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Cheap flights from Saskatoon to Chicago from C$ 289

YXE — CHI
5 Dec — 12 Dec1
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

Tue 1/1211:30 a.m. -
2 stops21h 34m
Sat 5/125:33 p.m. -
1 stop21h 37m
Deal found 4/11C$ 733
Tue 8/128:30 a.m. -
1 stop8h 13m
Wed 9/125:33 p.m. -
1 stop21h 37m
Deal found 2/11C$ 778
Fri 18/126:00 a.m. -
3 stops12h 40m
Fri 25/1211:24 a.m. -
3 stops13h 41m
Deal found 3/11C$ 792
Tue 8/123:40 p.m. -
1 stop16h 14m
Wed 9/129:21 p.m. -
1 stop13h 20m
Deal found 31/10C$ 828
Tue 8/126:50 a.m. -
2 stops14h 46m
Wed 9/1210:36 a.m. -
2 stops12h 49m
Deal found 1/11C$ 857
Tue 1/128:30 a.m. -
1 stop8h 13m
Sat 5/123:47 p.m. -
1 stop23h 23m
Deal found 4/11C$ 869
Fri 18/126:00 a.m. -
2 stops11h 05m
Fri 25/129:59 a.m. -
2 stops22h 11m
Deal found 3/11C$ 976
Fri 18/125:00 a.m. -
1 stop14h 58m
Fri 25/1210:32 a.m. -
2 stops13h 59m
Deal found 3/11C$ 990

Find flight deals from Saskatoon to Chicago

Round-trip from

C$ 700

One-way from

C$ 289
3/1-13/1
  • 3/1-13/1
  • 4 total stops
  • 48h 32m total
  • Saskatoon to Chicago
Search Deals
15/12-31/12
  • 15/12-31/12
  • 2 total stops
  • 13h 30m 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

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Tue 15/12

7:00 a.m.-12:54 a.m.

3 stops17h 54m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 360
Quickest round-trip

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Tue 15/12

8:30 a.m.-2:53 p.m.

1 stop6h 23m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 384

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 17/12

8:30 a.m.-7:45 p.m.

1 stop11h 15m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 406

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sat 19/12

9:30 p.m.-6:55 p.m.

2 stops45h 25m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 424

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Wed 23/12

12:50 p.m.-7:55 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 445

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 18/12

12:50 p.m.-7:55 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 450

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 18/12

8:45 a.m.-5:49 a.m.

3 stops21h 04m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 450

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Tue 22/12

11:30 a.m.-5:49 a.m.

2 stops18h 19m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 450

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sat 19/12

5:00 a.m.-3:38 p.m.

1 stop10h 38m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 571

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sun 3/1

8:30 a.m.-12:13 a.m.

2 stops15h 43m

Chicago O'Hare Intl

Wed 13/1

6:21 a.m.-3:10 p.m.

2 stops32h 49m

C$ 700

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/10

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

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?

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?

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 369.

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: 6h 45m.

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
3,441 reviews
Check prices

Crew

7.9

Comfort

7.1

Boarding

7.4

Entertainment

6.1

Overall

7.2

Food

6.2

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
3,441 reviews
WestJet
7.2
Good
3,441 reviews
Check prices

Crew

7.9

Comfort

7.1

Boarding

7.4

Entertainment

6.1

Overall

7.2

Food

6.2

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
11,860 reviews
WestJet
7.2
Good
3,441 reviews
Check prices

Crew

7.9

Comfort

7.1

Boarding

7.4

Entertainment

6.1

Overall

7.2

Food

6.2

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 Delta fly from Saskatoon to Chicago in about 21h 34m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 1809 km.

  • 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 St. Louis flights
Saskatoon to Midway flights

Top airline flying from Saskatoon to Chicago

AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 177AverageC$ 492FlexibilityNo 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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