How long is the flight from Saskatchewan to Chicago?

For as low as C$ 501, Air Canada can have you in Chicago from Saskatchewan in 7h 13m. 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 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$ 202+ Cheap Flights from Saskatchewan to Chicago

Cheap flight deals from Saskatchewan to Chicago

Enter your travel dates to find the best prices.

Cheapest

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 17 September 2026.

Sat 21/115:00 a.m. -

1 stop8h 13m

Sat 28/118:40 p.m. -

1 stop14h 03m

Deal found 13/9C$ 453

Wed 14/1011:40 a.m. -

1 stop28h 00m

Fri 16/105:30 p.m. -

1 stop6h 50m

Deal found 16/9C$ 460

Fri 20/115:00 a.m. -

1 stop10h 38m

Sat 28/118:40 p.m. -

1 stop14h 03m

Deal found 15/9C$ 484

Fri 16/103:30 p.m. -

2 stops48h 10m

Mon 19/105:30 p.m. -

1 stop17h 05m

Deal found 13/9C$ 498

Tue 13/101:20 p.m. -

2 stops7h 07m

Tue 20/101:55 p.m. -

2 stops12h 05m

Deal found 15/9C$ 501

Tue 27/109:45 a.m. -

1 stop9h 44m

Tue 3/114:30 p.m. -

1 stop6h 57m

Deal found 12/9C$ 513

Tue 27/1010:50 a.m. -

1 stop9h 37m

Tue 3/115:27 a.m. -

2 stops13h 13m

Deal found 12/9C$ 519

Thu 15/108:55 p.m. -

2 stops16h 40m

Sun 18/103:20 p.m. -

1 stop20h 20m

Deal found 15/9C$ 529

Tue 22/97:55 p.m. -

1 stop16h 28m

Wed 23/93:45 p.m. -

1 stop8h 31m

Deal found 15/9C$ 529

Mon 28/98:35 a.m. -

2 stops11h 58m

Thu 1/108:25 a.m. -

1 stop9h 55m

Deal found 16/9C$ 547

Mon 12/107:00 a.m. -

2 stops16h 59m

Mon 19/105:30 p.m. -

1 stop8h 30m

Deal found 14/9C$ 547

Thu 15/1011:35 a.m. -

1 stop22h 25m

Sun 18/1011:45 a.m. -

1 stop23h 55m

Deal found 15/9C$ 549

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 17 September 2026.

Fri 20/115:00 a.m. -

1 stop10h 38m

Sat 28/118:40 p.m. -

1 stop14h 03m

Deal found 15/9C$ 484

Fri 2/101:20 p.m. -

2 stops7h 13m

Wed 7/1011:19 a.m. -

2 stops12h 51m

Deal found 14/9C$ 501

Sun 1/115:00 a.m. -

1 stop10h 38m

Sun 8/1110:15 a.m. -

1 stop15h 05m

Deal found 17/9C$ 547

Thu 15/1011:35 a.m. -

1 stop22h 25m

Sun 18/1011:45 a.m. -

1 stop23h 55m

Deal found 15/9C$ 549

Sat 10/102:15 p.m. -

1 stop16h 45m

Sat 17/106:00 a.m. -

1 stop16h 30m

Deal found 12/9C$ 559

Mon 12/106:00 a.m. -

2 stops13h 30m

Mon 19/105:30 p.m. -

2 stops23h 00m

Deal found 12/9C$ 764

Tue 13/101:20 p.m. -

2 stops7h 07m

Tue 20/101:55 p.m. -

2 stops12h 05m

Deal found 15/9C$ 501

Fri 16/101:20 p.m. -

2 stops7h 07m

Mon 19/101:25 p.m. -

2 stops12h 35m

Deal found 13/9C$ 501

Fri 20/115:00 a.m. -

1 stop10h 38m

Sun 29/118:40 p.m. -

1 stop14h 03m

Deal found 15/9C$ 580

Tue 22/99:45 a.m. -

1 stop7h 47m

Wed 23/95:55 a.m. -

1 stop16h 35m

Deal found 14/9C$ 587

Mon 12/107:10 a.m. -

2 stops27h 22m

Mon 19/105:30 p.m. -

1 stop8h 30m

Deal found 12/9C$ 628

Tue 27/1010:50 a.m. -

2 stops12h 07m

Tue 3/116:30 a.m. -

2 stops12h 10m

Deal found 12/9C$ 519

Fri 20/1111:50 a.m. -

1 stop9h 43m

Tue 24/1112:38 p.m. -

1 stop6h 02m

Deal found 14/9C$ 519

Mon 12/107:50 p.m. -

1 stop12h 10m

Mon 19/108:40 p.m. -

1 stop14h 06m

Deal found 12/9C$ 635

Mon 5/103:30 p.m. -

3 stops19h 21m

Wed 7/106:30 a.m. -

3 stops19h 30m

Deal found 17/9C$ 637

Fri 30/1010:35 a.m. -

2 stops22h 05m

Fri 6/119:21 p.m. -

1 stop13h 20m

Deal found 15/9C$ 696

Wed 25/116:00 a.m. -

3 stops12h 35m

Sun 29/119:18 a.m. -

3 stops14h 07m

Deal found 14/9C$ 754

Sat 21/115:00 a.m. -

1 stop8h 13m

Sat 21/118:40 p.m. -

1 stop14h 01m

Deal found 15/9C$ 761

Fri 20/1111:35 a.m. -

2 stops22h 04m

Mon 23/118:40 p.m. -

1 stop14h 01m

Deal found 13/9C$ 796

Fri 20/117:00 a.m. -

2 stops11h 04m

Mon 23/119:30 a.m. -

2 stops16h 05m

Deal found 13/9C$ 965

Sun 18/107:00 a.m. -

2 stops8h 47m

Thu 22/106:04 a.m. -

2 stops16h 31m

Deal found 12/9C$ 728

Fri 25/99:05 p.m. -

2 stops16h 30m

Tue 29/93:20 p.m. -

1 stop10h 15m

Deal found 12/9C$ 812

Tue 27/1010:50 a.m. -

2 stops10h 43m

Tue 3/1112:27 p.m. -

2 stops12h 53m

Deal found 12/9C$ 778

Wed 25/1111:15 a.m. -

2 stops23h 10m

Sun 29/119:30 a.m. -

2 stops16h 05m

Deal found 14/9C$ 1,241

Mon 12/106:00 a.m. -

2 stops15h 33m

Mon 19/101:27 p.m. -

2 stops10h 43m

Deal found 12/9C$ 1,243

Wed 14/106:00 a.m. -

2 stops11h 00m

Fri 16/1010:03 a.m. -

1 stop8h 17m

Deal found 16/9C$ 901

Tue 13/107:00 a.m. -

2 stops10h 00m

Sat 21/119:30 a.m. -

2 stops16h 05m

Deal found 14/9C$ 925

Sat 31/1010:50 a.m. -

2 stops10h 43m

Sat 7/119:29 a.m. -

2 stops9h 11m

Deal found 16/9C$ 964

Sat 21/119:30 p.m. -

2 stops12h 54m

Fri 27/115:29 p.m. -

2 stops25h 16m

Deal found 15/9C$ 1,611

Sun 18/106:00 a.m. -

2 stops11h 00m

Thu 22/109:29 a.m. -

2 stops8h 51m

Deal found 15/9C$ 1,046

Find flight deals from Saskatchewan to Chicago

Round-trip from	C$ 453
One-way from	C$ 202

Air Canada
21/11-28/11
2 total stops
22h 16m total
Saskatchewan to Chicago

Search Deals

WestJet
11/10-31/12
1 total stop
6h 50m 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

Thu 22/10

5:40 a.m.-2:55 p.m.

1 stop8h 15m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 252

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 31/10

4:00 a.m.-7:52 p.m.

2 stops14h 52m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 257

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$ 269

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 23/10

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

1 stop8h 40m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 275

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 10/10

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

1 stop18h 35m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 276

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$ 278

SaskatoonChicago

YXE Saskatoon - MDW Chicago Midway

YXEMDW

Saskatoon

Tue 27/10

7:30 a.m.-4:47 p.m.

1 stop8h 17m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 283

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$ 283

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Wed 21/10

5:40 a.m.-1:23 p.m.

1 stop6h 43m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 294

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 10/10

10:45 a.m.-9:27 p.m.

1 stop9h 42m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 298

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/9

Showing 1-10 of 51 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

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

YQR-ORD

YXE-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$ 485). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,052). 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$ 501, Air Canada can have you in Chicago from Saskatchewan in 7h 13m. 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 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$ 485). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,052). 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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Top 2 airlines flying from Saskatchewan to Chicago

Airline	Cheapest	Average	Flexibility	On-time
WestJet	CheapestC$ 177	AverageC$ 491	FlexibilityNo cancel fee	On-time60%	Search WestJet flights
United Airlines	CheapestC$ 430	AverageC$ 600	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.

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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$ 202

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 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 17 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 17 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 17 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 17 September 2026.

Last-minute flights from Saskatchewan to ChicagoDiscover last-minute flight deals from Saskatchewan to Chicago. Data last updated 17 September 2026 and is based on user searches.

Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 17 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 17 September 2026.

Search for one-way flight options from Saskatchewan to Chicago. Find affordable one-way fares based on user searches. Data last updated 17 September 2026.

Find flight deals from Saskatchewan to Chicago

Round-trip from

One-way from

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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 17 September 2026.

Complete your trip

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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 17 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 17 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 17 September 2026.

Last-minute flights from Saskatchewan to Chicago
Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 17 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 17 September 2026.