How long is the flight from Saskatchewan to Chicago?

For as low as C$ 422, WestJet can have you in Chicago from Saskatchewan in 7h 47m. 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 Saskatoon - 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$ 200+ 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 1 September 2026.

Wed 14/109:05 p.m. -

1 stop18h 35m

Mon 19/105:30 p.m. -

1 stop8h 40m

Deal found 30/8C$ 411

Tue 22/99:45 a.m. -

1 stop7h 47m

Wed 23/95:55 a.m. -

1 stop16h 35m

Deal found 31/8C$ 422

Thu 12/118:30 a.m. -

1 stop10h 05m

Mon 16/1111:42 a.m. -

1 stop27h 28m

Deal found 27/8C$ 454

Mon 28/97:50 p.m. -

1 stop12h 10m

Tue 29/93:45 p.m. -

1 stop8h 31m

Deal found 31/8C$ 458

Fri 23/107:50 p.m. -

1 stop12h 10m

Wed 28/104:30 p.m. -

1 stop8h 01m

Deal found 30/8C$ 462

Tue 15/99:45 a.m. -

1 stop12h 01m

Tue 22/97:00 a.m. -

1 stop15h 30m

Deal found 29/8C$ 470

Tue 6/107:00 a.m. -

1 stop8h 40m

Fri 9/105:30 p.m. -

1 stop6h 50m

Deal found 31/8C$ 491

Tue 6/1010:45 a.m. -

2 stops12h 12m

Fri 9/107:00 a.m. -

2 stops11h 20m

Deal found 31/8C$ 500

Fri 23/107:00 a.m. -

1 stop8h 40m

Wed 28/106:30 a.m. -

2 stops33h 40m

Deal found 30/8C$ 507

Fri 4/1210:45 a.m. -

1 stop10h 49m

Mon 7/128:44 a.m. -

1 stop13h 57m

Deal found 27/8C$ 509

Fri 4/1211:50 a.m. -

2 stops11h 05m

Mon 7/1212:39 p.m. -

1 stop6h 01m

Deal found 27/8C$ 509

Wed 7/106:00 a.m. -

2 stops13h 30m

Fri 9/107:00 a.m. -

2 stops11h 20m

Deal found 31/8C$ 511

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 1 September 2026.

Wed 14/109:05 p.m. -

1 stop18h 35m

Mon 19/105:30 p.m. -

1 stop8h 40m

Deal found 30/8C$ 411

Tue 22/99:45 a.m. -

1 stop7h 47m

Wed 23/95:55 a.m. -

1 stop16h 35m

Deal found 31/8C$ 422

Mon 28/97:50 p.m. -

1 stop12h 10m

Tue 29/93:45 p.m. -

1 stop8h 31m

Deal found 31/8C$ 458

Thu 12/118:30 a.m. -

1 stop10h 05m

Mon 16/118:13 p.m. -

2 stops18h 57m

Deal found 27/8C$ 487

Tue 6/1010:45 a.m. -

2 stops12h 12m

Fri 9/107:00 a.m. -

2 stops11h 20m

Deal found 31/8C$ 500

Fri 23/107:50 p.m. -

1 stop12h 10m

Wed 28/104:30 p.m. -

1 stop8h 01m

Deal found 30/8C$ 462

Tue 15/99:45 a.m. -

1 stop12h 01m

Tue 22/97:00 a.m. -

1 stop15h 30m

Deal found 29/8C$ 470

Fri 4/1211:30 a.m. -

2 stops10h 05m

Mon 7/1212:34 p.m. -

1 stop6h 06m

Deal found 27/8C$ 509

Sat 3/107:00 a.m. -

2 stops12h 30m

Mon 2/113:30 p.m. -

2 stops9h 35m

Deal found 27/8C$ 541

Thu 3/1210:45 a.m. -

1 stop13h 14m

Mon 7/128:44 a.m. -

1 stop13h 57m

Deal found 27/8C$ 509

Fri 4/1211:50 a.m. -

2 stops11h 05m

Mon 7/1212:39 p.m. -

1 stop6h 01m

Deal found 27/8C$ 509

Sat 3/103:30 p.m. -

2 stops24h 03m

Mon 2/1111:45 a.m. -

1 stop27h 25m

Deal found 27/8C$ 601

Fri 4/1210:45 a.m. -

1 stop10h 49m

Mon 7/128:44 a.m. -

1 stop13h 57m

Deal found 27/8C$ 509

Sat 3/106:00 a.m. -

2 stops11h 22m

Mon 2/1112:27 p.m. -

2 stops12h 38m

Deal found 27/8C$ 559

Sat 3/103:30 p.m. -

2 stops24h 03m

Sun 1/117:30 a.m. -

1 stop7h 40m

Deal found 29/8C$ 651

Sat 3/107:50 p.m. -

1 stop12h 10m

Sun 1/118:40 p.m. -

1 stop14h 01m

Deal found 29/8C$ 731

Tue 22/97:00 a.m. -

2 stops10h 19m

Wed 23/97:13 p.m. -

1 stop27h 22m

Deal found 27/8C$ 692

Fri 23/107:00 a.m. -

2 stops12h 30m

Wed 28/106:20 a.m. -

2 stops10h 10m

Deal found 30/8C$ 712

Sun 18/107:00 a.m. -

2 stops10h 00m

Thu 22/109:29 a.m. -

2 stops14h 51m

Deal found 27/8C$ 715

Wed 20/17:00 a.m. -

2 stops29h 33m

Mon 25/15:59 p.m. -

2 stops31h 21m

Deal found 28/8C$ 1,134

Thu 3/125:35 a.m. -

2 stops11h 15m

Mon 7/1212:39 p.m. -

1 stop6h 01m

Deal found 27/8C$ 726

Wed 14/106:00 a.m. -

2 stops11h 00m

Mon 19/1010:12 a.m. -

1 stop8h 08m

Deal found 30/8C$ 727

Tue 10/116:00 a.m. -

2 stops10h 39m

Sat 14/116:44 p.m. -

2 stops30h 51m

Deal found 29/8C$ 1,248

Mon 28/97:00 a.m. -

2 stops8h 59m

Tue 29/95:30 p.m. -

1 stop6h 40m

Deal found 29/8C$ 755

Sat 3/106:00 a.m. -

2 stops11h 22m

Mon 2/1112:27 p.m. -

1 stop26h 43m

Deal found 27/8C$ 1,288

Sat 3/106:00 a.m. -

2 stops11h 22m

Sun 1/1110:01 a.m. -

1 stop5h 09m

Deal found 27/8C$ 779

Thu 12/117:00 a.m. -

2 stops29h 51m

Mon 16/1112:30 p.m. -

2 stops31h 25m

Deal found 29/8C$ 1,386

Fri 23/107:00 a.m. -

2 stops10h 00m

Wed 28/1012:27 p.m. -

2 stops13h 38m

Deal found 30/8C$ 1,114

Find flight deals from Saskatchewan to Chicago

Round-trip from	C$ 411
One-way from	C$ 200

WestJet
14/10-19/10
2 total stops
27h 15m 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

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Wed 14/10

9:05 p.m.-4:40 p.m.

1 stop18h 35m

Chicago O'Hare Intl

Mon 19/10

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

1 stop8h 40m

C$ 411

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 22/9

9:45 a.m.-6:32 p.m.

1 stop7h 47m

Chicago O'Hare Intl

Wed 23/9

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

1 stop16h 35m

C$ 422

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$ 458

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 23/10

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

1 stop12h 10m

Chicago O'Hare Intl

Wed 28/10

4:30 p.m.-11:31 p.m.

1 stop8h 01m

C$ 462

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 15/9

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

1 stop12h 01m

Chicago O'Hare Intl

Tue 22/9

7:00 a.m.-9:30 p.m.

1 stop15h 30m

C$ 470

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 12/11

8:30 a.m.-6:35 p.m.

1 stop10h 05m

Chicago O'Hare Intl

Mon 16/11

8:13 p.m.-3:10 p.m.

2 stops18h 57m

C$ 487

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 6/10

10:45 a.m.-11:57 p.m.

2 stops12h 12m

Chicago O'Hare Intl

Fri 9/10

7:00 a.m.-5:20 p.m.

2 stops11h 20m

C$ 500

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 4/12

11:30 a.m.-9:35 p.m.

2 stops10h 05m

Chicago O'Hare Intl

Mon 7/12

12:34 p.m.-6:40 p.m.

1 stop6h 06m

C$ 509

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 3/12

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

1 stop13h 14m

Chicago O'Hare Intl

Mon 7/12

8:44 a.m.-10:41 p.m.

1 stop13h 57m

C$ 509

ReginaChicago

YQR Regina - MDW Chicago Midway

YQRMDW

Regina

Fri 4/12

11:50 a.m.-10:55 p.m.

2 stops11h 05m

Chicago Midway

Mon 7/12

12:39 p.m.-6:40 p.m.

1 stop6h 01m

C$ 509

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/8

Showing 1-10 of 49 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$ 433). 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$ 422, WestJet can have you in Chicago from Saskatchewan in 7h 47m. 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 Saskatoon - 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$ 433). 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

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Alternative routes for Saskatchewan to Chicago

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Pearson Intl to Moline flights

Grande Prairie to O'Hare Intl flights

Top airline flying from Saskatchewan to Chicago

Airline	Cheapest	Average	Flexibility	On-time
WestJet	CheapestC$ 176	AverageC$ 501	FlexibilityNo cancel fee	On-time60%	Search WestJet flights

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Why should you use Cheapflights to find cheap flight tickets from Saskatchewan to Chicago?

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Can Cheapflights find flights from Saskatchewan to Chicago with no change fees?

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Cheap flights from Saskatchewan to Chicago from C$ 200

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 1 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 1 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 1 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 1 September 2026.

Last-minute flights from Saskatchewan to ChicagoDiscover last-minute flight deals from Saskatchewan to Chicago. Data last updated 1 September 2026 and is based on user searches.

Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 1 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 1 September 2026.

Search for one-way flight options from Saskatchewan to Chicago. Find affordable one-way fares based on user searches. Data last updated 1 September 2026.

Find flight deals from Saskatchewan to Chicago

Round-trip from

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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 1 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 1 September 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 1 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 1 September 2026.

Last-minute flights from Saskatchewan to Chicago
Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 1 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 1 September 2026.