Cheap flights from Saskatchewan to Chicago from C$ 244
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 29/7. Fares are subject to change and may not be available on all flights or dates of travel.
Cheap flight deals from Saskatchewan to Chicago
Keep the following information in mind while searching for Saskatchewan to Chicago flight deals. Data was last updated 3 July 2025.
Round-trip from | C$ 350 |
---|---|
One-way from | C$ 244 |
Popular in | February |
Cheapest in | September |
Average price | C$ 601 |
Find flight deals from Saskatchewan to Chicago
Cheapest flights from Saskatchewan to ChicagoExplore the most affordable flight options available from Saskatchewan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3 July 2025.
Explore the most affordable flight options available from Saskatchewan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3 July 2025.
Cheapflights Fare Finder
Customize your flight search to find flights from Saskatchewan to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 3 July 2025.
Use the filters below to find and compare flights from Saskatchewan to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
SaskatoonChicago
YXE - ORD
YXEORD
Saskatoon
Mon 8/9
7:00 a.m.-4:43 p.m.
1 stop8h 43m
Chicago O'Hare Intl
Sat 13/9
5:30 p.m.-12:53 a.m.
1 stop8h 23m
ReginaChicago
YQR - ORD
YQRORD
Regina
Tue 21/10
10:05 a.m.-12:39 p.m.
1 stop25h 34m
Chicago O'Hare Intl
Fri 24/10
5:30 p.m.-1:06 a.m.
1 stop8h 36m
SaskatoonChicago
YXE - ORD
YXEORD
Saskatoon
Fri 1/8
5:20 a.m.-9:30 p.m.
2 stops15h 10m
Chicago O'Hare Intl
Thu 7/8
5:30 p.m.-12:54 a.m.
1 stop8h 24m
ReginaChicago
YQR - ORD
YQRORD
Regina
Fri 15/8
11:25 a.m.-7:29 p.m.
1 stop7h 04m
Chicago O'Hare Intl
Mon 18/8
8:25 p.m.-10:30 a.m.
1 stop15h 05m
SaskatoonChicago
YXE - ORD
YXEORD
Saskatoon
Fri 12/9
6:00 a.m.-6:04 p.m.
2 stops11h 04m
Chicago O'Hare Intl
Sun 14/9
11:08 a.m.-10:43 p.m.
2 stops12h 35m
SaskatoonChicago
YXE - MDW
YXEMDW
Saskatoon
Sat 27/9
5:40 a.m.-6:35 p.m.
2 stops11h 55m
Chicago Midway
Tue 30/9
9:20 a.m.-7:40 p.m.
2 stops11h 20m
SaskatoonChicago
YXE - ORD
YXEORD
Saskatoon
Wed 6/8
6:00 a.m.-3:04 p.m.
1 stop8h 04m
Chicago O'Hare Intl
Sun 10/8
6:20 p.m.-11:59 p.m.
1 stop6h 39m
ReginaChicago
YQR - ORD
YQRORD
Regina
Fri 15/8
11:45 a.m.-4:50 a.m.
3 stops16h 05m
Chicago O'Hare Intl
Mon 18/8
5:30 p.m.-8:05 a.m.
1 stop15h 35m
SaskatoonChicago
YXE - MDW
YXEMDW
Saskatoon
Fri 25/7
5:40 a.m.-4:24 p.m.
1 stop9h 44m
Chicago Midway
Sat 2/8
9:40 a.m.-8:17 a.m.
2 stops23h 37m
SaskatoonChicago
YXE - ORD
YXEORD
Saskatoon
Thu 31/7
5:15 a.m.-12:30 a.m.
2 stops18h 15m
Chicago O'Hare Intl
Thu 7/8
3:50 p.m.-11:56 p.m.
1 stop9h 06m
Best time to book a flight from Saskatchewan to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Saskatchewan with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Saskatchewan to Chicago
What is the cheapest month to book a flight from Saskatchewan to Chicago?
Currently, January is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 261). Flying from Saskatchewan to Chicago in March is currently the most expensive (average of C$ 352). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from SK to CHI?
Find hourly flight availability from Saskatchewan to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 3 July 2025.
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.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 3 July 2025.
Read through reviews of airlines operating flights from Saskatchewan to Chicago, such as Delta,United Airlines, andWestJet. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
Entertainment
Boarding
Food
Overall
Crew
Reviews
Kim,May 2025
PIH - SLC
Comfort
Entertainment
Boarding
Food
Overall
Crew
Reviews
Kim,May 2025
PIH - SLC
Comfort
Entertainment
Boarding
Food
Overall
Crew
Reviews
Kim,May 2025
PIH - SLC
Comfort
Entertainment
Boarding
Food
Overall
Crew
Reviews
Kim,May 2025
PIH - SLC
Comfort
Entertainment
Boarding
Food
Overall
Crew
Reviews
Kim,May 2025
PIH - SLC
Related info for your journey
Find useful and relevant information for your journey from Saskatchewan to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Saskatchewan to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 3 airlines flying from Saskatchewan to Chicago
Discover the top 3 airlines that operate flights from Saskatchewan to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 3 July 2025.
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How does Cheapflights help users find flights from Saskatchewan to Chicago?
When you search for this flight from Saskatchewan to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.
Why should you use Cheapflights to find cheap flight tickets from Saskatchewan to Chicago?
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Saskatchewan.
Can Cheapflights find flights from Saskatchewan to Chicago with no change fees?
Need flexible booking options for your flight to Chicago from Saskatchewan? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.
Can Cheapflights notify me if prices for flights from Saskatchewan to Chicago become cheaper?
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