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Cheap flights from Saskatoon to Chicago from C$ 235

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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
YXE — CHI
20 Jul — 27 Jul1
1 adult
1 adult, Economy, 0 bags

Cheap 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 20 June 2026.

Sun 4/108:50 a.m.
YXE
-
ORD
1 stop6h 50m
WestJet
Sun 11/105:30 p.m.
ORD
-
YXE
1 stop6h 40m
WestJet
Deal found 19/6C$ 413
Tue 11/87:00 a.m.
YXE
-
ORD
1 stop8h 40m
WestJet
Tue 18/85:30 p.m.
ORD
-
YXE
1 stop8h 30m
WestJet
Deal found 18/6C$ 483
Tue 14/74:15 p.m.
YXE
-
ORD
2 stops23h 25m
WestJet
Mon 20/75:30 p.m.
ORD
-
YXE
1 stop8h 30m
WestJet
Deal found 20/6C$ 511
Sun 22/118:10 a.m.
YXE
-
ORD
1 stop6h 47m
Delta
Tue 24/116:00 a.m.
ORD
-
YXE
1 stop8h 38m
Delta
Deal found 16/6C$ 531
Sun 22/118:10 a.m.
YXE
-
MDW
1 stop24h 39m
Delta
Tue 24/119:55 a.m.
MDW
-
YXE
1 stop4h 43m
Delta
Deal found 16/6C$ 705
Fri 24/71:20 p.m.
YXE
-
MDW
1 stop19h 20m
Multiple Airlines
Sun 2/810:20 a.m.
MDW
-
YXE
2 stops11h 55m
Multiple Airlines
Deal found 18/6C$ 753
Wed 24/61:20 p.m.
YXE
-
MDW
1 stop19h 20m
Multiple Airlines
Wed 1/73:20 p.m.
MDW
-
YXE
1 stop10h 15m
Multiple Airlines
Deal found 17/6C$ 814
Mon 24/86:00 a.m.
YXE
-
MDW
2 stops11h 33m
Delta
Sat 29/81:25 p.m.
MDW
-
YXE
2 stops10h 45m
Delta
Deal found 20/6C$ 1,004

Find 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 20 June 2026.

Round-trip from

C$ 413

One-way from

C$ 235
WestJet
  • WestJet
  • 4/10-11/10
  • 2 total stops
  • 13h 30m total
  • Saskatoon to Chicago
Search Deals
WestJet
  • WestJet
  • 11/10
  • 1 total stop
  • 8h 40m total
  • Saskatoon to Chicago
Search Deals

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 20 June 2026.
Use the filters below to find and compare flights from Saskatoon to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sun 4/10

8:50 a.m.-4:40 p.m.

1 stop6h 50m

Chicago O'Hare Intl

Sun 11/10

5:30 p.m.-11:10 p.m.

1 stop6h 40m

C$ 413

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 14/7

8:55 p.m.-4:40 p.m.

1 stop18h 45m

Chicago O'Hare Intl

Mon 20/7

5:30 p.m.-11:10 p.m.

1 stop6h 40m

C$ 528

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sun 22/11

8:10 a.m.-2:57 p.m.

1 stop6h 47m

Chicago O'Hare Intl

Tue 24/11

6:00 a.m.-6:50 p.m.

2 stops12h 50m

C$ 589

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 25/8

1:20 p.m.-9:47 p.m.

2 stops7h 27m

Chicago O'Hare Intl

Sat 29/8

11:22 a.m.-1:00 a.m.

2 stops14h 38m

C$ 626
Quickest round-trip

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 16/7

3:10 p.m.-9:52 p.m.

1 stop5h 42m

Chicago O'Hare Intl

Mon 20/7

5:30 p.m.-11:10 p.m.

1 stop6h 40m

C$ 626

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 16/7

3:10 p.m.-9:52 p.m.

1 stop5h 42m

Chicago O'Hare Intl

Thu 23/7

5:30 p.m.-11:10 p.m.

1 stop6h 40m

C$ 631

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Sun 22/11

8:10 a.m.-8:49 a.m.

1 stop24h 39m

Chicago Midway

Tue 24/11

9:55 a.m.-2:38 p.m.

1 stop4h 43m

C$ 705

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Mon 24/8

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Sat 29/8

2:41 p.m.-6:05 p.m.

2 stops28h 24m

C$ 739

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sat 29/8

6:00 a.m.-1:22 p.m.

1 stop6h 22m

Chicago O'Hare Intl

Sat 29/8

10:00 p.m.-4:17 p.m.

2 stops19h 17m

C$ 742

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Fri 24/7

1:20 p.m.-9:40 a.m.

1 stop19h 20m

Chicago Midway

Sun 2/8

10:20 a.m.-9:15 p.m.

2 stops11h 55m

C$ 753

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/6

Showing 1-10 of 25 resultsSorted by cheapest first
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’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.

Calgary (YYC) – chosen by Cheapflights users on 61% 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$ 388.

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 Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 7h 27m.

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 Calgary (YYC) offer the fastest connection on this route, with an average layover time of 2h 29m.

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 20 June 2026.
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
3,375 reviews
Check prices

Overall

7.2

Food

6.2

Crew

7.9

Comfort

7.0

Entertainment

6.1

Boarding

7.4

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
3,375 reviews
WestJet
7.2
Good
3,375 reviews
Check prices

Overall

7.2

Food

6.2

Crew

7.9

Comfort

7.0

Entertainment

6.1

Boarding

7.4

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
11,226 reviews
WestJet
7.2
Good
3,375 reviews
Check prices

Overall

7.2

Food

6.2

Crew

7.9

Comfort

7.0

Entertainment

6.1

Boarding

7.4

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 1 airline.

  • How long is the flight from Saskatoon to Chicago?

    Airlines like WestJet and Delta fly from Saskatoon to Chicago in about 6h 47m. The time it takes to get you to your destination can typically vary by up to 03m. 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 is the cheapest airline to fly from Saskatoon to Chicago round-trip?

    Currently priced at C$ 179, WestJet will fly you from Saskatoon to Chicago and back. In addition to WestJet, many other airlines offer competitively priced options for your trip.

  • 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.

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
Regina to O'Hare Intl flights
Saskatoon to Midway flights
Saskatoon to St. Louis flights

Top airline flying from Saskatoon to Chicago

Discover the top airline 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 20 June 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 179AverageC$ 520FlexibilityNo cancel feeOn-time60%
Search WestJet 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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