How long does it take to fly to Chicago?

Flight times from Saskatchewan to Chicago vary, but if you’re flying out of Regina and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 7h 25m on average. Another popular route from Saskatchewan to Chicago is flying from Saskatoon to Chicago O'Hare Intl Airport, which will take roughly 7h 59m. 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 Delta 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 November 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$ 209 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.

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$ 377WestJet

Find Deal

qui, 29 jan - seg, 2 fev

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$ 378WestJet

Find Deal

qui, 29 jan - seg, 2 fev

3:40 p.m. - 6:48 p.m.YXE-ORD

27h 08m1 stop

7:53 p.m. - 8:55 a.m.ORD-YXE

37h 02m2 stops

C$ 405Multiple Airlines

Find Deal

qui, 29 jan - dom, 8 fev

7:20 p.m. - 3:12 p.m.YQR-ORD

19h 52m2 stops

12:26 p.m. - 6:20 p.m.ORD-YQR

5h 54m1 stop

C$ 450Multiple Airlines

Find Deal

seg, 1 dez - sex, 19 dez

8:10 a.m. - 5:56 p.m.YXE-ORD

9h 46m1 stop

8:50 a.m. - 2:37 p.m.ORD-YXE

5h 47m1 stop

C$ 479Delta

Find Deal

qui, 29 jan - dom, 8 fev

8:10 a.m. - 2:59 p.m.YXE-ORD

6h 49m1 stop

6:35 a.m. - 7:02 p.m.ORD-YXE

12h 27m2 stops

C$ 601Delta

Find Deal

ter, 16 dez - sáb, 20 dez

5:00 a.m. - 1:00 p.m.YXE-ORD

7h 00m1 stop

3:45 p.m. - 11:56 p.m.ORD-YXE

9h 11m1 stop

C$ 618Air Canada

Find Deal

ter, 28 abr - sáb, 2 mai

10:30 a.m. - 7:25 p.m.YXE-ORD

7h 55m1 stop

3:45 p.m. - 11:56 p.m.ORD-YXE

9h 11m1 stop

C$ 620Air Canada

Find Deal

ter, 28 abr - sáb, 2 mai

3:25 p.m. - 8:03 a.m.YXE-ORD

16h 38m1 stop

3:55 p.m. - 11:35 p.m.ORD-YXE

7h 40m1 stop

C$ 710United Airlines

Find Deal

dom, 21 dez - sáb, 10 jan

3:25 p.m. - 8:03 a.m.YXE-ORD

16h 38m1 stop

8:00 a.m. - 2:35 p.m.ORD-YXE

6h 35m1 stop

C$ 713United Airlines

Find Deal

dom, 21 dez - sáb, 10 jan

WestJet flights from Saskatchewan to Chicago

Our best WestJet deals on Saskatchewan to Chicago flight tickets

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$ 377

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$ 378

Find similar

WestJet

29 Jan

YXE10:20 a.m.Saskatoon

27h 15m

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$ 380

Find similar

Air Canada flights from Saskatchewan to Chicago

Our best Air Canada deals on Saskatchewan to Chicago flight tickets

Air Canada

28 Apr

YXE5:00 a.m.Saskatoon

7h 00m

1 stop

ORD1:00 p.m.Chicago O'Hare Intl

2 May

ORD3:45 p.m.Chicago O'Hare Intl

9h 11m

1 stop

YXE11:56 p.m.Saskatoon

C$ 618

Find similar

Air Canada

28 Apr

YXE10:30 a.m.Saskatoon

7h 55m

1 stop

ORD7:25 p.m.Chicago O'Hare Intl

2 May

ORD3:45 p.m.Chicago O'Hare Intl

9h 11m

1 stop

YXE11:56 p.m.Saskatoon

C$ 620

Find similar

Air Canada

28 Apr

YXE10:30 a.m.Saskatoon

7h 55m

1 stop

ORD7:25 p.m.Chicago O'Hare Intl

2 May

ORD3:45 p.m.Chicago O'Hare Intl

9h 11m

1 stop

YXE11:56 p.m.Saskatoon

C$ 621

Find similar

Fly from

Fly to

Route

Depart

Return

Price

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

qui 29/1

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

2 stops21h 05m

Chicago O'Hare Intl

seg 2/2

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

1 stop6h 38m

C$ 377

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

qui 29/1

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

2 stops21h 05m

Chicago O'Hare Intl

seg 2/2

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

1 stop6h 38m

C$ 378

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

qui 29/1

3:40 p.m.-6:48 p.m.

1 stop27h 08m

Chicago O'Hare Intl

dom 8/2

7:53 p.m.-8:55 a.m.

2 stops37h 02m

C$ 405

ReginaChicago

YQR - ORD

YQRORD

Regina

seg 1/12

7:20 p.m.-3:12 p.m.

2 stops19h 52m

Chicago O'Hare Intl

sex 19/12

12:26 p.m.-6:20 p.m.

1 stop5h 54m

C$ 450

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

qui 29/1

8:10 a.m.-5:56 p.m.

1 stop9h 46m

Chicago O'Hare Intl

dom 8/2

8:50 a.m.-2:37 p.m.

1 stop5h 47m

C$ 479

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

ter 16/12

8:10 a.m.-2:59 p.m.

1 stop6h 49m

Chicago O'Hare Intl

sáb 20/12

6:35 a.m.-7:02 p.m.

2 stops12h 27m

C$ 601

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

ter 28/4

5:00 a.m.-1:00 p.m.

1 stop7h 00m

Chicago O'Hare Intl

sáb 2/5

3:45 p.m.-11:56 p.m.

1 stop9h 11m

C$ 618

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

ter 28/4

10:30 a.m.-7:25 p.m.

1 stop7h 55m

Chicago O'Hare Intl

sáb 2/5

3:45 p.m.-11:56 p.m.

1 stop9h 11m

C$ 620

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

dom 21/12

3:25 p.m.-8:03 a.m.

1 stop16h 38m

Chicago O'Hare Intl

sáb 10/1

3:55 p.m.-11:35 p.m.

1 stop7h 40m

C$ 710

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

dom 21/12

3:25 p.m.-8:03 a.m.

1 stop16h 38m

Chicago O'Hare Intl

sáb 10/1

8:00 a.m.-2:35 p.m.

1 stop6h 35m

C$ 713

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 September is another great option to travel to Chicago, with average flight prices from Saskatchewan averaging around C$ 428.

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$ 529. 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$ 714. 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$ 610. 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$ 703 per ticket.

Can stopping save me money on Saskatchewan to Chicago flights?

You could potentially save up to 10% 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

Direct flights	None

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 November 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$ 384	Free Cancellation	Rating 7.2 3,154 reviews		Search WestJet flights
Air Canada	PriceFrom C$ 415	Free Cancellation	Rating 7.1 10,410 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.