How long does it take to fly to Chicago?

Flight times from Saskatchewan to Chicago vary, but if you’re flying out of Saskatoon and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 7h 10m on average. Another popular route from Saskatchewan to Chicago is flying from Regina to Chicago O'Hare Intl Airport, which will take roughly 7h 25m. Keep in mind that layovers or delays could extend your travel time.

What is the cheapest airline that flies from Saskatchewan to Chicago?

WestJet, United Airlines, and Air Canada are the most popular carriers operating from Saskatchewan to Chicago

When did momondo last update prices for flights from Saskatchewan to Chicago?

Prices for flights from Saskatchewan to Chicago were last updated today.

How many operators does momondo search for flights from Saskatchewan to Chicago?

There are 2 operators available for flights from Saskatchewan to Chicago as of December 2025.

How old do you have to be to fly from Saskatchewan to Chicago?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Saskatchewan to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

C$ 222 Cheap Flights from Saskatchewan to Chicago in 2025/26

1 adult

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Find the cheapest flights from Saskatchewan to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:10 a.m. - 1:35 p.m.

YQR

ORD

7h 25m1 stop

2:20 p.m. - 9:08 p.m.

ORD

YQR

6h 48m1 stop

C$ 322WestJet

Fri, 23 Jan - Fri, 30 Jan

4:30 p.m. - 1:35 p.m.

YXE

ORD

21h 05m2 stops

2:20 p.m. - 8:58 p.m.

ORD

YXE

6h 38m1 stop

C$ 350WestJet

Thu, 29 Jan - Mon, 2 Feb

9:45 p.m. - 1:35 p.m.

YXE

ORD

15h 50m1 stop

2:20 p.m. - 8:58 p.m.

ORD

YXE

6h 38m1 stop

C$ 352WestJet

Thu, 29 Jan - Mon, 2 Feb

4:30 p.m. - 1:35 p.m.

YXE

ORD

21h 05m2 stops

2:20 p.m. - 8:58 p.m.

ORD

YXE

6h 38m1 stop

C$ 357WestJet

Thu, 29 Jan - Mon, 2 Feb

10:45 a.m. - 11:59 p.m.

YQR

ORD

13h 14m1 stop

7:00 a.m. - 10:51 p.m.

ORD

YQR

15h 51m1 stop

C$ 390United Airlines

Mon, 2 Feb - Tue, 3 Feb

4:25 p.m. - 6:08 p.m.

YQR

ORD

25h 43m2 stops

2:20 p.m. - 10:41 a.m.

ORD

YQR

21h 21m1 stop

C$ 454Multiple Airlines

Mon, 2 Mar - Mon, 9 Mar

7:05 a.m. - 4:52 p.m.

YQR

ORD

33h 47m2 stops

2:20 p.m. - 10:41 a.m.

ORD

YQR

21h 21m1 stop

C$ 457Multiple Airlines

Tue, 3 Mar - Mon, 9 Mar

8:10 a.m. - 5:55 p.m.

YXE

ORD

9h 45m1 stop

3:59 p.m. - 1:48 a.m.

ORD

YXE

9h 49m2 stops

C$ 474Delta

Thu, 29 Jan - Mon, 2 Feb

11:40 a.m. - 9:30 p.m.

YQR

ORD

9h 50m1 stop

12:29 p.m. - 6:31 p.m.

ORD

YQR

6h 02m1 stop

C$ 487Delta

Tue, 3 Mar - Sat, 7 Mar

11:25 a.m. - 7:45 p.m.

YXE

ORD

8h 20m1 stop

6:28 p.m. - 10:35 a.m.

ORD

YXE

16h 07m1 stop

C$ 658Air Canada

Sun, 22 Feb - Thu, 26 Feb

WestJet flights from Saskatchewan to Chicago

Our best WestJet deals on Saskatchewan to Chicago flight tickets

WestJet

23 Jan

YQR6:10 a.m.Regina

7h 25m

1 stop

ORD1:35 p.m.Chicago O'Hare Intl

30 Jan

ORD2:20 p.m.Chicago O'Hare Intl

6h 48m

1 stop

YQR9:08 p.m.Regina

C$ 322

Find similar

WestJet

29 Jan

YXE4:30 p.m.Saskatoon

21h 05m

2 stops

ORD1:35 p.m.Chicago O'Hare Intl

2 Feb

ORD2:20 p.m.Chicago O'Hare Intl

6h 38m

1 stop

YXE8:58 p.m.Saskatoon

C$ 350

Find similar

WestJet

29 Jan

YXE9:45 p.m.Saskatoon

15h 50m

1 stop

ORD1:35 p.m.Chicago O'Hare Intl

2 Feb

ORD2:20 p.m.Chicago O'Hare Intl

6h 38m

1 stop

YXE8:58 p.m.Saskatoon

C$ 352

Find similar

United Airlines flights from Saskatchewan to Chicago

Our best United Airlines deals on Saskatchewan to Chicago flight tickets

United Airlines

2 Feb

YQR10:45 a.m.Regina

13h 14m

1 stop

ORD11:59 p.m.Chicago O'Hare Intl

3 Feb

ORD7:00 a.m.Chicago O'Hare Intl

15h 51m

1 stop

YQR10:51 p.m.Regina

C$ 390

Find similar

United Airlines

1 Feb

YQR10:45 a.m.Regina

8h 01m

1 stop

ORD6:46 p.m.Chicago O'Hare Intl

2 Feb

ORD12:53 p.m.Chicago O'Hare Intl

9h 58m

1 stop

YQR10:51 p.m.Regina

C$ 551

Find similar

United Airlines

2 Feb

YQR10:45 a.m.Regina

13h 14m

1 stop

ORD11:59 p.m.Chicago O'Hare Intl

3 Feb

ORD8:50 a.m.Chicago O'Hare Intl

14h 01m

2 stops

YQR10:51 p.m.Regina

C$ 580

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 23/1

6:10 a.m.-1:35 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Fri 30/1

2:20 p.m.-9:08 p.m.

1 stop6h 48m

C$ 322

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 29/1

4:30 p.m.-1:35 p.m.

2 stops21h 05m

Chicago O'Hare Intl

Mon 2/2

2:20 p.m.-8:58 p.m.

1 stop6h 38m

C$ 350

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 29/1

9:45 p.m.-1:35 p.m.

1 stop15h 50m

Chicago O'Hare Intl

Mon 2/2

2:20 p.m.-8:58 p.m.

1 stop6h 38m

C$ 352

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 29/1

4:30 p.m.-1:35 p.m.

2 stops21h 05m

Chicago O'Hare Intl

Mon 2/2

2:20 p.m.-8:58 p.m.

1 stop6h 38m

C$ 357

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 2/2

10:45 a.m.-11:59 p.m.

1 stop13h 14m

Chicago O'Hare Intl

Tue 3/2

7:00 a.m.-10:51 p.m.

1 stop15h 51m

C$ 390

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 2/3

4:25 p.m.-6:08 p.m.

2 stops25h 43m

Chicago O'Hare Intl

Mon 9/3

2:20 p.m.-10:41 a.m.

1 stop21h 21m

C$ 454

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 3/3

7:05 a.m.-4:52 p.m.

2 stops33h 47m

Chicago O'Hare Intl

Mon 9/3

2:20 p.m.-10:41 a.m.

1 stop21h 21m

C$ 457

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 29/1

8:10 a.m.-5:55 p.m.

1 stop9h 45m

Chicago O'Hare Intl

Mon 2/2

3:59 p.m.-1:48 a.m.

2 stops9h 49m

C$ 474

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 3/3

11:40 a.m.-9:30 p.m.

1 stop9h 50m

Chicago O'Hare Intl

Sat 7/3

12:29 p.m.-6:31 p.m.

1 stop6h 02m

C$ 487

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sun 22/2

11:25 a.m.-7:45 p.m.

1 stop8h 20m

Chicago O'Hare Intl

Thu 26/2

6:28 p.m.-10:35 a.m.

1 stop16h 07m

C$ 658

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Saskatchewan to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of May is another great option to travel to Chicago, with average flight prices from Saskatchewan averaging around C$ 486.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 516. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 697. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the evening is the cheapest time of day to fly from Saskatchewan to Chicago when you can find flight prices for as low as C$ 595. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 686 per ticket.

Can stopping save me money on Saskatchewan to Chicago flights?

You could potentially save up to 16% on your flight if you consider stops on a Saskatchewan to Chicago flight.

Cheap Saskatchewan to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Saskatchewan to Chicago

Fastest flight time	5h 15m
Direct flights	None

The fastest flight from Saskatchewan to Chicago takes 5h 15m

There are no direct flights from Saskatchewan to Chicago. There are no popular flight routes from Saskatchewan to Chicago.

Search flight deals

When did momondo last update prices for flights from Saskatchewan to Chicago?
Prices for flights from Saskatchewan to Chicago were last updated today.
How many operators does momondo search for flights from Saskatchewan to Chicago?
There are 2 operators available for flights from Saskatchewan to Chicago as of December 2025.
How old do you have to be to fly from Saskatchewan to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Saskatchewan to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Saskatchewan to Chicago

Compare and see reviews for airlines that fly from Saskatchewan to Chicago with momondo

Airline	Rating	Free Cancellation	Price
WestJet	PriceFrom C$ 174	Free Cancellation	Rating 7.2 3,214 reviews		Search WestJet flights
Air Canada	PriceFrom C$ 409	Free Cancellation	Rating 7.1 10,551 reviews		Search Air Canada flights

Munster

Hammond

Merrillville

Why use momondo?

Why should I use momondo to find a flight deal from Saskatchewan to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Saskatchewan to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Saskatchewan to Chicago with flexible booking policies on momondo?

Flights from Saskatchewan to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Saskatchewan to Chicago?

Once all potential Saskatchewan to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Saskatchewan to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Saskatchewan and alert you when they change.