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

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

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 8h 48m on average. Another popular route from Saskatchewan to Chicago is flying from Saskatoon to Chicago O'Hare Intl Airport, which will take roughly 10h 36m. Keep in mind that layovers or delays could extend your travel time.

Which airlines fly to Chicago?

Air Canada, WestJet and Delta are the top three most popular airlines that fly to Chicago from Saskatchewan according to our data. Air Canada is the first choice among our users, with 50% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 3 operators available for flights from Saskatchewan to Chicago as of September 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$ 133 Cheap Flights from Saskatchewan to Chicago in 2025

1 adult

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Find the cheapest flights from Saskatchewan to Chicago

Round-trip

One-way

Cheap round-trip flights

3:45 p.m. - 4:43 p.m.YXE-ORD

23h 58m2 stops

2:20 p.m. - 7:59 p.m.ORD-YXE

6h 39m1 stop

C$ 301WestJet

Find Deal

Fri, 24 Oct - Sun, 26 Oct

8:20 p.m. - 1:35 p.m.YXE-ORD

17h 15m1 stop

2:20 p.m. - 9:46 a.m.ORD-YXE

19h 26m1 stop

C$ 313WestJet

Find Deal

Thu, 29 Jan - Mon, 2 Feb

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

15h 50m1 stop

2:24 p.m. - 2:37 p.m.ORD-YXE

24h 13m1 stop

C$ 330

Find Deal

Thu, 29 Jan - Mon, 2 Feb

11:45 a.m. - 12:15 a.m.YQR-ORD

36h 30m2 stops

2:20 p.m. - 11:45 a.m.ORD-YQR

21h 25m1 stop

C$ 391

Find Deal

Thu, 6 Nov - Fri, 14 Nov

8:10 a.m. - 6:46 p.m.YXE-ORD

10h 36m2 stops

6:00 a.m. - 2:37 p.m.ORD-YXE

8h 37m1 stop

C$ 399Delta

Find Deal

Thu, 29 Jan - Sun, 1 Feb

10:45 a.m. - 7:40 p.m.YQR-ORD

8h 55m1 stop

2:40 p.m. - 10:51 p.m.ORD-YQR

8h 11m1 stop

C$ 470United Airlines

Find Deal

Wed, 5 Nov - Thu, 13 Nov

9:45 a.m. - 11:59 p.m.YQR-ORD

13h 14m1 stop

7:10 a.m. - 9:36 p.m.ORD-YQR

15h 26m1 stop

C$ 477United Airlines

Find Deal

Wed, 8 Oct - Wed, 15 Oct

11:30 a.m. - 7:30 p.m.YXE-ORD

8h 00m1 stop

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

7h 40m1 stop

C$ 580Air Canada

Find Deal

Thu, 29 Jan - Mon, 2 Feb

3:30 p.m. - 11:06 a.m.YXE-ORD

19h 36m2 stops

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

7h 40m1 stop

C$ 621Air Canada

Find Deal

Thu, 29 Jan - Mon, 2 Feb

11:45 a.m. - 5:43 p.m.YQR-MDW

5h 58m1 stop

9:32 a.m. - 6:17 p.m.MDW-YQR

8h 45m2 stops

C$ 711Delta

Find Deal

Thu, 6 Nov - Thu, 13 Nov

United Airlines flights from Saskatchewan to Chicago

Our best United Airlines deals on Saskatchewan to Chicago flight tickets

United Airlines

5 Nov

YQR10:45 a.m.Regina

8h 55m

1 stop

ORD7:40 p.m.Chicago O'Hare Intl

13 Nov

ORD2:40 p.m.Chicago O'Hare Intl

8h 11m

1 stop

YQR10:51 p.m.Regina

C$ 470

Find similar

United Airlines

8 Oct

YQR9:45 a.m.Regina

13h 14m

1 stop

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

15 Oct

ORD7:10 a.m.Chicago O'Hare Intl

15h 26m

1 stop

YQR9:36 p.m.Regina

C$ 477

Find similar

United Airlines

5 Nov

YQR10:45 a.m.Regina

8h 55m

1 stop

ORD7:40 p.m.Chicago O'Hare Intl

6 Nov

ORD2:40 p.m.Chicago O'Hare Intl

8h 11m

1 stop

YQR10:51 p.m.Regina

C$ 490

Find similar

WestJet flights from Saskatchewan to Chicago

Our best WestJet deals on Saskatchewan to Chicago flight tickets

WestJet

24 Oct

YXE3:45 p.m.Saskatoon

23h 58m

2 stops

ORD4:43 p.m.Chicago O'Hare Intl

26 Oct

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

6h 39m

1 stop

YXE7:59 p.m.Saskatoon

C$ 301

Find similar

WestJet

29 Jan

YXE8:20 p.m.Saskatoon

17h 15m

1 stop

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

2 Feb

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

19h 26m

1 stop

YXE9:46 a.m.Saskatoon

C$ 313

Find similar

WestJet

29 Jan

YXE8:20 p.m.Saskatoon

17h 15m

1 stop

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

2 Feb

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

10h 25m

2 stops

YXE12:45 a.m.Saskatoon

C$ 323

Find similar

Fly from

Fly to

Route

Depart

Return

Price

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Fri 24/10

3:45 p.m.-4:43 p.m.

2 stops23h 58m

Chicago O'Hare Intl

Sun 26/10

2:20 p.m.-7:59 p.m.

1 stop6h 39m

C$ 301

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 29/1

8:20 p.m.-1:35 p.m.

1 stop17h 15m

Chicago O'Hare Intl

Mon 2/2

2:20 p.m.-9:46 a.m.

1 stop19h 26m

C$ 313

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

2:24 p.m.-2:37 p.m.

1 stop24h 13m

C$ 330

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 6/11

11:45 a.m.-12:15 a.m.

2 stops36h 30m

Chicago O'Hare Intl

Fri 14/11

2:20 p.m.-11:45 a.m.

1 stop21h 25m

C$ 391

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 29/1

8:10 a.m.-6:46 p.m.

2 stops10h 36m

Chicago O'Hare Intl

Sun 1/2

6:00 a.m.-2:37 p.m.

1 stop8h 37m

C$ 399

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 5/11

10:45 a.m.-7:40 p.m.

1 stop8h 55m

Chicago O'Hare Intl

Thu 13/11

2:40 p.m.-10:51 p.m.

1 stop8h 11m

C$ 470

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 8/10

9:45 a.m.-11:59 p.m.

1 stop13h 14m

Chicago O'Hare Intl

Wed 15/10

7:10 a.m.-9:36 p.m.

1 stop15h 26m

C$ 477

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 29/1

11:30 a.m.-7:30 p.m.

1 stop8h 00m

Chicago O'Hare Intl

Mon 2/2

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

1 stop7h 40m

C$ 580

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Thu 29/1

3:30 p.m.-11:06 a.m.

2 stops19h 36m

Chicago O'Hare Intl

Mon 2/2

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

1 stop7h 40m

C$ 621

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 6/11

11:45 a.m.-5:43 p.m.

1 stop5h 58m

Chicago Midway

Thu 13/11

9:32 a.m.-6:17 p.m.

2 stops8h 45m

C$ 711

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$ 489.

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$ 519. 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$ 701. 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$ 599. 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$ 690 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 3 operators available for flights from Saskatchewan to Chicago as of September 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$ 375	Free Cancellation	Rating 7.2 3,091 reviews	Search WestJet flights
Air Canada	PriceFrom C$ 401	Free Cancellation	Rating 7.1 10,000 reviews	Search Air Canada flights
Delta	PriceFrom C$ 465	Free Cancellation	Rating 7.9 7,960 reviews	Search Delta flights

Munster

Hammond

Merrillville

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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.