How long is the flight from Saskatchewan to Chicago?

For as low as C$ 502, Air Canada can have you in Chicago from Saskatchewan in 9h 37m. 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 Saskatoon - 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$ 187+ 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 10 September 2026.

Sat 21/115:00 a.m. -

1 stop8h 13m

Sat 28/118:40 p.m. -

1 stop14h 03m

Deal found 10/9C$ 449

Wed 21/107:50 p.m. -

1 stop12h 10m

Wed 28/108:40 p.m. -

1 stop14h 01m

Deal found 6/9C$ 452

Mon 28/97:50 p.m. -

1 stop12h 10m

Tue 29/93:45 p.m. -

1 stop8h 31m

Deal found 6/9C$ 456

Fri 16/108:20 p.m. -

2 stops43h 20m

Mon 19/105:30 p.m. -

1 stop6h 50m

Deal found 10/9C$ 473

Tue 22/95:45 a.m. -

1 stop6h 38m

Wed 23/99:55 a.m. -

1 stop10h 10m

Deal found 7/9C$ 482

Tue 22/94:15 p.m. -

2 stops47h 25m

Tue 29/95:30 p.m. -

1 stop6h 40m

Deal found 9/9C$ 485

Tue 22/99:45 a.m. -

1 stop9h 37m

Wed 23/91:30 p.m. -

1 stop9h 00m

Deal found 9/9C$ 502

Wed 4/115:00 a.m. -

1 stop8h 13m

Mon 9/118:40 p.m. -

1 stop14h 01m

Deal found 7/9C$ 528

Tue 3/118:30 a.m. -

1 stop8h 17m

Thu 12/116:00 a.m. -

2 stops9h 10m

Deal found 7/9C$ 529

Tue 3/118:30 a.m. -

2 stops12h 00m

Sun 15/116:23 a.m. -

1 stop8h 47m

Deal found 7/9C$ 529

Thu 15/107:00 a.m. -

1 stop8h 40m

Sun 18/106:00 a.m. -

2 stops20h 00m

Deal found 7/9C$ 532

Sat 21/115:35 a.m. -

2 stops19h 08m

Sat 28/1110:00 a.m. -

1 stop8h 40m

Deal found 10/9C$ 550

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 September 2026.

Wed 21/107:50 p.m. -

1 stop12h 10m

Wed 28/108:40 p.m. -

1 stop14h 01m

Deal found 6/9C$ 452

Tue 22/94:15 p.m. -

2 stops47h 25m

Tue 29/95:30 p.m. -

1 stop6h 40m

Deal found 9/9C$ 485

Tue 22/99:45 a.m. -

1 stop9h 37m

Wed 23/91:30 p.m. -

1 stop9h 00m

Deal found 9/9C$ 502

Thu 15/107:00 a.m. -

1 stop8h 40m

Sun 18/106:00 a.m. -

2 stops20h 00m

Deal found 7/9C$ 532

Sun 8/1111:15 a.m. -

2 stops10h 12m

Thu 12/116:23 a.m. -

1 stop8h 47m

Deal found 7/9C$ 586

Mon 28/97:50 p.m. -

1 stop12h 10m

Tue 29/93:45 p.m. -

1 stop8h 31m

Deal found 7/9C$ 475

Thu 15/1011:35 a.m. -

1 stop22h 25m

Sun 18/103:20 p.m. -

1 stop20h 20m

Deal found 7/9C$ 1,022

Tue 22/95:45 a.m. -

1 stop6h 38m

Wed 23/99:55 a.m. -

1 stop10h 10m

Deal found 7/9C$ 482

Fri 20/114:25 p.m. -

2 stops18h 05m

Sat 28/1110:00 a.m. -

1 stop8h 40m

Deal found 10/9C$ 579

Mon 9/1111:15 a.m. -

2 stops10h 18m

Thu 12/116:23 a.m. -

1 stop8h 47m

Deal found 7/9C$ 586

Wed 4/1111:15 a.m. -

2 stops10h 12m

Tue 10/115:30 a.m. -

2 stops9h 40m

Deal found 7/9C$ 586

Sat 10/107:50 p.m. -

1 stop15h 10m

Wed 21/108:40 a.m. -

2 stops15h 36m

Deal found 10/9C$ 651

Mon 9/1111:15 a.m. -

2 stops10h 18m

Sun 15/116:23 a.m. -

1 stop8h 47m

Deal found 7/9C$ 586

Sat 2/111:50 a.m. -

1 stop5h 34m

Mon 4/19:55 a.m. -

1 stop8h 45m

Deal found 9/9C$ 586

Sat 2/15:00 a.m. -

1 stop8h 13m

Mon 4/18:50 p.m. -

1 stop13h 53m

Deal found 9/9C$ 676

Thu 15/1011:35 a.m. -

1 stop22h 25m

Sun 18/103:20 p.m. -

2 stops20h 15m

Deal found 7/9C$ 822

Mon 28/97:00 a.m. -

1 stop8h 40m

Tue 29/95:30 p.m. -

1 stop8h 30m

Deal found 9/9C$ 647

Sat 19/125:00 a.m. -

1 stop14h 58m

Sat 26/128:50 p.m. -

1 stop13h 53m

Deal found 6/9C$ 724

Wed 21/101:20 p.m. -

2 stops19h 12m

Wed 28/106:44 p.m. -

2 stops30h 51m

Deal found 6/9C$ 1,104

Tue 3/118:30 a.m. -

1 stop8h 17m

Wed 11/1112:30 p.m. -

1 stop26h 40m

Deal found 7/9C$ 714

Sat 21/1111:25 a.m. -

3 stops23h 16m

Sat 28/1112:55 p.m. -

2 stops29h 45m

Deal found 10/9C$ 1,004

Sat 10/107:00 a.m. -

2 stops10h 00m

Wed 21/101:27 p.m. -

2 stops10h 43m

Deal found 10/9C$ 770

Sun 8/118:30 a.m. -

1 stop8h 17m

Thu 12/116:00 a.m. -

2 stops9h 10m

Deal found 7/9C$ 788

Tue 13/106:00 a.m. -

2 stops11h 00m

Sat 21/119:30 a.m. -

2 stops16h 05m

Deal found 8/9C$ 830

Tue 3/118:30 a.m. -

1 stop8h 17m

Mon 9/115:29 p.m. -

1 stop21h 41m

Deal found 7/9C$ 836

Sun 8/118:30 a.m. -

1 stop8h 17m

Sat 14/115:29 p.m. -

1 stop21h 41m

Deal found 7/9C$ 974

Sun 18/1010:45 a.m. -

1 stop24h 02m

Thu 22/1012:27 p.m. -

1 stop5h 53m

Deal found 7/9C$ 2,490

Sun 18/106:00 a.m. -

2 stops11h 00m

Thu 22/109:29 a.m. -

2 stops8h 51m

Deal found 6/9C$ 1,042

Tue 22/97:00 a.m. -

2 stops10h 19m

Wed 23/97:01 p.m. -

2 stops30h 34m

Deal found 8/9C$ 1,050

Find flight deals from Saskatchewan to Chicago

Round-trip from	C$ 449
One-way from	C$ 187

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

Search Deals

WestJet
24/9-31/12
1 total stop
8h 40m 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

8:50 a.m.-4:40 p.m.

1 stop6h 50m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 206

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 22/9

5:45 a.m.-1:23 p.m.

1 stop6h 38m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 232

Quickest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 10/10

12:40 p.m.-7:48 p.m.

1 stop6h 08m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 240

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Wed 14/10

3:30 p.m.-4:40 p.m.

2 stops24h 10m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 251

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$ 254

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 10/10

11:40 a.m.-4:40 p.m.

1 stop28h 00m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 256

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Sat 24/10

7:50 p.m.-9:23 a.m.

1 stop12h 33m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 267

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 5/11

6:50 a.m.-6:05 p.m.

3 stops11h 15m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 268

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$ 276

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Mon 21/9

10:45 a.m.-9:33 p.m.

1 stop9h 48m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 279

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 59 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

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

YXE-ORD

YQR-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$ 431). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,042). 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$ 502, Air Canada can have you in Chicago from Saskatchewan in 9h 37m. 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 Saskatoon - 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, October is the cheapest month in which you can book a flight from Saskatchewan to Chicago (average of C$ 431). Flying from Saskatchewan to Chicago in February is currently the most expensive (average of C$ 1,042). 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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Complete your trip

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Alternative routes for Saskatchewan to Chicago

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Top airline flying from Saskatchewan to Chicago

Airline	Cheapest	Average	Flexibility	On-time
WestJet	CheapestC$ 175	AverageC$ 499	FlexibilityNo cancel fee	On-time60%	Search WestJet 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?

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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$ 187

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 24/9. 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 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 10 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 10 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 10 September 2026.

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

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

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

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Top airline 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 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 10 September 2026.

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