How long is the flight from Saskatchewan to Chicago?

For as low as C$ 454, WestJet can have you in Chicago from Saskatchewan in 7h 55m. 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 O'Hare Intl. You may also consider Regina - Chicago O'Hare Intl or Saskatoon - 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$ 216+ 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 21 August 2026.

Mon 12/107:00 a.m. -

1 stop8h 40m

Fri 16/105:30 p.m. -

1 stop6h 40m

Deal found 17/8C$ 394

Fri 28/88:50 a.m. -

1 stop6h 50m

Sun 6/95:30 p.m. -

2 stops15h 45m

Deal found 17/8C$ 396

Thu 10/97:00 a.m. -

1 stop8h 40m

Mon 14/95:30 p.m. -

1 stop6h 40m

Deal found 16/8C$ 430

Fri 2/107:00 a.m. -

1 stop8h 40m

Mon 5/105:30 p.m. -

1 stop6h 50m

Deal found 20/8C$ 433

Thu 10/96:00 a.m. -

1 stop7h 55m

Mon 14/93:45 p.m. -

1 stop8h 31m

Deal found 19/8C$ 454

Thu 17/911:40 a.m. -

1 stop28h 00m

Sun 20/95:30 p.m. -

1 stop8h 40m

Deal found 20/8C$ 472

Mon 14/99:05 p.m. -

1 stop18h 35m

Thu 17/95:30 p.m. -

1 stop6h 50m

Deal found 19/8C$ 478

Fri 28/87:00 a.m. -

1 stop8h 40m

Sun 6/95:30 p.m. -

1 stop8h 30m

Deal found 17/8C$ 498

Thu 10/98:35 a.m. -

1 stop7h 05m

Sun 13/95:30 p.m. -

1 stop8h 40m

Deal found 17/8C$ 507

Thu 17/911:40 a.m. -

1 stop28h 00m

Thu 24/95:30 p.m. -

1 stop6h 50m

Deal found 20/8C$ 523

Thu 10/97:00 a.m. -

1 stop8h 40m

Sun 13/95:30 p.m. -

1 stop8h 40m

Deal found 16/8C$ 564

Fri 18/94:30 p.m. -

2 stops12h 08m

Thu 24/95:30 p.m. -

1 stop6h 40m

Deal found 20/8C$ 568

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 21 August 2026.

Mon 12/107:00 a.m. -

1 stop8h 40m

Fri 16/105:30 p.m. -

1 stop6h 40m

Deal found 17/8C$ 394

Thu 10/96:00 a.m. -

1 stop7h 55m

Mon 14/93:45 p.m. -

1 stop8h 31m

Deal found 19/8C$ 454

Thu 10/97:00 a.m. -

1 stop8h 40m

Sun 13/95:30 p.m. -

1 stop8h 40m

Deal found 16/8C$ 564

Tue 10/1110:45 a.m. -

1 stop13h 14m

Wed 18/111:30 p.m. -

1 stop9h 10m

Deal found 19/8C$ 576

Fri 18/911:35 a.m. -

1 stop7h 45m

Thu 24/95:30 p.m. -

1 stop6h 40m

Deal found 20/8C$ 602

Thu 10/97:00 a.m. -

1 stop8h 40m

Mon 14/95:30 p.m. -

2 stops15h 45m

Deal found 16/8C$ 489

Thu 10/98:35 a.m. -

1 stop7h 05m

Sun 13/95:30 p.m. -

1 stop8h 40m

Deal found 17/8C$ 507

Tue 8/910:45 a.m. -

2 stops12h 14m

Fri 11/95:30 p.m. -

1 stop6h 50m

Deal found 19/8C$ 571

Thu 10/99:45 a.m. -

1 stop13h 14m

Sun 13/95:55 a.m. -

1 stop16h 35m

Deal found 19/8C$ 605

Mon 2/1111:50 a.m. -

2 stops36h 31m

Mon 16/1111:42 a.m. -

1 stop6h 58m

Deal found 20/8C$ 612

Mon 26/1011:55 a.m. -

1 stop7h 18m

Wed 28/109:05 p.m. -

1 stop13h 36m

Deal found 19/8C$ 627

Fri 2/1010:45 a.m. -

2 stops8h 45m

Mon 5/101:55 p.m. -

2 stops10h 25m

Deal found 20/8C$ 572

Thu 17/911:40 a.m. -

1 stop28h 00m

Thu 24/95:30 p.m. -

1 stop6h 50m

Deal found 20/8C$ 523

Mon 14/99:45 a.m. -

1 stop10h 45m

Wed 16/95:55 a.m. -

1 stop16h 35m

Deal found 20/8C$ 605

Fri 2/108:35 a.m. -

1 stop7h 05m

Mon 5/105:30 p.m. -

2 stops18h 45m

Deal found 20/8C$ 523

Mon 14/97:50 p.m. -

1 stop13h 03m

Tue 24/117:03 a.m. -

1 stop7h 43m

Deal found 20/8C$ 681

Wed 9/97:00 a.m. -

2 stops10h 19m

Sat 12/99:59 a.m. -

2 stops16h 01m

Deal found 16/8C$ 623

Mon 14/96:50 p.m. -

2 stops20h 50m

Tue 24/1111:42 a.m. -

3 stops13h 23m

Deal found 20/8C$ 699

Mon 26/106:00 a.m. -

1 stop10h 30m

Wed 28/106:30 a.m. -

2 stops33h 40m

Deal found 19/8C$ 714

Sat 19/1212:55 p.m. -

1 stop7h 03m

Sat 2/14:30 p.m. -

1 stop8h 01m

Deal found 18/8C$ 818

Mon 28/96:00 a.m. -

2 stops11h 01m

Sat 3/102:00 p.m. -

2 stops10h 10m

Deal found 20/8C$ 837

Mon 28/98:55 p.m. -

3 stops16h 40m

Sat 3/1011:45 a.m. -

3 stops14h 15m

Deal found 20/8C$ 917

Fri 2/1010:45 a.m. -

2 stops10h 59m

Mon 5/109:59 a.m. -

1 stop8h 21m

Deal found 20/8C$ 864

Thu 10/910:45 a.m. -

1 stop6h 34m

Sun 13/99:29 a.m. -

2 stops16h 06m

Deal found 16/8C$ 892

Thu 17/99:05 p.m. -

3 stops16h 30m

Sat 19/911:45 a.m. -

3 stops14h 25m

Deal found 17/8C$ 987

Thu 17/97:00 p.m. -

2 stops20h 15m

Sat 19/99:29 a.m. -

2 stops16h 06m

Deal found 17/8C$ 1,062

Mon 28/96:00 a.m. -

2 stops11h 33m

Sat 3/109:29 a.m. -

2 stops16h 06m

Deal found 20/8C$ 1,067

Fri 18/98:55 p.m. -

3 stops16h 40m

Thu 24/911:45 a.m. -

3 stops14h 15m

Deal found 20/8C$ 1,122

Tue 22/97:00 a.m. -

2 stops10h 19m

Wed 23/97:13 p.m. -

1 stop27h 22m

Deal found 17/8C$ 1,084

Sun 20/127:00 a.m. -

2 stops33h 22m

Sat 9/19:30 a.m. -

2 stops40h 05m

Deal found 20/8C$ 1,159

Find flight deals from Saskatchewan to Chicago

Round-trip from	C$ 394
One-way from	C$ 216

WestJet
12/10-16/10
2 total stops
15h 20m total
Saskatchewan to Chicago

Search Deals

WestJet
11/10
1 total stop
8h 40m 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

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Mon 12/10

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Fri 16/10

5:30 p.m.-11:10 p.m.

1 stop6h 40m

C$ 394

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 10/9

6:00 a.m.-2:55 p.m.

1 stop7h 55m

Chicago O'Hare Intl

Mon 14/9

3:45 p.m.-11:16 p.m.

1 stop8h 31m

C$ 454

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 10/9

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Mon 14/9

5:30 p.m.-8:15 a.m.

2 stops15h 45m

C$ 489

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 10/9

8:35 a.m.-4:40 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Sun 13/9

5:30 p.m.-1:10 a.m.

1 stop8h 40m

C$ 507

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 17/9

11:40 a.m.-4:40 p.m.

1 stop28h 00m

Chicago O'Hare Intl

Thu 24/9

5:30 p.m.-11:20 p.m.

1 stop6h 50m

C$ 523

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 2/10

8:35 a.m.-4:40 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Mon 5/10

5:30 p.m.-11:15 a.m.

2 stops18h 45m

C$ 523

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 10/9

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Sun 13/9

5:30 p.m.-1:10 a.m.

1 stop8h 40m

C$ 564

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 8/9

10:45 a.m.-11:59 p.m.

2 stops12h 14m

Chicago O'Hare Intl

Fri 11/9

5:30 p.m.-11:20 p.m.

1 stop6h 50m

C$ 571

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 2/10

10:45 a.m.-8:30 p.m.

2 stops8h 45m

Chicago O'Hare Intl

Mon 5/10

1:55 p.m.-11:20 p.m.

2 stops10h 25m

C$ 572

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 10/11

10:45 a.m.-11:59 p.m.

1 stop13h 14m

Chicago O'Hare Intl

Wed 18/11

1:30 p.m.-10:40 p.m.

1 stop9h 10m

C$ 576

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/8

Showing 1-10 of 60 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

YXE-MDW

YQR-MDW

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

YXE-MDW

YQR-MDW

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

Currently, October is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 403). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,040). 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$ 454, WestJet can have you in Chicago from Saskatchewan in 7h 55m. 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 O'Hare Intl. You may also consider Regina - Chicago O'Hare Intl or Saskatoon - 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, October is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 403). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,040). 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes

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Direct flights to Illinois

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Alternative routes for Saskatchewan to Chicago

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Top airline flying from Saskatchewan to Chicago

Airline	Cheapest	Average	Flexibility	On-time
WestJet	CheapestC$ 175	AverageC$ 498	FlexibilityNo cancel fee	On-time60%	Search WestJet 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$ 216

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 11/10. 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 21 August 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 21 August 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 21 August 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 21 August 2026.

Last-minute flights from Saskatchewan to ChicagoDiscover last-minute flight deals from Saskatchewan to Chicago. Data last updated 21 August 2026 and is based on user searches.

Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 21 August 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 21 August 2026.

Search for one-way flight options from Saskatchewan to Chicago. Find affordable one-way fares based on user searches. Data last updated 21 August 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 21 August 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 21 August 2026.

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Top airline 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 21 August 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 21 August 2026.

Last-minute flights from Saskatchewan to Chicago
Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 21 August 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 21 August 2026.