How long is the flight from Saskatchewan to Chicago?

For as low as C$ 679, 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 Regina - 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$ 287+ 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 11 November 2026.

Fri 25/1211:50 a.m. -

1 stop6h 55m

Mon 28/127:40 p.m. -

1 stop23h 00m

Deal found 10/11C$ 521

Mon 7/125:00 a.m. -

1 stop10h 38m

Mon 7/128:40 p.m. -

1 stop14h 01m

Deal found 9/11C$ 733

Wed 9/126:50 a.m. -

3 stops22h 11m

Wed 16/1210:00 a.m. -

3 stops29h 30m

Deal found 11/11C$ 748

Wed 9/1212:55 p.m. -

1 stop7h 03m

Wed 16/128:55 p.m. -

1 stop13h 46m

Deal found 11/11C$ 751

Fri 4/125:00 a.m. -

1 stop10h 38m

Tue 8/124:30 p.m. -

1 stop6h 57m

Deal found 9/11C$ 753

Tue 1/128:30 a.m. -

1 stop8h 13m

Sat 5/1212:32 p.m. -

2 stops12h 33m

Deal found 7/11C$ 764

Wed 2/126:00 a.m. -

2 stops15h 35m

Mon 7/128:40 p.m. -

1 stop18h 30m

Deal found 10/11C$ 768

Fri 4/124:25 p.m. -

3 stops24h 08m

Tue 8/127:25 a.m. -

3 stops32h 25m

Deal found 9/11C$ 771

Fri 4/126:45 a.m. -

2 stops14h 51m

Tue 8/1210:36 a.m. -

2 stops29h 14m

Deal found 9/11C$ 773

Thu 10/125:00 a.m. -

1 stop8h 13m

Mon 25/14:30 p.m. -

1 stop6h 57m

Deal found 7/11C$ 778

Wed 2/122:05 p.m. -

3 stops23h 24m

Mon 7/1211:29 a.m. -

3 stops35h 56m

Deal found 10/11C$ 801

Wed 9/126:00 a.m. -

2 stops15h 35m

Wed 16/123:47 p.m. -

1 stop23h 23m

Deal found 11/11C$ 804

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 11 November 2026.

Mon 1/212:55 p.m. -

1 stop7h 03m

Thu 4/210:05 a.m. -

1 stop14h 26m

Deal found 10/11C$ 679

Thu 28/19:30 p.m. -

2 stops21h 17m

Mon 1/29:50 a.m. -

2 stops13h 35m

Deal found 8/11C$ 741

Mon 1/210:15 a.m. -

2 stops11h 21m

Thu 4/26:00 a.m. -

1 stop9h 10m

Deal found 10/11C$ 758

Fri 4/124:25 p.m. -

3 stops24h 08m

Tue 8/127:25 a.m. -

3 stops32h 25m

Deal found 9/11C$ 771

Thu 28/15:00 a.m. -

1 stop8h 13m

Mon 1/28:50 p.m. -

1 stop13h 51m

Deal found 8/11C$ 702

Tue 1/128:30 a.m. -

1 stop6h 23m

Sat 5/125:33 p.m. -

1 stop21h 37m

Deal found 6/11C$ 764

Mon 1/26:50 a.m. -

2 stops15h 02m

Thu 4/29:50 a.m. -

2 stops13h 35m

Deal found 10/11C$ 777

Mon 1/35:00 a.m. -

1 stop8h 13m

Wed 3/38:50 p.m. -

1 stop13h 46m

Deal found 10/11C$ 729

Wed 2/126:00 a.m. -

2 stops15h 35m

Mon 7/128:40 p.m. -

1 stop18h 30m

Deal found 10/11C$ 768

Fri 4/129:10 p.m. -

2 stops15h 14m

Tue 8/126:20 a.m. -

1 stop12h 20m

Deal found 9/11C$ 781

Mon 7/125:00 a.m. -

1 stop10h 38m

Mon 7/128:40 p.m. -

1 stop14h 01m

Deal found 9/11C$ 733

Mon 1/311:50 a.m. -

2 stops12h 09m

Wed 3/39:49 a.m. -

1 stop8h 51m

Deal found 7/11C$ 819

Wed 9/1212:55 p.m. -

1 stop7h 03m

Wed 16/128:55 p.m. -

1 stop13h 46m

Deal found 11/11C$ 751

Thu 10/125:35 a.m. -

2 stops9h 18m

Mon 25/112:42 p.m. -

2 stops12h 38m

Deal found 7/11C$ 835

Thu 26/1111:50 a.m. -

1 stop7h 49m

Wed 2/1212:34 p.m. -

1 stop6h 06m

Deal found 6/11C$ 879

Mon 23/1110:45 a.m. -

1 stop9h 20m

Fri 4/124:07 p.m. -

1 stop6h 50m

Deal found 10/11C$ 911

Find flight deals from Saskatchewan to Chicago

Round-trip from	C$ 521
One-way from	C$ 287

25/12-28/12
2 total stops
29h 55m 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

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Mon 7/12

5:00 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$ 355

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Mon 7/12

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$ 369

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Mon 7/12

6:50 a.m.-9:36 p.m.

2 stops14h 46m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 430

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sat 6/2

5:50 a.m.-12:35 a.m.

3 stops18h 45m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 441

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 25/12

7:00 a.m.-8:44 a.m.

1 stop25h 44m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 458

Quickest round-trip

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sat 26/12

5:00 a.m.-3:38 p.m.

1 stop10h 38m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 471

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 26/12

5:00 a.m.-3:38 p.m.

1 stop10h 38m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 475

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 25/12

3:40 p.m.-8:00 a.m.

2 stops16h 20m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 529

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sat 26/12

2:05 p.m.-1:19 p.m.

3 stops47h 14m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 546

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 28 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

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

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$ 487). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,067). 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$ 679, 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 Regina - 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, September is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 487). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,067). 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

Chicago flight routes

Complete your trip

Direct flights to Illinois

Flights by cabin class

Other flight options

Popular flights

Alternative routes for Saskatchewan to Chicago

Pearson Intl to O'Hare Intl flights

Toronto Island to O'Hare Intl flights

Pierre Elliott Trudeau Intl to O'Hare Intl flights

Pearson Intl to Midway flights

Calgary to O'Hare Intl flights

Pierre Elliott Trudeau Intl to Midway flights

Vancouver Intl to O'Hare Intl flights

Hamilton to O'Hare Intl flights

Toronto Island to Midway flights

Pearson Intl to St. Louis flights

Ottawa to O'Hare Intl flights

Winnipeg to O'Hare Intl flights

Vancouver Intl to Midway flights

Calgary to Midway flights

Québec City to O'Hare Intl flights

Edmonton to O'Hare Intl flights

Edmonton to Midway flights

Pierre Elliott Trudeau Intl to St. Louis flights

Halifax to O'Hare Intl flights

Ottawa to Midway flights

Calgary to St. Louis flights

Kelowna to O'Hare Intl flights

Québec City to Midway flights

Kelowna to Midway flights

Halifax to Midway flights

Saskatoon to O'Hare Intl flights

Vancouver Intl to St. Louis flights

Edmonton to St. Louis flights

St. John's to O'Hare Intl flights

Ottawa to St. Louis flights

London to O'Hare Intl flights

Regina to O'Hare Intl flights

Pearson Intl to Peoria flights

Victoria to O'Hare Intl flights

Region of Waterloo Intl to O'Hare Intl flights

Nanaimo to O'Hare Intl flights

Pearson Intl to Champaign flights

Québec City to St. Louis flights

Moncton to O'Hare Intl flights

Halifax to St. Louis flights

Kingston to O'Hare Intl flights

Victoria to Midway flights

Saskatoon to Midway flights

Pearson Intl to Quincy flights

Saskatoon to St. Louis flights

Top 2 airlines flying from Saskatchewan to Chicago

Airline	Cheapest	Average	Flexibility	On-time
WestJet	CheapestC$ 179	AverageC$ 498	FlexibilityNo cancel fee	On-time60%	Search WestJet flights
United Airlines	CheapestC$ 436	AverageC$ 609	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights

Fly with Cheapflights

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.

Can Cheapflights notify me if prices for flights from Saskatchewan to Chicago become cheaper?

Not ready to book yet? You can track prices for flights from Saskatchewan to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

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 11 November 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 11 November 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 11 November 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 11 November 2026.

Last-minute flights from Saskatchewan to ChicagoDiscover last-minute flight deals from Saskatchewan to Chicago. Data last updated 11 November 2026 and is based on user searches.

Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 11 November 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 11 November 2026.

Search for one-way flight options from Saskatchewan to Chicago. Find affordable one-way fares based on user searches. Data last updated 11 November 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 11 November 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 11 November 2026.

Popular flight searches

Check out other popular destinations found by fellow travellers in 2026

Top 2 airlines flying from Saskatchewan to Chicago

Fly with Cheapflights

How does Cheapflights help users find flights from Saskatchewan to Chicago?

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

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

Can Cheapflights notify me if prices for flights from Saskatchewan to Chicago become cheaper?

100% Free

Book with Flexibility

Travel Smart

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 11 November 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 11 November 2026.

Last-minute flights from Saskatchewan to Chicago
Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 11 November 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 11 November 2026.