How long is the flight from Saskatchewan to Chicago?

For as low as C$ 456, Delta can have you in Chicago from Saskatchewan in 5h 23m. 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 Regina - Chicago O'Hare Intl. You may also consider Saskatoon - Chicago O'Hare Intl or Regina - 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$ 206+ 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 7 September 2026.

Tue 13/107:50 p.m. -

1 stop12h 10m

Fri 27/118:40 p.m. -

1 stop14h 01m

Deal found 5/9C$ 452

Mon 28/97:50 p.m. -

1 stop12h 10m

Tue 29/93:45 p.m. -

1 stop8h 31m

Deal found 2/9C$ 456

Sat 24/1010:45 a.m. -

1 stop9h 42m

Sat 31/109:59 a.m. -

1 stop9h 41m

Deal found 3/9C$ 457

Tue 13/103:10 p.m. -

1 stop5h 17m

Fri 27/1112:38 p.m. -

2 stops12h 27m

Deal found 5/9C$ 475

Tue 29/91:20 p.m. -

2 stops7h 13m

Thu 1/105:30 p.m. -

1 stop6h 40m

Deal found 4/9C$ 477

Sat 3/105:40 a.m. -

1 stop6h 43m

Mon 5/108:40 p.m. -

1 stop13h 20m

Deal found 4/9C$ 489

Sun 4/105:40 a.m. -

1 stop6h 43m

Tue 6/108:40 p.m. -

1 stop13h 20m

Deal found 4/9C$ 500

Tue 22/95:45 a.m. -

1 stop6h 38m

Wed 23/99:55 a.m. -

1 stop10h 10m

Deal found 5/9C$ 507

Sun 4/108:20 p.m. -

2 stops19h 20m

Tue 6/105:30 p.m. -

1 stop8h 40m

Deal found 4/9C$ 517

Tue 3/118:30 a.m. -

1 stop8h 17m

Thu 12/116:00 a.m. -

2 stops9h 10m

Deal found 7/9C$ 529

Wed 21/104:30 p.m. -

1 stop23h 10m

Wed 28/107:15 a.m. -

2 stops32h 55m

Deal found 6/9C$ 556

Sat 3/108:20 p.m. -

2 stops19h 13m

Mon 5/105:30 p.m. -

1 stop6h 50m

Deal found 4/9C$ 560

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 7 September 2026.

Tue 29/93:10 p.m. -

1 stop5h 23m

Fri 2/105:30 p.m. -

1 stop8h 30m

Deal found 3/9C$ 456

Mon 28/97:50 p.m. -

1 stop12h 10m

Tue 29/93:45 p.m. -

1 stop8h 31m

Deal found 6/9C$ 456

Wed 21/1011:25 a.m. -

1 stop28h 15m

Sat 24/1010:00 a.m. -

1 stop14h 10m

Deal found 2/9C$ 603

Sun 4/108:20 p.m. -

2 stops19h 20m

Tue 6/105:30 p.m. -

2 stops18h 45m

Deal found 4/9C$ 763

Sat 24/1010:45 a.m. -

2 stops12h 12m

Sat 31/109:59 a.m. -

1 stop9h 41m

Deal found 3/9C$ 457

Sat 3/105:40 a.m. -

1 stop6h 43m

Mon 5/108:40 p.m. -

1 stop13h 20m

Deal found 4/9C$ 489

Tue 13/103:10 p.m. -

1 stop5h 17m

Fri 27/1112:38 p.m. -

2 stops12h 27m

Deal found 5/9C$ 475

Tue 22/95:45 a.m. -

1 stop6h 38m

Wed 23/99:55 a.m. -

1 stop10h 10m

Deal found 5/9C$ 507

Sat 3/106:00 a.m. -

2 stops13h 30m

Sun 1/116:20 a.m. -

1 stop8h 50m

Deal found 4/9C$ 477

Sat 3/109:05 p.m. -

3 stops18h 28m

Mon 5/105:30 p.m. -

1 stop8h 40m

Deal found 4/9C$ 626

Tue 29/91:20 p.m. -

2 stops7h 13m

Thu 1/101:55 p.m. -

2 stops10h 15m

Deal found 4/9C$ 477

Sat 3/107:50 p.m. -

1 stop12h 10m

Sun 1/118:40 p.m. -

1 stop14h 01m

Deal found 4/9C$ 652

Wed 16/125:00 a.m. -

1 stop8h 13m

Thu 17/128:55 p.m. -

1 stop13h 46m

Deal found 6/9C$ 679

Sat 3/109:05 p.m. -

3 stops16h 30m

Mon 5/103:20 p.m. -

3 stops22h 15m

Deal found 4/9C$ 854

Tue 29/96:00 a.m. -

2 stops11h 33m

Thu 1/1010:48 a.m. -

2 stops14h 47m

Deal found 4/9C$ 945

Mon 28/97:00 a.m. -

2 stops8h 59m

Tue 29/95:30 p.m. -

1 stop6h 40m

Deal found 2/9C$ 699

Sat 19/125:00 a.m. -

1 stop14h 58m

Sat 26/128:50 p.m. -

1 stop13h 53m

Deal found 6/9C$ 724

Fri 16/106:00 a.m. -

2 stops26h 32m

Sun 25/109:29 a.m. -

2 stops40h 06m

Deal found 3/9C$ 1,012

Tue 3/118:30 a.m. -

2 stops14h 03m

Wed 11/1112:30 p.m. -

1 stop26h 40m

Deal found 7/9C$ 715

Sun 8/118:30 a.m. -

1 stop8h 17m

Thu 12/116:00 a.m. -

2 stops9h 10m

Deal found 7/9C$ 788

Sat 3/1010:45 a.m. -

1 stop6h 14m

Mon 5/102:00 p.m. -

2 stops12h 10m

Deal found 4/9C$ 799

Tue 3/118:30 a.m. -

1 stop8h 17m

Mon 9/115:29 p.m. -

1 stop21h 41m

Deal found 7/9C$ 836

Sat 3/106:00 a.m. -

2 stops11h 22m

Sun 1/1110:12 a.m. -

1 stop4h 58m

Deal found 4/9C$ 947

Sun 8/118:30 a.m. -

1 stop8h 17m

Sat 14/115:29 p.m. -

1 stop21h 41m

Deal found 7/9C$ 974

Tue 22/97:00 a.m. -

2 stops10h 19m

Wed 23/97:01 p.m. -

2 stops30h 34m

Deal found 2/9C$ 999

Sun 18/106:00 a.m. -

2 stops11h 00m

Thu 22/1012:27 p.m. -

1 stop5h 53m

Deal found 4/9C$ 1,012

Find flight deals from Saskatchewan to Chicago

Round-trip from	C$ 435
One-way from	C$ 206

United Airlines
22/9-23/9
2 total stops
24h 22m total
Saskatchewan to Chicago

Search Deals

WestJet
11/10-31/12
1 total stop
6h 50m 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

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 25/9

7:50 p.m.-1:23 p.m.

1 stop16h 33m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 245

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$ 252

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

Thu 5/11

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

2 stops12h 00m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 267

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 25/9

11:20 a.m.-1:23 p.m.

2 stops25h 03m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 267

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 30/10

11:50 a.m.-11:57 p.m.

2 stops11h 07m

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

Sat 31/10

10:50 a.m.-9:27 p.m.

1 stop9h 37m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 268

SaskatoonChicago

YXE Saskatoon - MDW Chicago Midway

YXEMDW

Saskatoon

Wed 7/10

6:00 a.m.-6:00 p.m.

2 stops11h 00m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 270

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Wed 7/10

6:00 a.m.-8:30 p.m.

2 stops13h 30m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 270

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 52 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

YQR-MDW

YXE-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

YQR-MDW

YXE-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$ 456, Delta can have you in Chicago from Saskatchewan in 5h 23m. 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 Regina - Chicago O'Hare Intl. You may also consider Saskatoon - Chicago O'Hare Intl or Regina - 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, 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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Alternative routes for Saskatchewan to Chicago

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Nanaimo to O'Hare Intl flights

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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Cheap flights from Saskatchewan to Chicago from C$ 206

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 11/10. 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 7 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 7 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 7 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 7 September 2026.

Last-minute flights from Saskatchewan to ChicagoDiscover last-minute flight deals from Saskatchewan to Chicago. Data last updated 7 September 2026 and is based on user searches.

Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 7 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 7 September 2026.

Search for one-way flight options from Saskatchewan to Chicago. Find affordable one-way fares based on user searches. Data last updated 7 September 2026.

Find flight deals from Saskatchewan to Chicago

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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 7 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

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Saskatchewan and Chicago flights

Browse other Saskatchewan and Chicago flight options. Last updated on 7 September 2026.

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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 7 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 7 September 2026.

Last-minute flights from Saskatchewan to Chicago
Discover last-minute flight deals from Saskatchewan to Chicago. Data last updated 7 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 7 September 2026.