Cheap flights from Saskatchewan to Chicago

YXE — CHI
2 Jun — 9 Jun1
Return
1 adult
Economy
From?
To?
Thu 2/6
Thu 9/6

How far in advance should I book a flight from Saskatchewan to Chicago?

To save on the cost of your flight from Saskatchewan to Chicago, book at least 60 days before your planned departure. Booking around this time can save you about 32% on the cost of this flight compared to booking a flight leaving this week. We have found prices from C$ 497 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 663.

What is the cheapest month to fly from Saskatchewan to Chicago?

The best pricing can be found in the month of March. Prices to Chicago from Saskatchewan average C$ 506. You can even find prices in March for less than C$ 506, as users have found deals to Chicago from as low as C$ 373. The month of April appears to be one of the more expensive times to travel to Chicago from Saskatchewan. Flying in the targeted month can save you up to 41%.

When is the cheapest time to fly from Saskatchewan to Chicago (SK - CHI)?

When flying from Saskatchewan to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Saskatchewan to Chicago in May, June 2022

The best prices found for Saskatchewan to CHI flights for May, June
24 Jun. - 4 Jul.
YQR

Regina

ORD

Chicago O'Hare Intl

1 stop

11h 00m
ORD

Chicago O'Hare Intl

YQR

Regina

1 stop

14h 11m
C$ 485

Air Canada

View Deal

Deal found 25.05.22

21 Jun. - 27 Jun.
YQR

Regina

ORD

Chicago O'Hare Intl

2 stops

19h 06m
ORD

Chicago O'Hare Intl

YQR

Regina

1 stop

14h 11m
C$ 488

Multiple Airlines

View Deal

Deal found 27.05.22

21 Jun. - 23 Jun.
YQR

Regina

ORD

Chicago O'Hare Intl

2 stops

19h 06m
ORD

Chicago O'Hare Intl

YQR

Regina

1 stop

6h 39m
C$ 521

WestJet

View Deal

Deal found 27.05.22

Saskatchewan to Chicago 2022 flight deals

Cheap flights to Chicago from Saskatchewan found for this year
7 Oct. - 14 Oct.
YXE

Saskatoon

ORD

Chicago O'Hare Intl

2 stops

18h 51m
ORD

Chicago O'Hare Intl

YXE

Saskatoon

1 stop

7h 01m
C$ 485

WestJet

View Deal

Deal found 26.05.22

24 Jun. - 4 Jul.
YQR

Regina

ORD

Chicago O'Hare Intl

1 stop

11h 00m
ORD

Chicago O'Hare Intl

YQR

Regina

1 stop

14h 11m
C$ 485

Air Canada

View Deal

Deal found 25.05.22

7 Oct. - 14 Oct.
YXE

Saskatoon

ORD

Chicago O'Hare Intl

2 stops

18h 51m
ORD

Chicago O'Hare Intl

YXE

Saskatoon

1 stop

7h 01m
C$ 487

WestJet

View Deal

Deal found 27.05.22

Cheap Air Canada flights from Saskatchewan to Chicago

24 Jun. - 4 Jul.
YQR

Regina

ORD

Chicago O'Hare Intl

1 stop

11h 00m
ORD

Chicago O'Hare Intl

YQR

Regina

1 stop

14h 11m
C$ 485

Air Canada

View Deal

Deal found 25.05.22

20 Jul. - 25 Jul.
YXE

Saskatoon

ORD

Chicago O'Hare Intl

1 stop

13h 05m
ORD

Chicago O'Hare Intl

YXE

Saskatoon

1 stop

14h 23m
C$ 498

Air Canada

View Deal

Deal found 26.05.22

20 Jul. - 25 Jul.
YXE

Saskatoon

ORD

Chicago O'Hare Intl

1 stop

13h 05m
ORD

Chicago O'Hare Intl

YXE

Saskatoon

2 stops

17h 14m
C$ 505

Air Canada

View Deal

Deal found 26.05.22

Cheap WestJet flights from Saskatchewan to Chicago

7 Oct. - 14 Oct.
YXE

Saskatoon

ORD

Chicago O'Hare Intl

2 stops

18h 51m
ORD

Chicago O'Hare Intl

YXE

Saskatoon

1 stop

7h 01m
C$ 485

WestJet

View Deal

Deal found 26.05.22

7 Oct. - 14 Oct.
YXE

Saskatoon

ORD

Chicago O'Hare Intl

2 stops

18h 51m
ORD

Chicago O'Hare Intl

YXE

Saskatoon

1 stop

7h 01m
C$ 487

WestJet

View Deal

Deal found 27.05.22

21 Jun. - 23 Jun.
YQR

Regina

ORD

Chicago O'Hare Intl

2 stops

19h 06m
ORD

Chicago O'Hare Intl

YQR

Regina

1 stop

6h 39m
C$ 521

WestJet

View Deal

Deal found 27.05.22

One-way flights to Chicago All airports from Saskatchewan

The cheapest one-way flights from Saskatchewan to Chicago
21 Sep.
YQR

Regina

ORD

Chicago O'Hare Intl

1 stop

21h 05m
C$ 162

Multiple Airlines

View Deal

Deal found 27.05.22

14 Sep.
YQR

Regina

ORD

Chicago O'Hare Intl

1 stop

20h 45m
C$ 167

Swoop

View Deal

Deal found 27.05.22

8 Jun.
YXE

Saskatoon

ORD

Chicago O'Hare Intl

1 stop

11h 55m
C$ 214

Flair Airlines

View Deal

Deal found 24.05.22

Related info for your journey

Useful info, stats and facts about Saskatchewan to Chicago flights.

Which airlines flying from Saskatchewan to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from Saskatchewan to Chicago have new flexible policies in place due to COVID-19. Air Canada, United Airlines, and WestJet are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like Air Canada with this kind of flexibility.

Can I find flights from Saskatchewan to Chicago for under C$ 500 on Cheapflights?

Yes, there are multiple flights from Saskatchewan to Chicago for under C$ 500. The cheapest flight booked recently is on Air Canada for just C$ 485, but on average you can expect to pay C$ 512.

What are the cheapest airlines to fly from Saskatchewan to Chicago one-way?

The cheapest airlines for a one-way flight from Saskatchewan to Chicago are Swoop (C$ 167), Flair Airlines (C$ 214), and Air Canada (C$ 252).

What are the most popular routes from Saskatchewan to Chicago?

The most popular route from Saskatchewan to Chicago is Saskatoon - Chicago O'Hare Intl. You may also consider Regina - Chicago O'Hare Intl or Saskatoon - Chicago Midway.

What are the most popular airlines that fly from Saskatchewan to Chicago?

Consider Air Canada, United Airlines or WestJet when booking your flight. These represent the most popular airlines when flying from Saskatchewan to Chicago.

Departure points for flights from Saskatchewan to Chicago

Select to see more specific information for flights to Chicago from all departure points in Saskatchewan

Top 3 airlines flying from Saskatchewan to Chicago

The chart below displays the airlines Cheapflights users travelling from Saskatchewan to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Air CanadaCheapestC$ 239AverageC$ 531FlexibilityNo cancel feeOn-time67%COVID-19 safety
Search Air Canada flights
WestJetCheapestC$ 438AverageC$ 760FlexibilityNo cancel feeOn-time60%COVID-19 safety
Search WestJet flights
United AirlinesCheapestC$ 491AverageC$ 653FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights