How long is the flight from Saskatchewan to Chicago?

For as low as C$ 571, Air Canada can have you in Chicago from Saskatchewan in 7h 03m. 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 Midway 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$ 287+ 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

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 30 October 2026.

Wed 9/1212:55 p.m. -

1 stop7h 03m

Wed 16/124:30 p.m. -

1 stop8h 01m

Deal found 25/10C$ 571

Sun 13/125:50 a.m. -

2 stops28h 42m

Wed 30/1211:40 a.m. -

1 stop27h 30m

Deal found 27/10C$ 604

Sun 22/118:30 a.m. -

1 stop10h 05m

Tue 24/116:20 p.m. -

2 stops18h 20m

Deal found 26/10C$ 622

Sun 13/125:50 a.m. -

2 stops28h 42m

Mon 28/127:40 p.m. -

1 stop19h 30m

Deal found 27/10C$ 629

Tue 24/115:00 a.m. -

1 stop8h 13m

Sat 28/114:40 p.m. -

1 stop6h 47m

Deal found 26/10C$ 636

Sat 12/125:50 a.m. -

2 stops28h 42m

Wed 30/1211:40 a.m. -

1 stop27h 30m

Deal found 27/10C$ 642

Mon 7/1212:55 p.m. -

1 stop7h 03m

Tue 8/128:40 p.m. -

1 stop14h 01m

Deal found 26/10C$ 643

Thu 10/1211:50 a.m. -

2 stops37h 04m

Thu 17/1211:45 a.m. -

1 stop6h 55m

Deal found 26/10C$ 653

Sat 12/1212:55 p.m. -

1 stop7h 03m

Tue 29/128:50 p.m. -

1 stop13h 51m

Deal found 27/10C$ 659

Sat 5/125:00 a.m. -

1 stop8h 13m

Wed 9/128:45 a.m. -

1 stop15h 46m

Deal found 25/10C$ 660

Sun 22/115:00 a.m. -

1 stop8h 13m

Tue 24/118:40 p.m. -

1 stop14h 01m

Deal found 26/10C$ 663

Thu 10/125:00 a.m. -

1 stop10h 38m

Mon 25/14:30 p.m. -

1 stop6h 57m

Deal found 27/10C$ 670

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 30 October 2026.

Wed 9/1212:55 p.m. -

1 stop7h 03m

Wed 16/124:30 p.m. -

1 stop8h 01m

Deal found 25/10C$ 571

Mon 25/110:45 a.m. -

1 stop8h 05m

Fri 29/14:30 p.m. -

1 stop6h 57m

Deal found 28/10C$ 636

Thu 10/1210:45 a.m. -

2 stops23h 00m

Mon 25/14:30 p.m. -

1 stop6h 57m

Deal found 29/10C$ 733

Sat 5/126:00 a.m. -

2 stops10h 43m

Wed 9/1212:34 p.m. -

1 stop26h 36m

Deal found 27/10C$ 768

Sat 5/1212:55 p.m. -

1 stop7h 03m

Wed 9/124:30 p.m. -

1 stop8h 01m

Deal found 29/10C$ 622

Mon 7/1212:55 p.m. -

1 stop7h 03m

Tue 8/128:40 p.m. -

1 stop14h 01m

Deal found 26/10C$ 643

Mon 25/110:45 a.m. -

1 stop13h 13m

Fri 29/18:21 p.m. -

2 stops26h 36m

Deal found 28/10C$ 744

Mon 4/110:15 a.m. -

2 stops11h 21m

Sat 16/110:33 a.m. -

2 stops15h 02m

Deal found 28/10C$ 800

Thu 10/125:00 a.m. -

1 stop10h 38m

Mon 25/14:30 p.m. -

1 stop6h 57m

Deal found 27/10C$ 670

Sat 12/125:00 a.m. -

1 stop8h 13m

Mon 28/128:50 p.m. -

1 stop13h 51m

Deal found 27/10C$ 764

Mon 4/112:55 p.m. -

1 stop7h 03m

Sat 16/11:55 p.m. -

2 stops10h 36m

Deal found 28/10C$ 846

Wed 18/116:00 a.m. -

2 stops10h 41m

Thu 26/116:00 a.m. -

2 stops9h 10m

Deal found 29/10C$ 814

Thu 10/125:35 a.m. -

2 stops9h 18m

Mon 25/13:36 p.m. -

2 stops9h 44m

Deal found 26/10C$ 820

Thu 18/25:00 a.m. -

1 stop7h 00m

Sun 21/28:50 p.m. -

1 stop13h 53m

Deal found 27/10C$ 983

Tue 24/117:00 a.m. -

2 stops13h 17m

Sat 28/1111:19 a.m. -

2 stops14h 01m

Deal found 26/10C$ 898

Tue 24/115:00 a.m. -

1 stop6h 57m

Tue 24/118:40 p.m. -

1 stop14h 03m

Deal found 26/10C$ 954

Sat 19/1211:50 a.m. -

1 stop9h 49m

Sat 26/1212:33 p.m. -

1 stop6h 07m

Deal found 25/10C$ 927

Find flight deals from Saskatchewan to Chicago

Round-trip from	C$ 571
One-way from	C$ 287

Air Canada
9/12-16/12
2 total stops
15h 04m total
Saskatchewan to Chicago

Search Deals

24/12-31/12
1 total stop
22h 33m 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 24/12

11:50 a.m.-10:23 a.m.

1 stop22h 33m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 287

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 12/12

11:50 a.m.-10:00 p.m.

2 stops10h 10m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 290

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sun 22/11

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

1 stop10h 05m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 298

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Mon 14/12

11:50 a.m.-10:00 p.m.

2 stops34h 10m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 302

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sun 13/12

5:50 a.m.-10:32 a.m.

2 stops28h 42m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 316

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 11/12

5:50 a.m.-12:54 a.m.

3 stops43h 04m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 319

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 10/12

11:50 a.m.-12:54 a.m.

2 stops37h 04m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 327

Quickest round-trip

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 11/12

12:55 p.m.-7:58 p.m.

1 stop7h 03m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 333

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sun 13/12

12:55 p.m.-7:58 p.m.

1 stop7h 03m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 343

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sat 6/2

2:00 p.m.-11:30 a.m.

2 stops21h 30m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 348

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/10

Showing 1-10 of 32 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$ 481). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,055). 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$ 571, Air Canada can have you in Chicago from Saskatchewan in 7h 03m. 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 Midway 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, September is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 481). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,055). 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

Pearson Intl to O'Hare Intl flights

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Pearson Intl to Midway flights

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Region of Waterloo Intl to O'Hare Intl flights

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Pearson Intl to Moline flights

Nanaimo to O'Hare Intl flights

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Victoria to Midway flights

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Victoria to O'Hare Intl flights

Victoria to St. Louis flights

Grande Prairie to O'Hare Intl flights

Saskatoon to St. Louis flights

Vancouver Intl to Peoria flights

Québec City to St. Louis flights

Halifax to St. Louis flights

Top 2 airlines flying from Saskatchewan to Chicago

Airline	Cheapest	Average	Flexibility	On-time
WestJet	CheapestC$ 177	AverageC$ 492	FlexibilityNo cancel fee	On-time60%	Search WestJet flights
United Airlines	CheapestC$ 431	AverageC$ 602	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$ 287

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 24/12. 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 30 October 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 30 October 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 30 October 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 30 October 2026.

Last-minute flights from Saskatchewan to ChicagoDiscover last-minute flight deals from Saskatchewan to Chicago. Data last updated 30 October 2026 and is based on user searches.

Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 30 October 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 30 October 2026.

Search for one-way flight options from Saskatchewan to Chicago. Find affordable one-way fares based on user searches. Data last updated 30 October 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 30 October 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 30 October 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 30 October 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 30 October 2026.

Last-minute flights from Saskatchewan to Chicago
Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 30 October 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 30 October 2026.