How long is the flight from Saskatchewan to Chicago?

For as low as C$ 758, Air Canada can have you in Chicago from Saskatchewan in 9h 43m. The distance from Saskatchewan to Chicago is about 1588 km. Both multi-stop and direct flights can be found to your destination and back.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 Saskatoon - Chicago Midway or Regina - Chicago Midway.

What is the cheapest time of day to fly from SK to 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.

Can I find deals for flights from Saskatchewan to Chicago that include hotel bookings?

Yes. In addition to deals on Saskatchewan to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Saskatchewan to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Saskatchewan to Chicago.

Can I find deals for business class flights from Saskatchewan to Chicago?

Yes. Cheapflights offers flight deals from Saskatchewan 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.

C$ 331+ Cheap Flights from Saskatchewan to Chicago

Cheap flight deals from Saskatchewan to Chicago

Enter your travel dates to find the best prices.

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Best

Last-minute

One-way

Cheapest flights from Saskatchewan to Chicago
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 16 October 2026.

Fri 4/1212:55 p.m. -

1 stop7h 03m

Fri 11/124:30 p.m. -

1 stop8h 01m

Deal found 13/10C$ 601

Fri 20/115:00 a.m. -

1 stop10h 38m

Sat 28/114:40 p.m. -

1 stop6h 47m

Deal found 11/10C$ 625

Tue 24/115:00 a.m. -

2 stops10h 02m

Tue 24/118:40 p.m. -

1 stop14h 03m

Deal found 11/10C$ 636

Wed 2/1212:55 p.m. -

1 stop7h 03m

Fri 4/128:40 p.m. -

1 stop14h 01m

Deal found 12/10C$ 659

Thu 29/104:00 a.m. -

1 stop8h 13m

Tue 3/114:30 p.m. -

1 stop8h 01m

Deal found 13/10C$ 667

Tue 22/1211:50 a.m. -

1 stop22h 18m

Tue 5/16:21 a.m. -

2 stops12h 19m

Deal found 11/10C$ 711

Wed 2/124:20 p.m. -

2 stops19h 15m

Fri 4/1212:15 p.m. -

1 stop13h 20m

Deal found 12/10C$ 711

Thu 24/125:00 a.m. -

1 stop10h 38m

Tue 5/14:30 p.m. -

1 stop6h 57m

Deal found 11/10C$ 723

Thu 24/1211:50 a.m. -

1 stop9h 49m

Tue 5/17:00 a.m. -

2 stops11h 40m

Deal found 11/10C$ 754

Tue 10/1111:50 a.m. -

2 stops12h 04m

Tue 17/119:59 a.m. -

1 stop8h 41m

Deal found 13/10C$ 758

Tue 10/1111:50 a.m. -

1 stop9h 43m

Fri 13/115:30 a.m. -

2 stops13h 10m

Deal found 13/10C$ 760

Wed 2/126:00 a.m. -

2 stops10h 43m

Fri 4/126:20 a.m. -

2 stops13h 35m

Deal found 12/10C$ 768

Best flights from Saskatchewan to Chicago
Discover carefully curated flight deals from Saskatchewan to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 16 October 2026.

Fri 20/115:00 a.m. -

1 stop10h 38m

Sat 28/114:40 p.m. -

1 stop6h 47m

Deal found 12/10C$ 625

Wed 2/124:20 p.m. -

2 stops19h 15m

Fri 4/1212:15 p.m. -

1 stop13h 20m

Deal found 12/10C$ 711

Tue 10/1111:50 a.m. -

1 stop9h 43m

Tue 17/119:59 a.m. -

1 stop8h 41m

Deal found 13/10C$ 758

Wed 23/125:55 a.m. -

2 stops27h 39m

Fri 1/110:05 a.m. -

1 stop14h 26m

Deal found 13/10C$ 1,017

Tue 24/115:00 a.m. -

2 stops10h 02m

Tue 24/118:40 p.m. -

1 stop14h 03m

Deal found 11/10C$ 636

Sun 10/15:00 a.m. -

1 stop8h 13m

Sat 20/24:30 p.m. -

1 stop6h 57m

Deal found 10/10C$ 674

Tue 10/1111:50 a.m. -

1 stop9h 43m

Fri 13/115:30 a.m. -

2 stops13h 10m

Deal found 13/10C$ 760

Sun 20/1210:45 a.m. -

1 stop8h 45m

Mon 28/128:50 p.m. -

1 stop13h 53m

Deal found 11/10C$ 836

Wed 2/126:00 a.m. -

2 stops10h 43m

Fri 4/126:20 a.m. -

2 stops13h 35m

Deal found 12/10C$ 768

Sun 20/1210:15 a.m. -

2 stops11h 24m

Sun 3/19:59 a.m. -

1 stop5h 11m

Deal found 13/10C$ 785

Sun 29/113:40 p.m. -

1 stop16h 14m

Sun 6/128:45 a.m. -

1 stop15h 46m

Deal found 15/10C$ 1,044

Sat 19/125:00 a.m. -

1 stop10h 38m

Sat 26/128:50 p.m. -

1 stop13h 53m

Deal found 11/10C$ 870

Sun 29/119:30 p.m. -

2 stops25h 48m

Sun 6/1211:38 a.m. -

1 stop12h 42m

Deal found 15/10C$ 1,015

Wed 11/119:10 p.m. -

3 stops21h 25m

Fri 13/1112:15 p.m. -

1 stop13h 05m

Deal found 13/10C$ 1,038

Sat 19/1211:50 a.m. -

2 stops12h 09m

Mon 28/1212:33 p.m. -

1 stop6h 07m

Deal found 14/10C$ 1,065

Wed 23/1210:15 a.m. -

2 stops11h 24m

Fri 1/16:23 a.m. -

2 stops12h 22m

Deal found 13/10C$ 1,170

Wed 23/1210:15 a.m. -

2 stops11h 24m

Thu 31/126:23 a.m. -

2 stops12h 22m

Deal found 13/10C$ 1,191

Find flight deals from Saskatchewan to Chicago

Round-trip from	C$ 601
One-way from	C$ 331

Air Canada
4/12-11/12
2 total stops
15h 04m total
Saskatchewan to Chicago

Search Deals

12/11-31/12
1 total stop
6h 45m total
Saskatchewan to Chicago

Search Deals

Cheapflights Fare Finder

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

Cheapest round-trip

Quickest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 5/2

5:00 a.m.-1:13 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 331

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 7/1

5:00 a.m.-1:13 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 331

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 12/12

5:00 a.m.-1:13 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 331

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 31/10

4:00 a.m.-1:13 p.m.

1 stop8h 13m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 342

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 5/11

8:30 a.m.-6:05 p.m.

1 stop9h 35m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 368

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 29/10

7:30 a.m.-12:23 p.m.

1 stop27h 53m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 368

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 12/12

11:50 a.m.-12:54 a.m.

2 stops37h 04m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 371

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 5/11

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$ 408

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sat 28/11

7:00 a.m.-7:41 p.m.

1 stop12h 41m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 446

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sun 29/11

3:40 p.m.-7:54 a.m.

1 stop16h 14m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 457

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 28 resultsSorted by cheapest first

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.

YQR-ORD

YXE-ORD

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Saskatchewan to Chicago

CASK-CHI

YQR-ORD

YXE-ORD

What is the cheapest month to book a flight from Saskatchewan to Chicago?

Currently, September is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 488). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,071). 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.

Related info for your journey

How long is the flight from Saskatchewan to Chicago?
For as low as C$ 758, Air Canada can have you in Chicago from Saskatchewan in 9h 43m. The distance from Saskatchewan to Chicago is about 1588 km. Both multi-stop and direct flights can be found to your destination and back.
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 Saskatoon - Chicago Midway or Regina - Chicago Midway.
Can I find deals for flights from Saskatchewan to Chicago that include hotel bookings?
Yes. In addition to deals on Saskatchewan to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Saskatchewan to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Saskatchewan to Chicago.
Can I find deals for business class flights from Saskatchewan to Chicago?
Yes. Cheapflights offers flight deals from Saskatchewan 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.
What is the cheapest month to book a flight from Saskatchewan to Chicago?
Currently, September is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 488). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,071). 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.

See more FAQs

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Complete your trip

Direct flights to Illinois

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Alternative routes for Saskatchewan to Chicago

Pearson Intl to O'Hare Intl flights

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Calgary to Decatur flights

Pearson Intl to Bloomington flights

Top 2 airlines flying from Saskatchewan to Chicago

Airline	Cheapest	Average	Flexibility	On-time
WestJet	CheapestC$ 180	AverageC$ 500	FlexibilityNo cancel fee	On-time60%	Search WestJet flights
United Airlines	CheapestC$ 438	AverageC$ 611	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights

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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.

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Cheap flights from Saskatchewan to Chicago from C$ 331

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/11. Fares are subject to change and may not be available on all flights or dates of travel.

Cheap 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 16 October 2026.

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 16 October 2026.

Best flights from Saskatchewan to ChicagoDiscover carefully curated flight deals from Saskatchewan to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 16 October 2026.

Discover carefully curated flight deals from Saskatchewan to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 16 October 2026.

Last-minute flights from Saskatchewan to ChicagoDiscover last-minute flight deals from Saskatchewan to Chicago. Data last updated 16 October 2026 and is based on user searches.

Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 16 October 2026 and is based on user searches.

One-way flights from Saskatchewan to ChicagoSearch for one-way flight options from Saskatchewan to Chicago. Find affordable one-way fares based on user searches. Data last updated 16 October 2026.

Search for one-way flight options from Saskatchewan to Chicago. Find affordable one-way fares based on user searches. Data last updated 16 October 2026.

Find flight deals from Saskatchewan to Chicago

Round-trip from

One-way from

Cheapflights Fare Finder

Use the filters below to find and compare flights from Saskatchewan to Chicago that are best for you.

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

What is the cheapest month to book a flight from Saskatchewan to Chicago?

Related info for your journey

How long is the flight from Saskatchewan to Chicago?

What are the most popular routes from Saskatchewan to Chicago?

Can I find deals for flights from Saskatchewan to Chicago that include hotel bookings?

How can I find direct flights from Saskatchewan to Chicago?

Can I find deals for business class flights from Saskatchewan to Chicago?

What is the cheapest month to book a flight from Saskatchewan to Chicago?

Browse thousands of different options on Cheapflights for your next trip

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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.

Other flights to Chicago

Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 16 October 2026.

Complete your trip

Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.

Direct flights to Illinois

Book a non-stop flight to one of these other cities located in Illinois.

Search flights from Saskatchewan to Chicago by cabin class

Find flights from Saskatchewan to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Saskatchewan and Chicago flights

Browse other Saskatchewan and Chicago flight options. Last updated on 16 October 2026.

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Top 2 airlines flying from Saskatchewan to Chicago

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Cheapest flights from Saskatchewan to Chicago
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 16 October 2026.

Best flights from Saskatchewan to Chicago
Discover carefully curated flight deals from Saskatchewan to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 16 October 2026.

Last-minute flights from Saskatchewan to Chicago
Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 16 October 2026 and is based on user searches.

One-way flights from Saskatchewan to Chicago
Search for one-way flight options from Saskatchewan to Chicago. Find affordable one-way fares based on user searches. Data last updated 16 October 2026.