews
Delta
8.0
Very good
7,920 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

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
9,195 reviews
Delta
8.0
Very good
7,920 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

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 cheapest airlines to fly from Saskatchewan to Chicago one-way?

    The cheapest airlines for a one-way flight from Saskatchewan to Chicago are WestJet (C$ 179), Air Canada (C$ 208), and Delta (C$ 222).

  • What are the most popular routes from Saskatchewan to Chicago?

    The most popular route from Saskatchewan to Chicago is Saskatoon - Chicago Midway. You may also consider Saskatoon - Chicago O'Hare Intl 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

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 24 April 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 314AverageC$ 617FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 377AverageC$ 654FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 465AverageC$ 552FlexibilityNo cancel feeOn-timeN/A
Search Delta flights

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

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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.

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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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