How long is the flight from Saskatchewan to Chicago?

For as low as C$ 797, Delta can have you in Chicago from Saskatchewan in 10h 38m. 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 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$ 286+ 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 10 November 2026.

Thu 26/117:30 a.m. -

2 stops13h 25m

Fri 27/1111:00 a.m. -

1 stop7h 40m

Deal found 5/11C$ 590

Mon 23/1111:50 a.m. -

2 stops36h 53m

Fri 27/1111:00 a.m. -

1 stop7h 40m

Deal found 5/11C$ 621

Wed 25/119:10 p.m. -

2 stops16h 34m

Fri 27/1111:00 a.m. -

1 stop7h 40m

Deal found 5/11C$ 648

Thu 26/1111:50 a.m. -

1 stop22h 11m

Tue 1/128:15 a.m. -

2 stops10h 25m

Deal found 5/11C$ 657

Thu 26/1111:50 a.m. -

1 stop22h 11m

Mon 30/118:05 p.m. -

1 stop22h 35m

Deal found 5/11C$ 676

Tue 24/1111:50 a.m. -

1 stop21h 05m

Fri 27/1111:00 a.m. -

1 stop7h 40m

Deal found 5/11C$ 693

Mon 7/125:00 a.m. -

1 stop10h 38m

Mon 7/128:40 p.m. -

1 stop14h 01m

Deal found 9/11C$ 731

Tue 1/128:30 a.m. -

1 stop24h 34m

Sat 5/1212:32 p.m. -

2 stops12h 33m

Deal found 5/11C$ 739

Fri 4/125:00 a.m. -

1 stop10h 38m

Tue 8/124:30 p.m. -

1 stop6h 57m

Deal found 9/11C$ 751

Thu 26/1111:50 a.m. -

1 stop22h 11m

Sat 28/119:55 a.m. -

1 stop8h 45m

Deal found 5/11C$ 755

Mon 23/1111:50 a.m. -

2 stops36h 53m

Mon 30/118:05 p.m. -

1 stop22h 35m

Deal found 5/11C$ 760

Fri 4/124:25 p.m. -

3 stops24h 08m

Tue 8/127:25 a.m. -

3 stops32h 25m

Deal found 9/11C$ 769

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 10 November 2026.

Tue 1/128:30 a.m. -

1 stop24h 34m

Sat 5/1212:32 p.m. -

2 stops12h 33m

Deal found 5/11C$ 739

Tue 5/15:00 a.m. -

1 stop10h 38m

Fri 5/38:50 p.m. -

1 stop13h 46m

Deal found 9/11C$ 797

Mon 23/1110:45 a.m. -

1 stop10h 45m

Fri 27/111:30 p.m. -

1 stop9h 10m

Deal found 6/11C$ 821

Sun 22/118:30 a.m. -

1 stop10h 05m

Mon 23/117:49 a.m. -

2 stops31h 21m

Deal found 5/11C$ 895

Sat 21/119:30 p.m. -

2 stops14h 50m

Mon 23/1112:38 p.m. -

1 stop26h 32m

Deal found 5/11C$ 990

Mon 1/311:50 a.m. -

2 stops12h 09m

Wed 3/39:49 a.m. -

1 stop8h 51m

Deal found 7/11C$ 817

Mon 23/115:00 a.m. -

1 stop8h 13m

Sat 28/114:40 p.m. -

1 stop6h 47m

Deal found 5/11C$ 825

Tue 5/110:45 a.m. -

2 stops21h 07m

Fri 5/39:30 p.m. -

1 stop13h 06m

Deal found 9/11C$ 865

Thu 10/125:35 a.m. -

2 stops9h 18m

Mon 25/112:42 p.m. -

2 stops12h 38m

Deal found 7/11C$ 832

Thu 26/1111:50 a.m. -

1 stop7h 49m

Wed 2/128:04 a.m. -

2 stops10h 36m

Deal found 6/11C$ 876

Sat 21/117:00 a.m. -

1 stop10h 40m

Mon 23/1112:15 p.m. -

1 stop13h 20m

Deal found 5/11C$ 1,089

Fri 20/113:40 p.m. -

1 stop16h 14m

Mon 23/116:17 p.m. -

1 stop16h 24m

Deal found 9/11C$ 1,003

Sat 21/116:00 a.m. -

2 stops8h 55m

Mon 23/1111:19 a.m. -

2 stops14h 16m

Deal found 5/11C$ 981

Fri 20/116:00 a.m. -

2 stops8h 55m

Mon 23/1111:19 a.m. -

2 stops14h 16m

Deal found 9/11C$ 1,093

Find flight deals from Saskatchewan to Chicago

Round-trip from	C$ 590
One-way from	C$ 286

26/11-27/11
3 total stops
21h 05m 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$ 286

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 24/12

8:30 a.m.-10:23 a.m.

1 stop25h 53m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 292

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$ 354

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sat 5/12

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

3 stops19h 04m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 356

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$ 368

Quickest round-trip

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sat 5/12

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$ 377

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Wed 16/12

10:45 a.m.-9:34 p.m.

1 stop10h 49m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 415

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$ 429

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Tue 1/12

8:30 a.m.-9:04 a.m.

1 stop24h 34m

Chicago O'Hare Intl

Sat 5/12

12:32 p.m.-1:05 a.m.

2 stops12h 33m

C$ 739

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 5/1

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

1 stop10h 38m

Chicago O'Hare Intl

Fri 5/3

8:50 p.m.-10:36 a.m.

1 stop13h 46m

C$ 797

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 22 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$ 485). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,064). 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$ 797, Delta can have you in Chicago from Saskatchewan in 10h 38m. 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 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$ 485). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,064). 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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Fort McMurray to O'Hare Intl flights

Victoria to Midway flights

Top 2 airlines flying from Saskatchewan to Chicago

Airline	Cheapest	Average	Flexibility	On-time
WestJet	CheapestC$ 179	AverageC$ 497	FlexibilityNo cancel fee	On-time60%	Search WestJet flights
United Airlines	CheapestC$ 435	AverageC$ 607	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$ 286

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 10 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 10 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 10 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 10 November 2026.

Last-minute flights from Saskatchewan to ChicagoDiscover last-minute flight deals from Saskatchewan to Chicago. Data last updated 10 November 2026 and is based on user searches.

Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 10 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 10 November 2026.

Search for one-way flight options from Saskatchewan to Chicago. Find affordable one-way fares based on user searches. Data last updated 10 November 2026.

Find flight deals from Saskatchewan to Chicago

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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 10 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 10 November 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 10 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 10 November 2026.

Last-minute flights from Saskatchewan to Chicago
Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 10 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 10 November 2026.