Find flights
When to book
Airlines
FAQs

Cheap flights from Saskatoon to Chicago from C$ 151

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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
16 Oct — 23 Oct1
1 adult
1 adult, Economy

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 16 September 2025.

Round-trip from

C$ 293

One-way from

C$ 151

Popular in

February

Cheapest in

September

Average price

C$ 424
WestJet
  • WestJet
  • 29/1-2/2
  • 2 total stops
  • 42h 53m total
  • Saskatoon to Chicago
Search Deals
WestJet
  • WestJet
  • 5/12
  • 1 total stop
  • 7h 10m total
  • Saskatoon to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 73 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Saskatoon to Chicago

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 16 September 2025.

Thu 2/108:45 p.m.YXE - ORD
1 stop18h 58mWestJet
Mon 6/105:30 p.m.ORD - YXE
1 stop17h 54mWestJet
Deal found 15/9C$ 326
Fri 5/126:25 a.m.YXE - ORD
1 stop7h 10mDelta
Sun 7/126:00 a.m.ORD - YXE
1 stop8h 38mDelta
Deal found 14/9C$ 369
Sat 8/1111:30 a.m.YXE - ORD
2 stops24h 07mUnited Airlines
Sat 15/116:28 p.m.ORD - YXE
1 stop16h 07mUnited Airlines
Deal found 15/9C$ 482
Thu 2/105:20 a.m.YXE - MDW
2 stops11h 15mDelta
Mon 6/101:48 p.m.MDW - YXE
1 stop8h 36mDelta
Deal found 15/9C$ 635
Fri 5/127:00 a.m.YXE - MDW
2 stops11h 00mDelta
Sun 7/121:14 p.m.MDW - YXE
2 stops12h 19mDelta
Deal found 14/9C$ 921
Sat 8/114:30 p.m.YXE - MDW
2 stops17h 22mWestJet
Sat 15/1111:05 a.m.MDW - YXE
2 stops14h 28mWestJet
Deal found 14/9C$ 968
Thu 2/105:20 a.m.YXE - MDW
2 stops11h 15mWestJet
Mon 6/109:20 a.m.MDW - YXE
2 stops11h 27mWestJet
Deal found 15/9C$ 996
Sat 8/116:25 a.m.YXE - MDW
2 stops32h 55mMultiple Airlines
Sat 15/119:41 a.m.MDW - YXE
3 stops16h 08mMultiple Airlines
Deal found 15/9C$ 1,352
Wed 17/93:15 p.m.YXE - MDW
2 stops31h 05mMultiple Airlines
Fri 19/99:35 a.m.MDW - YXE
1 stop15h 44mMultiple Airlines
Deal found 13/9C$ 1,482

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 16 September 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.-9:46 a.m.

1 stop19h 26m

C$ 293

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 2/10

8:45 p.m.-4:43 p.m.

1 stop18h 58m

Chicago O'Hare Intl

Mon 6/10

5:30 p.m.-10:24 a.m.

1 stop17h 54m

C$ 326

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 5/12

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

1 stop7h 10m

Chicago O'Hare Intl

Sun 7/12

6:00 a.m.-2:38 p.m.

1 stop8h 38m

C$ 369

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sun 25/1

8:10 a.m.-6:08 p.m.

1 stop9h 58m

Chicago Midway

Tue 10/3

9:20 a.m.-1:37 p.m.

1 stop5h 17m

C$ 544

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Thu 2/10

5:20 a.m.-5:35 p.m.

2 stops11h 15m

Chicago Midway

Mon 6/10

1:48 p.m.-9:24 p.m.

1 stop8h 36m

C$ 635

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Fri 5/12

7:00 a.m.-6:00 p.m.

2 stops11h 00m

Chicago Midway

Sun 7/12

1:14 p.m.-1:33 a.m.

2 stops12h 19m

C$ 921

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sat 8/11

4:30 p.m.-9:52 a.m.

2 stops17h 22m

Chicago Midway

Sat 15/11

11:05 a.m.-1:33 a.m.

2 stops14h 28m

C$ 968

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Thu 2/10

5:20 a.m.-5:35 p.m.

2 stops11h 15m

Chicago Midway

Mon 6/10

9:20 a.m.-7:47 p.m.

2 stops11h 27m

C$ 996

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 5/12

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

1 stop7h 10m

C$ 151

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 3/10

8:55 a.m.-12:39 p.m.

1 stop26h 44m

C$ 192

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/9

Showing 1-10 of 26 results
1
2
3

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 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 16 September 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 14% on your trip compared to booking a flight at noon.

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 55% 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$ 530.

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 45m.

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 16 September 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
3,093 reviews
Check prices

Boarding

7.4

Overall

7.2

Crew

7.9

Entertainment

6.1

Food

6.2

Comfort

7.1

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
3,093 reviews
WestJet
7.2
Good
3,093 reviews
Check prices

Boarding

7.4

Overall

7.2

Crew

7.9

Entertainment

6.1

Food

6.2

Comfort

7.1

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
10,000 reviews
WestJet
7.2
Good
3,093 reviews
Check prices

Boarding

7.4

Overall

7.2

Crew

7.9

Entertainment

6.1

Food

6.2

Comfort

7.1

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 Delta fly from Saskatoon to Chicago in about 9h 58m. The time it takes to get you to your destination can typically vary by up to 5h 52m. Airlines will cover a distance of 1833 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$ 376, 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$ 411. You may be able to fly from Saskatoon to Chicago for 45% 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, January is the cheapest month in which you can book a flight from Saskatoon to Chicago (average of C$ 261). Flying from Saskatoon to Chicago in March is currently the most expensive (average of C$ 348). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Regina to O'Hare Intl flights
Saskatoon to Midway 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 16 September 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 376AverageC$ 773FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 411AverageC$ 805FlexibilityNo 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.