How long is the flight from Saskatchewan to Chicago?

For as low as C$ 474, Air Canada can have you in Chicago from Saskatchewan in 8h 13m. 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 Regina - Chicago O'Hare Intl. You may also consider Regina - Chicago Midway 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$ 223+ 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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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 27 August 2026.

Wed 28/104:00 a.m. -

1 stop8h 13m

Sat 31/104:30 p.m. -

1 stop6h 57m

Deal found 26/8C$ 474

Mon 28/97:50 p.m. -

1 stop12h 10m

Tue 29/93:45 p.m. -

1 stop8h 31m

Deal found 25/8C$ 506

Mon 26/109:45 a.m. -

1 stop10h 45m

Fri 30/101:00 p.m. -

1 stop9h 40m

Deal found 25/8C$ 510

Thu 8/103:10 p.m. -

2 stops26h 52m

Sun 11/105:30 p.m. -

1 stop6h 40m

Deal found 25/8C$ 517

Tue 1/99:45 a.m. -

1 stop12h 01m

Thu 10/95:55 a.m. -

1 stop16h 35m

Deal found 25/8C$ 519

Fri 11/94:30 p.m. -

2 stops12h 08m

Tue 15/95:30 p.m. -

1 stop6h 40m

Deal found 26/8C$ 544

Tue 22/99:45 a.m. -

1 stop12h 01m

Wed 23/95:55 a.m. -

1 stop16h 35m

Deal found 23/8C$ 549

Mon 26/1011:50 a.m. -

2 stops11h 07m

Fri 30/1012:30 p.m. -

1 stop7h 10m

Deal found 25/8C$ 567

Fri 6/1111:50 a.m. -

2 stops12h 07m

Fri 13/118:04 a.m. -

2 stops10h 36m

Deal found 21/8C$ 570

Wed 9/910:45 a.m. -

1 stop5h 48m

Fri 11/95:30 p.m. -

1 stop6h 50m

Deal found 24/8C$ 578

Tue 22/95:45 a.m. -

2 stops12h 01m

Wed 23/912:59 p.m. -

1 stop7h 06m

Deal found 25/8C$ 617

Fri 6/115:00 a.m. -

1 stop10h 38m

Fri 13/113:56 p.m. -

1 stop6h 44m

Deal found 21/8C$ 653

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 27 August 2026.

Wed 28/104:00 a.m. -

1 stop8h 13m

Sat 31/104:30 p.m. -

1 stop6h 57m

Deal found 26/8C$ 474

Thu 8/103:10 p.m. -

2 stops26h 52m

Sun 11/105:30 p.m. -

1 stop6h 40m

Deal found 25/8C$ 509

Mon 26/109:45 a.m. -

1 stop10h 45m

Fri 30/101:00 p.m. -

1 stop9h 40m

Deal found 25/8C$ 510

Wed 27/16:00 a.m. -

2 stops10h 50m

Fri 5/21:00 p.m. -

2 stops12h 35m

Deal found 22/8C$ 549

Mon 28/97:50 p.m. -

1 stop12h 10m

Tue 29/93:45 p.m. -

1 stop8h 31m

Deal found 25/8C$ 506

Tue 22/99:45 a.m. -

1 stop12h 01m

Wed 23/95:55 a.m. -

1 stop16h 35m

Deal found 25/8C$ 519

Fri 11/94:30 p.m. -

2 stops12h 08m

Tue 15/95:30 p.m. -

1 stop6h 40m

Deal found 26/8C$ 544

Wed 27/16:00 a.m. -

2 stops10h 49m

Fri 5/21:35 p.m. -

2 stops12h 00m

Deal found 22/8C$ 549

Mon 26/107:25 p.m. -

2 stops13h 38m

Fri 30/109:29 a.m. -

2 stops15h 51m

Deal found 25/8C$ 1,155

Thu 28/15:00 a.m. -

2 stops9h 52m

Sat 13/38:50 p.m. -

1 stop12h 46m

Deal found 26/8C$ 537

Mon 26/1011:50 a.m. -

2 stops11h 07m

Fri 30/1012:30 p.m. -

1 stop7h 10m

Deal found 25/8C$ 567

Fri 6/1111:50 a.m. -

2 stops12h 07m

Fri 13/119:59 a.m. -

1 stop8h 41m

Deal found 21/8C$ 570

Wed 9/910:45 a.m. -

2 stops12h 14m

Fri 11/98:25 a.m. -

2 stops11h 00m

Deal found 24/8C$ 578

Sun 27/98:55 p.m. -

1 stop18h 45m

Wed 30/97:28 p.m. -

2 stops27h 07m

Deal found 24/8C$ 761

Thu 28/111:15 a.m. -

2 stops10h 22m

Sun 31/19:30 a.m. -

1 stop5h 40m

Deal found 22/8C$ 596

Sun 27/92:00 p.m. -

3 stops20h 00m

Wed 30/93:20 p.m. -

3 stops22h 25m

Deal found 24/8C$ 881

Thu 28/18:30 a.m. -

1 stop24h 19m

Mon 1/21:00 p.m. -

2 stops12h 35m

Deal found 22/8C$ 747

Tue 22/97:00 a.m. -

2 stops10h 19m

Wed 23/97:13 p.m. -

1 stop27h 22m

Deal found 25/8C$ 761

Fri 6/119:10 p.m. -

2 stops13h 27m

Fri 13/1110:22 a.m. -

1 stop8h 18m

Deal found 21/8C$ 1,392

Thu 8/108:55 p.m. -

3 stops16h 40m

Sun 11/1011:45 a.m. -

3 stops14h 15m

Deal found 25/8C$ 1,102

Mon 28/97:00 a.m. -

2 stops8h 59m

Tue 29/95:30 p.m. -

1 stop6h 40m

Deal found 25/8C$ 763

Fri 11/97:00 a.m. -

2 stops10h 19m

Tue 15/91:00 p.m. -

2 stops9h 35m

Deal found 26/8C$ 933

Tue 26/18:30 a.m. -

1 stop24h 19m

Wed 3/212:30 p.m. -

1 stop26h 40m

Deal found 22/8C$ 933

Sun 18/107:00 a.m. -

2 stops10h 00m

Thu 22/105:31 p.m. -

1 stop24h 49m

Deal found 24/8C$ 955

Thu 28/111:50 a.m. -

2 stops10h 20m

Sat 13/39:55 a.m. -

1 stop8h 45m

Deal found 26/8C$ 965

Find flight deals from Saskatchewan to Chicago

Round-trip from	C$ 474
One-way from	C$ 223

Air Canada
27/10-31/10
2 total stops
15h 10m 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

Quickest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Wed 28/10

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

1 stop8h 13m

Chicago O'Hare Intl

Sat 31/10

4:30 p.m.-10:27 p.m.

1 stop6h 57m

C$ 474

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Mon 28/9

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

1 stop12h 10m

Chicago O'Hare Intl

Tue 29/9

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

1 stop8h 31m

C$ 506

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 8/10

3:10 p.m.-7:02 p.m.

2 stops26h 52m

Chicago O'Hare Intl

Sun 11/10

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

1 stop6h 40m

C$ 509

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Mon 26/10

9:45 a.m.-9:30 p.m.

1 stop10h 45m

Chicago O'Hare Intl

Fri 30/10

1:00 p.m.-9:40 p.m.

1 stop9h 40m

C$ 510

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 22/9

9:45 a.m.-10:46 p.m.

1 stop12h 01m

Chicago O'Hare Intl

Wed 23/9

5:55 a.m.-9:30 p.m.

1 stop16h 35m

C$ 519

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 28/1

5:00 a.m.-2:52 p.m.

2 stops9h 52m

Chicago O'Hare Intl

Sat 13/3

8:50 p.m.-9:36 a.m.

1 stop12h 46m

C$ 537

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 11/9

4:30 p.m.-5:38 a.m.

2 stops12h 08m

Chicago O'Hare Intl

Tue 15/9

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

1 stop6h 40m

C$ 544

SaskatoonChicago

YXE Saskatoon - MDW Chicago Midway

YXEMDW

Saskatoon

Wed 27/1

6:00 a.m.-4:50 p.m.

2 stops10h 50m

Chicago Midway

Fri 5/2

1:00 p.m.-1:35 a.m.

2 stops12h 35m

C$ 549

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Wed 27/1

6:00 a.m.-4:49 p.m.

2 stops10h 49m

Chicago O'Hare Intl

Fri 5/2

1:35 p.m.-1:35 a.m.

2 stops12h 00m

C$ 549

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Mon 26/10

11:50 a.m.-11:57 p.m.

2 stops11h 07m

Chicago O'Hare Intl

Fri 30/10

12:30 p.m.-6:40 p.m.

1 stop7h 10m

C$ 567

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/8

Showing 1-10 of 52 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$ 483). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,046). 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$ 474, Air Canada can have you in Chicago from Saskatchewan in 8h 13m. 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 Regina - Chicago O'Hare Intl. You may also consider Regina - Chicago Midway 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, October is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 483). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,046). 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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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$ 176	AverageC$ 500	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?

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Cheap flights from Saskatchewan to Chicago from C$ 223

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 27 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 27 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 27 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 27 August 2026.

Last-minute flights from Saskatchewan to ChicagoDiscover last-minute flight deals from Saskatchewan to Chicago. Data last updated 27 August 2026 and is based on user searches.

Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 27 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 27 August 2026.

Search for one-way flight options from Saskatchewan to Chicago. Find affordable one-way fares based on user searches. Data last updated 27 August 2026.

Find flight deals from Saskatchewan to Chicago

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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 27 August 2026.

Complete your trip

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Direct flights to Illinois

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Search flights from Saskatchewan to Chicago by cabin class

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Saskatchewan and Chicago flights

Browse other Saskatchewan and Chicago flight options. Last updated on 27 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 27 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 27 August 2026.

Last-minute flights from Saskatchewan to Chicago
Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 27 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 27 August 2026.