To save on the cost of your flight from Saskatchewan to Chicago, book at least 38 days before your planned departure. Booking around this time can save you about 198% on the cost of this flight compared to booking a flight leaving this week. We have found prices from C$ 671 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 1,300.
The best pricing can be found in the month of February. Prices to Chicago from Saskatchewan average C$ 693. You can even find prices in February for less than C$ 693, as users have found deals to Chicago from as low as C$ 490. The month of December 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 59%.
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.
Fly from
Fly to
Budget
C$ 418 - C$ 547
Route
Depart
Return
Price
ReginaChicago O'Hare Intl
YQR - ORD
YQRORD
Regina
Sun 16/6
1 stop10h 55m
Chicago O'Hare Intl
Fri 28/6
1 stop19h 03m
SaskatoonChicago O'Hare Intl
YXE - ORD
YXEORD
Saskatoon
Sun 16/6
1 stop11h 40m
Chicago O'Hare Intl
Sun 23/6
1 stop8h 03m
ReginaChicago O'Hare Intl
YQR - ORD
YQRORD
Regina
Sat 22/6
1 stop5h 50m
Chicago O'Hare Intl
Wed 26/6
1 stop9h 23m
ReginaChicago O'Hare Intl
YQR - ORD
YQRORD
Regina
Mon 17/6
1 stop13h 19m
Chicago O'Hare Intl
Mon 24/6
1 stop13h 15m
SaskatoonChicago O'Hare Intl
YXE - ORD
YXEORD
Saskatoon
Wed 10/7
1 stop7h 36m
Chicago O'Hare Intl
Sun 14/7
1 stop18h 58m
ReginaChicago O'Hare Intl
YQR - ORD
YQRORD
Regina
Tue 18/6
2 stops11h 34m
Chicago O'Hare Intl
Wed 26/6
1 stop9h 23m
ReginaChicago Midway
YQR - MDW
YQRMDW
Regina
Tue 18/6
2 stops10h 04m
Chicago Midway
Tue 25/6
1 stop5h 59m
ReginaChicago O'Hare Intl
YQR - ORD
YQRORD
Regina
Mon 17/6
2 stops15h 38m
Chicago O'Hare Intl
Mon 24/6
1 stop13h 15m
SaskatoonChicago O'Hare Intl
YXE - ORD
YXEORD
Saskatoon
Fri 14/6
1 stop28h 22m
Chicago O'Hare Intl
Sat 6/7
1 stop7h 46m
No data available for this route at this time. Please check back soon.
Food
Entertainment
Boarding
Crew
Overall
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Entertainment
Boarding
Crew
Overall
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Entertainment
Boarding
Crew
Overall
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Entertainment
Boarding
Crew
Overall
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
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