How long is the flight from Saskatchewan to Chicago?

For as low as C$ 540, Air Canada can have you in Chicago from Saskatchewan in 5h 17m. The distance from Saskatchewan to Chicago is about 1809 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 Midway. You may also consider Regina - Chicago O'Hare Intl or Saskatoon - Chicago O'Hare Intl.

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$ 261+ 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

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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 22 September 2026.

Wed 14/105:45 a.m. -

1 stop6h 38m

Tue 17/114:30 p.m. -

1 stop6h 57m

Deal found 20/9C$ 464

Fri 20/115:00 a.m. -

1 stop8h 13m

Sat 28/118:40 p.m. -

1 stop14h 03m

Deal found 19/9C$ 498

Sat 21/115:00 a.m. -

1 stop8h 13m

Sat 28/118:40 p.m. -

1 stop14h 03m

Deal found 17/9C$ 502

Fri 30/106:00 a.m. -

1 stop10h 40m

Tue 3/1112:20 p.m. -

1 stop13h 00m

Deal found 18/9C$ 510

Wed 4/115:00 a.m. -

1 stop10h 38m

Wed 11/118:40 p.m. -

1 stop14h 01m

Deal found 20/9C$ 517

Sun 11/103:10 p.m. -

1 stop5h 17m

Thu 15/105:30 p.m. -

1 stop8h 30m

Deal found 17/9C$ 540

Sun 11/103:10 p.m. -

1 stop5h 17m

Fri 16/108:29 a.m. -

2 stops12h 46m

Deal found 17/9C$ 551

Fri 30/1011:50 a.m. -

1 stop8h 37m

Tue 3/115:27 a.m. -

2 stops13h 13m

Deal found 18/9C$ 563

Sat 21/115:35 a.m. -

2 stops11h 06m

Sat 28/119:59 a.m. -

1 stop8h 41m

Deal found 17/9C$ 565

Mon 12/106:00 a.m. -

2 stops17h 24m

Thu 15/105:30 p.m. -

1 stop6h 40m

Deal found 17/9C$ 569

Wed 21/106:00 a.m. -

2 stops13h 30m

Wed 28/1012:30 p.m. -

1 stop7h 10m

Deal found 21/9C$ 576

Fri 20/115:00 a.m. -

1 stop8h 13m

Sun 29/118:40 p.m. -

1 stop14h 03m

Deal found 21/9C$ 591

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 22 September 2026.

Fri 20/115:00 a.m. -

1 stop8h 13m

Sat 28/118:40 p.m. -

1 stop14h 03m

Deal found 19/9C$ 498

Thu 4/210:45 a.m. -

1 stop10h 46m

Mon 8/22:37 p.m. -

1 stop8h 04m

Deal found 19/9C$ 520

Sun 11/103:10 p.m. -

1 stop5h 17m

Thu 15/105:30 p.m. -

1 stop8h 30m

Deal found 17/9C$ 540

Tue 22/128:30 a.m. -

1 stop25h 38m

Sat 30/16:21 a.m. -

2 stops32h 49m

Deal found 18/9C$ 713

Sun 11/103:30 p.m. -

2 stops24h 10m

Thu 15/105:30 p.m. -

2 stops15h 45m

Deal found 17/9C$ 827

Sat 21/115:00 a.m. -

1 stop8h 13m

Sat 28/118:40 p.m. -

1 stop14h 03m

Deal found 19/9C$ 498

Sun 11/103:10 p.m. -

1 stop5h 17m

Fri 16/105:30 p.m. -

1 stop6h 40m

Deal found 17/9C$ 540

Wed 4/115:00 a.m. -

1 stop10h 38m

Wed 11/118:40 p.m. -

1 stop14h 01m

Deal found 20/9C$ 517

Fri 30/1011:50 a.m. -

1 stop8h 37m

Tue 3/115:27 a.m. -

2 stops13h 13m

Deal found 18/9C$ 563

Sat 21/115:35 a.m. -

2 stops11h 06m

Sat 28/119:59 a.m. -

1 stop8h 41m

Deal found 17/9C$ 565

Wed 4/115:00 a.m. -

2 stops26h 44m

Wed 11/116:17 p.m. -

1 stop16h 24m

Deal found 20/9C$ 704

Sun 18/104:30 p.m. -

1 stop23h 10m

Sun 25/104:20 p.m. -

2 stops32h 45m

Deal found 18/9C$ 737

Wed 21/106:00 a.m. -

2 stops13h 30m

Wed 28/1012:30 p.m. -

1 stop7h 10m

Deal found 21/9C$ 576

Thu 17/1212:55 p.m. -

1 stop7h 03m

Sat 2/14:30 p.m. -

1 stop8h 01m

Deal found 21/9C$ 718

Wed 23/125:50 a.m. -

2 stops14h 32m

Mon 4/16:35 p.m. -

1 stop20h 35m

Deal found 18/9C$ 793

Tue 22/1212:55 p.m. -

1 stop7h 03m

Sat 30/18:50 p.m. -

1 stop13h 51m

Deal found 18/9C$ 809

Wed 23/1212:55 p.m. -

1 stop7h 03m

Mon 4/18:50 p.m. -

1 stop13h 51m

Deal found 18/9C$ 810

Find flight deals from Saskatchewan to Chicago

Round-trip from	C$ 464
One-way from	C$ 261

Air Canada
14/10-17/11
2 total stops
13h 35m total
Saskatchewan to Chicago

Search Deals

Air Canada
31/10-31/12
1 total stop
8h 13m 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

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

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$ 261

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sun 11/10

7:50 p.m.-9:00 a.m.

1 stop12h 10m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 265

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$ 269

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$ 282

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sun 11/10

6:00 a.m.-6:29 p.m.

2 stops11h 29m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 292

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 30/10

4:00 a.m.-7:58 p.m.

1 stop14h 58m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 301

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 1/10

7:00 a.m.-4:59 p.m.

2 stops8h 59m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 303

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sun 4/10

5:40 a.m.-7:48 p.m.

1 stop13h 08m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 303

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 5/11

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

2 stops12h 00m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 310

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sun 1/11

8:30 a.m.-5:10 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 311

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/9

Showing 1-10 of 31 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.

YXE-ORD

YQR-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

YXE-ORD

YQR-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$ 482). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,057). 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$ 540, Air Canada can have you in Chicago from Saskatchewan in 5h 17m. The distance from Saskatchewan to Chicago is about 1809 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 Midway. You may also consider Regina - Chicago O'Hare Intl or Saskatoon - Chicago O'Hare Intl.
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$ 482). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,057). 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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Alternative routes for Saskatchewan to Chicago

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Top 2 airlines flying from Saskatchewan to Chicago

Airline	Cheapest	Average	Flexibility	On-time
WestJet	CheapestC$ 177	AverageC$ 494	FlexibilityNo cancel fee	On-time60%	Search WestJet flights
United Airlines	CheapestC$ 432	AverageC$ 603	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights

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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.

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Cheap flights from Saskatchewan to Chicago from C$ 261

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 31/10. 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 22 September 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 22 September 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 22 September 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 22 September 2026.

Last-minute flights from Saskatchewan to ChicagoDiscover last-minute flight deals from Saskatchewan to Chicago. Data last updated 22 September 2026 and is based on user searches.

Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 22 September 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 22 September 2026.

Search for one-way flight options from Saskatchewan to Chicago. Find affordable one-way fares based on user searches. Data last updated 22 September 2026.

Find flight deals from Saskatchewan to Chicago

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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 22 September 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 22 September 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 22 September 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 22 September 2026.

Last-minute flights from Saskatchewan to Chicago
Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 22 September 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 22 September 2026.