How long is the flight from Saskatchewan to Chicago?

For as low as C$ 551, 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 Saskatoon - Chicago Midway. 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$ 265+ 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 2 October 2026.

Mon 14/1210:45 a.m. -

1 stop11h 54m

Fri 8/12:37 p.m. -

1 stop8h 04m

Deal found 28/9C$ 545

Fri 20/115:00 a.m. -

1 stop8h 13m

Sat 28/114:40 p.m. -

1 stop6h 47m

Deal found 27/9C$ 551

Sat 12/125:00 a.m. -

1 stop8h 13m

Mon 11/14:30 p.m. -

1 stop6h 57m

Deal found 27/9C$ 560

Sat 21/115:00 a.m. -

2 stops14h 52m

Sat 28/114:40 p.m. -

1 stop6h 47m

Deal found 28/9C$ 562

Sat 12/125:00 a.m. -

2 stops14h 52m

Tue 5/14:30 p.m. -

1 stop6h 57m

Deal found 27/9C$ 564

Wed 14/109:05 p.m. -

1 stop18h 35m

Fri 16/105:30 p.m. -

1 stop8h 40m

Deal found 28/9C$ 565

Fri 27/115:00 a.m. -

1 stop8h 13m

Mon 30/118:40 p.m. -

1 stop14h 03m

Deal found 28/9C$ 582

Wed 14/105:45 a.m. -

1 stop6h 38m

Sat 31/104:30 p.m. -

1 stop6h 57m

Deal found 28/9C$ 594

Wed 2/125:00 a.m. -

1 stop10h 38m

Fri 4/128:40 p.m. -

1 stop14h 01m

Deal found 30/9C$ 594

Tue 1/125:00 a.m. -

2 stops9h 52m

Wed 16/128:55 p.m. -

1 stop13h 48m

Deal found 1/10C$ 604

Tue 24/115:00 a.m. -

1 stop8h 13m

Tue 24/118:40 p.m. -

1 stop14h 01m

Deal found 29/9C$ 609

Fri 11/125:00 a.m. -

1 stop14h 58m

Wed 6/14:30 p.m. -

1 stop6h 57m

Deal found 27/9C$ 611

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 2 October 2026.

Fri 20/115:00 a.m. -

1 stop8h 13m

Sat 28/114:40 p.m. -

1 stop6h 47m

Deal found 27/9C$ 551

Tue 19/110:45 a.m. -

1 stop8h 10m

Sun 24/14:30 p.m. -

1 stop6h 57m

Deal found 27/9C$ 557

Sat 23/16:00 a.m. -

2 stops10h 49m

Mon 25/13:50 p.m. -

2 stops9h 15m

Deal found 28/9C$ 619

Thu 28/112:55 p.m. -

2 stops18h 55m

Mon 1/28:50 p.m. -

1 stop13h 51m

Deal found 29/9C$ 819

Tue 20/1011:35 a.m. -

1 stop6h 55m

Wed 21/109:46 a.m. -

1 stop25h 54m

Deal found 30/9C$ 860

Wed 2/125:00 a.m. -

1 stop10h 38m

Fri 4/128:40 p.m. -

1 stop14h 01m

Deal found 30/9C$ 594

Wed 27/16:00 a.m. -

2 stops10h 49m

Sun 31/19:30 a.m. -

1 stop5h 40m

Deal found 29/9C$ 629

Tue 1/125:00 a.m. -

2 stops9h 52m

Wed 16/128:55 p.m. -

1 stop13h 48m

Deal found 1/10C$ 604

Sat 12/125:35 a.m. -

2 stops9h 18m

Tue 5/19:50 a.m. -

2 stops8h 50m

Deal found 27/9C$ 644

Mon 2/1110:45 a.m. -

2 stops20h 59m

Fri 6/111:30 p.m. -

1 stop9h 10m

Deal found 29/9C$ 719

Sat 12/125:35 a.m. -

2 stops11h 08m

Mon 11/19:50 a.m. -

2 stops8h 50m

Deal found 27/9C$ 644

Fri 13/1112:55 p.m. -

1 stop7h 03m

Fri 20/118:40 p.m. -

1 stop14h 01m

Deal found 29/9C$ 656

Mon 14/125:35 a.m. -

2 stops11h 08m

Tue 5/19:50 a.m. -

2 stops8h 50m

Deal found 27/9C$ 644

Tue 27/105:30 a.m. -

2 stops16h 16m

Tue 3/1110:30 a.m. -

2 stops14h 01m

Deal found 29/9C$ 863

Mon 8/212:55 p.m. -

1 stop7h 03m

Wed 10/28:50 p.m. -

1 stop13h 51m

Deal found 28/9C$ 696

Tue 24/115:50 a.m. -

3 stops23h 20m

Fri 27/115:01 a.m. -

2 stops20h 34m

Deal found 30/9C$ 849

Wed 16/1211:50 a.m. -

2 stops12h 06m

Sun 10/19:50 a.m. -

2 stops15h 30m

Deal found 27/9C$ 655

Wed 14/1010:45 a.m. -

2 stops12h 12m

Sat 31/109:59 a.m. -

1 stop9h 41m

Deal found 28/9C$ 655

Tue 24/1111:15 a.m. -

2 stops10h 18m

Sun 29/116:23 a.m. -

2 stops12h 22m

Deal found 29/9C$ 666

Tue 27/1010:15 a.m. -

2 stops10h 12m

Tue 3/1112:30 p.m. -

2 stops12h 35m

Deal found 29/9C$ 666

Sat 20/27:00 a.m. -

2 stops13h 37m

Sun 28/21:35 p.m. -

2 stops12h 00m

Deal found 28/9C$ 692

Mon 2/1111:50 a.m. -

2 stops12h 07m

Fri 6/118:29 a.m. -

2 stops16h 51m

Deal found 29/9C$ 716

Find flight deals from Saskatchewan to Chicago

Round-trip from	C$ 545
One-way from	C$ 265

United Airlines
14/12-8/1
2 total stops
19h 58m total
Saskatchewan to Chicago

Search Deals

Air Canada
12/11-31/12
1 total stop
7h 03m 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

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sun 11/10

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

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 12/11

6:50 a.m.-6:35 p.m.

3 stops11h 45m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 310

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Mon 23/11

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

2 stops10h 00m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 322

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$ 323

Quickest round-trip

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$ 325

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 13/11

11:50 a.m.-12:21 a.m.

2 stops36h 31m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 326

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 5/11

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$ 326

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 12/11

7:00 a.m.-8:17 p.m.

2 stops13h 17m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 349

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 30/10

4:00 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$ 349

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Wed 11/11

11:50 a.m.-9:33 p.m.

1 stop9h 43m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 362

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/9

Showing 1-10 of 37 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$ 490). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,074). 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$ 551, 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 Saskatoon - Chicago Midway. 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$ 490). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,074). 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

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Top 2 airlines flying from Saskatchewan to Chicago

Airline	Cheapest	Average	Flexibility	On-time
WestJet	CheapestC$ 180	AverageC$ 501	FlexibilityNo cancel fee	On-time60%	Search WestJet flights
United Airlines	CheapestC$ 439	AverageC$ 613	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$ 265

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 12/11. 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 2 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 2 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 2 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 2 October 2026.

Last-minute flights from Saskatchewan to ChicagoDiscover last-minute flight deals from Saskatchewan to Chicago. Data last updated 2 October 2026 and is based on user searches.

Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 2 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 2 October 2026.

Search for one-way flight options from Saskatchewan to Chicago. Find affordable one-way fares based on user searches. Data last updated 2 October 2026.

Find flight deals from Saskatchewan to Chicago

Round-trip 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 2 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 2 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 2 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 2 October 2026.

Last-minute flights from Saskatchewan to Chicago
Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 2 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 2 October 2026.