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.
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 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.
Regina
Chicago O'Hare Intl
1 stop
11h 00mChicago O'Hare Intl
Regina
1 stop
14h 11mAir Canada
Regina
Chicago O'Hare Intl
2 stops
19h 06mChicago O'Hare Intl
Regina
1 stop
14h 11mMultiple Airlines
Regina
Chicago O'Hare Intl
2 stops
19h 06mChicago O'Hare Intl
Regina
1 stop
6h 39mWestJet
Saskatoon
Chicago O'Hare Intl
2 stops
18h 51mChicago O'Hare Intl
Saskatoon
1 stop
7h 01mWestJet
Regina
Chicago O'Hare Intl
1 stop
11h 00mChicago O'Hare Intl
Regina
1 stop
14h 11mAir Canada
Saskatoon
Chicago O'Hare Intl
2 stops
18h 51mChicago O'Hare Intl
Saskatoon
1 stop
7h 01mWestJet
Regina
Chicago O'Hare Intl
1 stop
11h 00mChicago O'Hare Intl
Regina
1 stop
14h 11mAir Canada
Saskatoon
Chicago O'Hare Intl
1 stop
13h 05mChicago O'Hare Intl
Saskatoon
1 stop
14h 23mAir Canada
Saskatoon
Chicago O'Hare Intl
1 stop
13h 05mChicago O'Hare Intl
Saskatoon
2 stops
17h 14mAir Canada
Saskatoon
Chicago O'Hare Intl
2 stops
18h 51mChicago O'Hare Intl
Saskatoon
1 stop
7h 01mWestJet
Saskatoon
Chicago O'Hare Intl
2 stops
18h 51mChicago O'Hare Intl
Saskatoon
1 stop
7h 01mWestJet
Regina
Chicago O'Hare Intl
2 stops
19h 06mChicago O'Hare Intl
Regina
1 stop
6h 39mWestJet
Regina
Chicago O'Hare Intl
1 stop
21h 05mMultiple Airlines
Regina
Chicago O'Hare Intl
1 stop
20h 45mSwoop
Saskatoon
Chicago O'Hare Intl
1 stop
11h 55mFlair Airlines
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.
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.
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).
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.
Consider Air Canada, United Airlines or WestJet when booking your flight. These represent the most popular airlines when flying from Saskatchewan to Chicago.