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Cheap flights from Saskatoon to Chicago from C$ 154

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 14/12. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Saskatoon to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Saskatoon to Chicago
Explore the most affordable flight options available from Saskatoon to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 October 2025.

Mon 24/116:25 a.m.YXE - ORD
1 stop7h 10mMultiple Airlines
Sun 30/116:13 a.m.ORD - YXE
1 stop8h 25mMultiple Airlines
Deal found 29/10C$ 406
Sun 23/118:10 a.m.YXE - ORD
1 stop26h 29mMultiple Airlines
Sat 29/118:22 p.m.ORD - YXE
1 stop18h 16mMultiple Airlines
Deal found 28/10C$ 458
Thu 27/118:10 a.m.YXE - ORD
1 stop25h 53mMultiple Airlines
Thu 4/129:53 p.m.ORD - YXE
2 stops21h 57mMultiple Airlines
Deal found 30/10C$ 487
Thu 18/128:10 a.m.YXE - ORD
1 stop10h 58mMultiple Airlines
Tue 23/126:05 p.m.ORD - YXE
2 stops44h 33mMultiple Airlines
Deal found 29/10C$ 505
Sun 23/118:10 a.m.YXE - ORD
1 stop26h 29mMultiple Airlines
Sun 30/119:18 a.m.ORD - YXE
1 stop5h 20mMultiple Airlines
Deal found 29/10C$ 521
Fri 28/116:25 a.m.YXE - ORD
1 stop7h 10mMultiple Airlines
Mon 1/128:22 p.m.ORD - YXE
1 stop18h 16mMultiple Airlines
Deal found 29/10C$ 561
Thu 27/118:10 a.m.YXE - MDW
2 stops14h 33mMultiple Airlines
Thu 4/1211:00 a.m.MDW - YXE
1 stop14h 33mMultiple Airlines
Deal found 30/10C$ 564
Sun 23/118:10 a.m.YXE - MDW
2 stops16h 03mMultiple Airlines
Sat 29/1112:45 p.m.MDW - YXE
1 stop12h 48mMultiple Airlines
Deal found 28/10C$ 580
Sat 22/117:00 a.m.YXE - MDW
1 stop27h 05mMultiple Airlines
Sat 29/1112:45 p.m.MDW - YXE
1 stop12h 48mMultiple Airlines
Deal found 28/10C$ 588
Thu 27/117:00 a.m.YXE - MDW
3 stops35h 18mWestJet
Thu 4/127:02 p.m.MDW - YXE
2 stops30h 31mWestJet
Deal found 30/10C$ 765
Wed 10/124:45 p.m.YXE - MDW
2 stops17h 20mMultiple Airlines
Sat 13/121:50 p.m.MDW - YXE
3 stops26h 09mMultiple Airlines
Deal found 29/10C$ 771
Wed 10/124:45 p.m.YXE - MDW
3 stops25h 33mWestJet
Sat 13/129:59 a.m.MDW - YXE
3 stops30h 00mWestJet
Deal found 29/10C$ 839

Cheap flight deals from Saskatoon to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Saskatoon (YXE) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 30 October 2025.

Round-trip from

C$ 406

One-way from

C$ 154

Popular in

February

Cheapest in

January

Average price

C$ 533
24/11-30/11
  • 24/11-30/11
  • 2 total stops
  • 15h 35m total
  • Saskatoon to Chicago
Search Deals
14/12
  • 14/12
  • 1 total stop
  • 26h 06m total
  • Saskatoon to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Saskatoon 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 30 October 2025.
Use the filters below to find and compare flights from Saskatoon to Chicago that are best for you.

Fly from

Saskatoon

Fly to

Chicago

Route

Depart

Return

Price

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 29/1

9:45 p.m.-1:35 p.m.

1 stop15h 50m

Chicago O'Hare Intl

Mon 2/2

2:20 p.m.-3:58 p.m.

1 stop25h 38m

C$ 415

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Mon 24/11

6:25 a.m.-1:35 p.m.

1 stop7h 10m

Chicago O'Hare Intl

Sun 30/11

6:13 a.m.-2:38 p.m.

1 stop8h 25m

C$ 434

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 28/4

5:00 a.m.-1:00 p.m.

1 stop7h 00m

Chicago O'Hare Intl

Sat 2/5

3:45 p.m.-11:56 p.m.

1 stop9h 11m

C$ 475

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 27/11

8:10 a.m.-10:03 a.m.

1 stop25h 53m

Chicago O'Hare Intl

Thu 4/12

9:53 p.m.-7:50 p.m.

2 stops21h 57m

C$ 487

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sun 23/11

8:10 a.m.-7:46 a.m.

2 stops23h 36m

Chicago O'Hare Intl

Sat 29/11

8:22 p.m.-2:38 p.m.

1 stop18h 16m

C$ 529

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 28/11

6:25 a.m.-1:35 p.m.

1 stop7h 10m

Chicago O'Hare Intl

Mon 1/12

4:58 p.m.-11:57 p.m.

2 stops30h 59m

C$ 577

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sun 23/11

8:10 a.m.-12:13 a.m.

2 stops16h 03m

Chicago Midway

Sat 29/11

12:45 p.m.-1:33 a.m.

1 stop12h 48m

C$ 580

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sat 22/11

4:35 p.m.-10:05 a.m.

2 stops17h 30m

Chicago Midway

Sat 29/11

12:45 p.m.-1:33 a.m.

1 stop12h 48m

C$ 591

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Wed 10/12

4:45 p.m.-10:05 a.m.

2 stops17h 20m

Chicago Midway

Sat 13/12

9:59 a.m.-1:33 a.m.

2 stops15h 34m

C$ 771

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Thu 27/11

4:45 p.m.-10:05 a.m.

2 stops17h 20m

Chicago Midway

Thu 4/12

7:02 p.m.-1:33 a.m.

2 stops30h 31m

C$ 792

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/10

Showing 1-10 of 23 results
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Best time to book a flight from Saskatoon to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Saskatoon 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 Saskatoon to Chicago

What is the cheapest month to book a flight from Saskatoon to Chicago?

Currently, July is the cheapest month in which you can book a flight from Saskatoon to Chicago (average of C$ 355). Flying from Saskatoon to Chicago in January is currently the most expensive (average of C$ 1,011). 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 YXE to CHI?

Find hourly flight availability from Saskatoon 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 30 October 2025.

A simple way to save on the total cost of your ticket is to fly from Saskatoon to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 87% on your trip compared to booking a flight at noon.

How much does it cost to fly round-trip from Saskatoon to Chicago?

What’s the top layover airport for flights from Saskatoon to Chicago?

Share of one-stop round-trip flights from Saskatoon to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Toronto (YYZ) – chosen by Cheapflights users on 53% of one-stop itineraries from Saskatoon to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Saskatoon to Chicago?

Average round-trip fare for 1-stop flights from Saskatoon to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 536.

What’s the fastest layover option from Saskatoon to Chicago?

Shortest average travel time for 1-stop one-way flights from Saskatoon to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 7h 07m.

Which airport typically offers the quickest layover for flights from Saskatoon to Chicago?

Average layover duration for 1-stop one-way flights from Saskatoon to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 2h 44m.

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 30 October 2025.
See what other customers who have flown with WestJet and Air Canada from Saskatoon to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,152 reviews
Check prices

Food

6.2

Crew

7.9

Comfort

7.1

Overall

7.2

Boarding

7.4

Entertainment

6.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.
WestJet
7.2
Good
3,152 reviews
WestJet
7.2
Good
3,152 reviews
Check prices

Food

6.2

Crew

7.9

Comfort

7.1

Overall

7.2

Boarding

7.4

Entertainment

6.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.
Air Canada
7.1
Good
10,381 reviews
WestJet
7.2
Good
3,152 reviews
Check prices

Food

6.2

Crew

7.9

Comfort

7.1

Overall

7.2

Boarding

7.4

Entertainment

6.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.

Related info for your journey

Find useful and relevant information for your journey from Saskatoon to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Saskatoon to Chicago?

    Located just 4.6 km from the city centre, Saskatoon is the airport most travellers will use when flying to Chicago from Saskatoon. Booking flights from Saskatoon (YXE) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 2 different airlines.

  • How long is the flight from Saskatoon to Chicago?

    Airlines like WestJet and Air Canada fly from Saskatoon to Chicago in about 7h. The time it takes to get you to your destination can typically vary by up to 8h 50m. Airlines will cover a distance of 1809 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What are the cheapest airlines flying from Saskatoon to Chicago round-trip?

    Currently priced at C$ 380, WestJet will fly you from Saskatoon to Chicago and back. In addition to WestJet, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Air Canada for as low as C$ 415. You may be able to fly from Saskatoon to Chicago for 44% less than the average price by searching for these airlines.

  • Can I find deals for flights from Saskatoon to Chicago that include hotel bookings?

    Yes. In addition to deals on Saskatoon to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Saskatoon to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Saskatoon to Chicago.

  • Can I find deals for business class flights from Saskatoon to Chicago?

    Yes. Cheapflights offers flight deals from Saskatoon 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 Saskatoon to Chicago?

    Currently, July is the cheapest month in which you can book a flight from Saskatoon to Chicago (average of C$ 355). Flying from Saskatoon to Chicago in January is currently the most expensive (average of C$ 1,011). 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 Saskatoon to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Saskatoon to O'Hare Intl flights
Saskatoon to Midway flights
Regina to O'Hare Intl flights
Saskatoon to St. Louis flights

Top 2 airlines flying from Saskatoon to Chicago

Discover the top 2 airlines that operate flights from Saskatoon 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 30 October 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 380AverageC$ 781FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 415AverageC$ 814FlexibilityNo 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 Saskatoon to Chicago?

Deals for Saskatoon to Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Saskatoon to Chicago?

Millions of users choose and trust Cheapflights to book the best flight deals from Saskatoon to Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Saskatoon to Chicago with no change fees?

Yes, we can. To see specific flights from Saskatoon to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Saskatoon to Chicago become cheaper?

Not ready to book yet? You can track prices for flights from Saskatoon to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.

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