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Cheap flights from Saskatoon to Chicago from C$ 261

YXE — CHI
21 Oct — 28 Oct1
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

Wed 4/115:00 a.m. -
1 stop10h 38m
Wed 11/118:40 p.m. -
1 stop14h 01m
Deal found 20/9C$ 517
Sun 11/103:10 p.m. -
1 stop5h 17m
Thu 15/101:55 p.m. -
2 stops10h 15m
Deal found 17/9C$ 540
Sun 11/103:10 p.m. -
1 stop5h 17m
Fri 16/108:29 a.m. -
2 stops12h 46m
Deal found 17/9C$ 551
Mon 12/106:00 a.m. -
2 stops17h 24m
Thu 15/105:30 p.m. -
1 stop6h 40m
Deal found 17/9C$ 569
Mon 26/105:50 a.m. -
2 stops22h 26m
Sun 1/117:30 a.m. -
1 stop7h 40m
Deal found 17/9C$ 610
Fri 20/115:00 a.m. -
1 stop8h 13m
Mon 23/118:40 p.m. -
1 stop14h 01m
Deal found 18/9C$ 638
Mon 5/103:30 p.m. -
3 stops19h 21m
Wed 7/106:30 a.m. -
3 stops19h 30m
Deal found 17/9C$ 641
Tue 13/107:50 p.m. -
1 stop12h 10m
Sat 21/118:40 p.m. -
1 stop14h 01m
Deal found 17/9C$ 652
Mon 26/104:00 a.m. -
1 stop10h 38m
Sun 1/118:40 p.m. -
1 stop14h 01m
Deal found 17/9C$ 691
Wed 4/115:00 a.m. -
2 stops26h 44m
Wed 11/116:17 p.m. -
1 stop16h 24m
Deal found 20/9C$ 704
Tue 22/128:30 a.m. -
1 stop25h 38m
Sat 30/16:21 a.m. -
2 stops32h 49m
Deal found 18/9C$ 713
Thu 17/1212:55 p.m. -
1 stop7h 03m
Sat 2/14:30 p.m. -
1 stop8h 01m
Deal found 21/9C$ 718

Find flight deals from Saskatoon to Chicago

Round-trip from

C$ 517

One-way from

C$ 261
Air Canada
  • Air Canada
  • 4/11-11/11
  • 2 total stops
  • 24h 39m total
  • Saskatoon to Chicago
Search Deals
Air Canada
  • Air Canada
  • 31/10-31/12
  • 1 total stop
  • 8h 13m total
  • Saskatoon to Chicago
Search Deals

Cheapflights Fare Finder

 
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
Quickest round-trip

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sat 31/10

4:00 a.m.-1:13 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 261

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 5/11

8:30 a.m.-6:05 p.m.

1 stop9h 35m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 282

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sun 11/10

7:50 p.m.-9:00 a.m.

1 stop12h 10m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 287

SaskatoonChicago

YXE Saskatoon - MDW Chicago Midway

YXEMDW

Saskatoon

Tue 3/11

8:30 a.m.-11:47 p.m.

2 stops15h 17m

Chicago Midway

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 293

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Tue 3/11

8:30 a.m.-12:21 a.m.

2 stops39h 51m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 301

SaskatoonChicago

YXE Saskatoon - MDW Chicago Midway

YXEMDW

Saskatoon

Sun 1/11

8:30 a.m.-4:47 p.m.

1 stop8h 17m

Chicago Midway

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 303

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 1/10

7:00 a.m.-4:59 p.m.

2 stops8h 59m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 303

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 5/11

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

2 stops12h 00m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 310

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sun 11/10

6:00 a.m.-6:29 p.m.

2 stops11h 29m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 313

SaskatoonChicago

YXE Saskatoon - MDW Chicago Midway

YXEMDW

Saskatoon

Sun 1/11

8:30 a.m.-11:22 a.m.

2 stops50h 52m

Chicago Midway

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 392

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/9

Showing 1-10 of 32 resultsSorted by cheapest first
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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

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?

Calgary (YYC) – chosen by Cheapflights users on 50% of one-stop itineraries from Saskatoon to Chicago on Cheapflights.

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

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 374.

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

Flights via Calgary (YYC) have the shortest average one-way travel time for 1-stop routes: 7h 21m.

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

Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 1h 55m.

Reviews of airlines servicing Chicago

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
3,446 reviews
Check prices

Food

6.2

Entertainment

6.1

Comfort

7.1

Crew

7.9

Boarding

7.4

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2026

YHZ - DTW

Better snacks I also flew Delta much better with movies and entertainment
WestJet
7.2
Good
3,446 reviews
WestJet
7.2
Good
3,446 reviews
Check prices

Food

6.2

Entertainment

6.1

Comfort

7.1

Crew

7.9

Boarding

7.4

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2026

YHZ - DTW

Better snacks I also flew Delta much better with movies and entertainment
Air Canada
7.1
Good
11,658 reviews
WestJet
7.2
Good
3,446 reviews
Check prices

Food

6.2

Entertainment

6.1

Comfort

7.1

Crew

7.9

Boarding

7.4

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2026

YHZ - DTW

Better snacks I also flew Delta much better with movies and entertainment

Related info for your journey

  • 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 Air Canada, Delta, and WestJet fly from Saskatoon to Chicago in about 5h 17m. The time it takes to get you to your destination can typically vary by up to 5h 47m. 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$ 177, 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Saskatoon to Chicago

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

Top airline flying from Saskatoon to Chicago

AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 177AverageC$ 494FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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.

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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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