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

Air Canada, Porter Airlines, 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 Saskatoon and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 6h 19m on average. Another popular route from Saskatchewan to Chicago is flying from Regina to Chicago O'Hare Intl Airport, which will take roughly 6h 35m. Keep in mind that layovers or delays could extend your travel time.

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 October 2026.

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$ 342 Cheap Flights from Saskatchewan to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

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.

12:55 p.m. - 7:58 p.m.YXE Saskatoon-ORD Chicago O'Hare Intl

7h 03m1 stop Toronto Pearson Intl

4:30 p.m. - 12:31 a.m.ORD Chicago O'Hare Intl-YXE Saskatoon

8h 01m1 stop Toronto Pearson Intl

C$ 598Air Canada

Fri, 4 Dec - Fri, 11 Dec

12:55 p.m. - 7:58 p.m.YXE Saskatoon-ORD Chicago O'Hare Intl

7h 03m1 stop Toronto Pearson Intl

3:45 p.m. - 10:41 a.m.ORD Chicago O'Hare Intl-YXE Saskatoon

18h 56m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

C$ 643Air Canada

Fri, 4 Dec - Fri, 11 Dec

12:55 p.m. - 7:58 p.m.YXE Saskatoon-ORD Chicago O'Hare Intl

7h 03m1 stop Toronto Pearson Intl

4:30 p.m. - 12:31 a.m.ORD Chicago O'Hare Intl-YXE Saskatoon

8h 01m1 stop Toronto Pearson Intl

C$ 680Air Canada

Wed, 2 Dec - Wed, 9 Dec

11:50 a.m. - 6:25 p.m.YQR Regina-ORD Chicago O'Hare Intl

6h 35m1 stop Minneapolis St Paul

11:15 a.m. - 6:40 p.m.ORD Chicago O'Hare Intl-YQR Regina

7h 25m1 stop Minneapolis St Paul

C$ 715Multiple Airlines

Fri, 13 Nov - Fri, 20 Nov

5:00 a.m. - 3:38 p.m.YQR Regina-ORD Chicago O'Hare Intl

10h 38m1 stop Toronto Pearson Intl

4:40 p.m. - 11:27 p.m.ORD Chicago O'Hare Intl-YQR Regina

6h 47m1 stop Toronto Pearson Intl

C$ 744Air Canada

Fri, 20 Nov - Sat, 28 Nov

11:50 a.m. - 7:39 p.m.YQR Regina-ORD Chicago O'Hare Intl

7h 49m1 stop Minneapolis St Paul

3:47 p.m. - 1:20 a.m.ORD Chicago O'Hare Intl-YQR Regina

9h 33m2 stops Minneapolis St Paul Calgary

C$ 753Delta

Fri, 20 Nov - Sat, 28 Nov

11:50 a.m. - 9:33 p.m.YQR Regina-ORD Chicago O'Hare Intl

9h 43m1 stop Minneapolis St Paul

9:59 a.m. - 6:40 p.m.ORD Chicago O'Hare Intl-YQR Regina

8h 41m1 stop Minneapolis St Paul

C$ 755Delta

Tue, 10 Nov - Tue, 17 Nov

11:50 a.m. - 11:54 p.m.YQR Regina-ORD Chicago O'Hare Intl

12h 04m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

9:59 a.m. - 6:40 p.m.ORD Chicago O'Hare Intl-YQR Regina

8h 41m1 stop Minneapolis St Paul

C$ 755Delta

Tue, 10 Nov - Tue, 17 Nov

11:50 a.m. - 9:33 p.m.YQR Regina-ORD Chicago O'Hare Intl

9h 43m1 stop Minneapolis St Paul

5:30 a.m. - 6:40 p.m.ORD Chicago O'Hare Intl-YQR Regina

13h 10m2 stops Atlanta Hartsfield-Jackson Minneapolis St Paul

C$ 756Delta

Tue, 10 Nov - Fri, 13 Nov

12:55 p.m. - 7:58 p.m.YXE Saskatoon-ORD Chicago O'Hare Intl

7h 03m1 stop Toronto Pearson Intl

10:30 a.m. - 12:31 a.m.ORD Chicago O'Hare Intl-YXE Saskatoon

14h 01m2 stops Minneapolis St Paul Toronto Pearson Intl

C$ 869United Airlines

Wed, 2 Dec - Wed, 9 Dec

Cheap last-minute flights

Enter your travel dates to find the best prices.

7:50 p.m. - 8:00 a.m.YXE Saskatoon-ORD Chicago O'Hare Intl

11h 10m1 stop Toronto Pearson Intl

12:59 p.m. - 6:51 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

6h 52m1 stop Toronto Pearson Intl

C$ 1,364United Airlines

Tue, 20 Oct - Wed, 21 Oct

7:50 p.m. - 8:00 a.m.YXE Saskatoon-ORD Chicago O'Hare Intl

11h 10m1 stop Toronto Pearson Intl

12:59 p.m. - 6:51 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

6h 52m1 stop Toronto Pearson Intl

C$ 1,476United Airlines

Tue, 20 Oct - Wed, 21 Oct

7:50 p.m. - 8:00 a.m.YXE Saskatoon-ORD Chicago O'Hare Intl

11h 10m1 stop Toronto Pearson Intl

10:43 a.m. - 6:51 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

9h 08m1 stop Toronto Pearson Intl

C$ 1,563Air Canada

Tue, 20 Oct - Wed, 21 Oct

7:50 p.m. - 11:21 a.m.YXE Saskatoon-ORD Chicago O'Hare Intl

14h 31m1 stop Toronto Pearson Intl

2:15 p.m. - 11:16 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

10h 01m1 stop Toronto Pearson Intl

C$ 1,607Air Canada

Tue, 20 Oct - Wed, 21 Oct

7:50 p.m. - 11:21 a.m.YXE Saskatoon-ORD Chicago O'Hare Intl

14h 31m1 stop Toronto Pearson Intl

2:15 p.m. - 11:16 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

10h 01m1 stop Toronto Pearson Intl

C$ 1,612Air Canada

Tue, 20 Oct - Wed, 21 Oct

3:10 p.m. - 9:27 p.m.YXE Saskatoon-ORD Chicago O'Hare Intl

5h 17m1 stop Minneapolis St Paul

7:00 a.m. - 11:10 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

17h 10m2 stops Detroit Metropolitan Wayne County Calgary

C$ 1,742WestJet

Tue, 20 Oct - Wed, 21 Oct

7:00 a.m. - 8:30 p.m.YXE Saskatoon-ORD Chicago O'Hare Intl

12h 30m2 stops Calgary Detroit Metropolitan Wayne County

7:00 a.m. - 11:10 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

17h 10m2 stops Detroit Metropolitan Wayne County Calgary

C$ 1,742WestJet

Tue, 20 Oct - Wed, 21 Oct

1:20 p.m. - 9:27 p.m.YXE Saskatoon-ORD Chicago O'Hare Intl

7h 07m2 stops Winnipeg Minneapolis St Paul

7:00 a.m. - 11:10 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

17h 10m2 stops Detroit Metropolitan Wayne County Calgary

C$ 1,921WestJet

Tue, 20 Oct - Wed, 21 Oct

3:10 p.m. - 9:27 p.m.YXE Saskatoon-ORD Chicago O'Hare Intl

5h 17m1 stop Minneapolis St Paul

7:00 a.m. - 11:10 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

17h 10m2 stops Detroit Metropolitan Wayne County Calgary

C$ 1,921WestJet

Tue, 20 Oct - Wed, 21 Oct

6:00 a.m. - 6:46 p.m.YXE Saskatoon-ORD Chicago O'Hare Intl

11h 46m2 stops Toronto Pearson Intl Ottawa

10:43 a.m. - 6:51 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

9h 08m1 stop Toronto Pearson Intl

C$ 2,012Air Canada

Tue, 20 Oct - Wed, 21 Oct

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Air Canada flights from Saskatchewan to Chicago

Our best Air Canada deals on Saskatchewan to Chicago flight tickets

Air Canada

4 Dec

YXE12:55 p.m.Saskatoon

7h 03m

1 stop

ORD7:58 p.m.Chicago O'Hare Intl

11 Dec

ORD4:30 p.m.Chicago O'Hare Intl

8h 01m

1 stop

YXE12:31 a.m.Saskatoon

C$ 598

Air Canada

4 Dec

YXE12:55 p.m.Saskatoon

7h 03m

1 stop

ORD7:58 p.m.Chicago O'Hare Intl

11 Dec

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

18h 56m

2 stops

YXE10:41 a.m.Saskatoon

C$ 643

Air Canada

2 Dec

YXE12:55 p.m.Saskatoon

7h 03m

1 stop

ORD7:58 p.m.Chicago O'Hare Intl

9 Dec

ORD4:30 p.m.Chicago O'Hare Intl

8h 01m

1 stop

YXE12:31 a.m.Saskatoon

C$ 680

Delta flights from Saskatchewan to Chicago

Our best Delta deals on Saskatchewan to Chicago flight tickets

Delta

20 Nov

YQR11:50 a.m.Regina

7h 49m

1 stop

ORD7:39 p.m.Chicago O'Hare Intl

28 Nov

ORD3:47 p.m.Chicago O'Hare Intl

9h 33m

2 stops

YQR1:20 a.m.Regina

C$ 753

Delta

10 Nov

YQR11:50 a.m.Regina

12h 04m

2 stops

ORD11:54 p.m.Chicago O'Hare Intl

17 Nov

ORD9:59 a.m.Chicago O'Hare Intl

8h 41m

1 stop

YQR6:40 p.m.Regina

C$ 755

Delta

10 Nov

YQR11:50 a.m.Regina

9h 43m

1 stop

ORD9:33 p.m.Chicago O'Hare Intl

13 Nov

ORD5:30 a.m.Chicago O'Hare Intl

13h 10m

2 stops

YQR6:40 p.m.Regina

C$ 756

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 4/12

12:55 p.m.-7:58 p.m.

1 stop7h 03m

Chicago O'Hare Intl

Fri 11/12

4:30 p.m.-12:31 a.m.

1 stop8h 01m

C$ 598

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 4/12

12:55 p.m.-7:58 p.m.

1 stop7h 03m

Chicago O'Hare Intl

Fri 11/12

3:45 p.m.-10:41 a.m.

2 stops18h 56m

C$ 643

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Wed 2/12

12:55 p.m.-7:58 p.m.

1 stop7h 03m

Chicago O'Hare Intl

Wed 9/12

4:30 p.m.-12:31 a.m.

1 stop8h 01m

C$ 680

Quickest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 13/11

11:50 a.m.-6:25 p.m.

1 stop6h 35m

Chicago O'Hare Intl

Fri 20/11

11:15 a.m.-6:40 p.m.

1 stop7h 25m

C$ 715

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 20/11

5:00 a.m.-3:38 p.m.

1 stop10h 38m

Chicago O'Hare Intl

Sat 28/11

4:40 p.m.-11:27 p.m.

1 stop6h 47m

C$ 744

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Fri 20/11

11:50 a.m.-7:39 p.m.

1 stop7h 49m

Chicago O'Hare Intl

Sat 28/11

3:47 p.m.-1:20 a.m.

2 stops9h 33m

C$ 753

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 10/11

11:50 a.m.-9:33 p.m.

1 stop9h 43m

Chicago O'Hare Intl

Tue 17/11

9:59 a.m.-6:40 p.m.

1 stop8h 41m

C$ 755

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 10/11

11:50 a.m.-11:54 p.m.

2 stops12h 04m

Chicago O'Hare Intl

Tue 17/11

9:59 a.m.-6:40 p.m.

1 stop8h 41m

C$ 755

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 10/11

11:50 a.m.-9:33 p.m.

1 stop9h 43m

Chicago O'Hare Intl

Fri 13/11

5:30 a.m.-6:40 p.m.

2 stops13h 10m

C$ 756

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Wed 2/12

12:55 p.m.-7:58 p.m.

1 stop7h 03m

Chicago O'Hare Intl

Wed 9/12

10:30 a.m.-12:31 a.m.

2 stops14h 01m

C$ 869

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 March is another great option to travel to Chicago, with average flight prices from Saskatchewan averaging around C$ 515.

Cheap Saskatchewan to Chicago flight deals and tips

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

Best price found	C$ 342
Fastest flight time	5h 34m
Direct flights	None

The best one-way flight to Chicago from Saskatchewan in the past 72 hours is C$ 342. The best round-trip flight deal from Saskatchewan to Chicago found on momondo in the last 72 hours is C$ 598.

The fastest flight from Saskatchewan to Chicago takes 5h 34m

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

Search flight deals

Frequently asked questions about flying 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 October 2026.
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$ 179	Free Cancellation	Rating 7.2 3,447 reviews		Search WestJet flights
United Airlines	PriceFrom C$ 436	Free Cancellation	Rating 7.4 10,384 reviews		Search United Airlines flights

Merrillville

Benton Harbor

Hammond

Munster

Valparaiso

Portage

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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.

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Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Cheap flights from Saskatchewan to Chicago from C$ 342

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Saskatchewan to Chicago departing on 5/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names, great deals

Big names, great deals

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Filter for what you want

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Air Canada flights from Saskatchewan to Chicago

Our best Air Canada deals on Saskatchewan to Chicago flight tickets

Delta flights from Saskatchewan to Chicago

Our best Delta deals on Saskatchewan to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Saskatchewan to Chicago that are best for you.

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How to get the cheapest flight ticket from Saskatchewan to Chicago

What is the cheapest month to fly to Chicago?

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

How long does it take to fly to Chicago?

Cheap Saskatchewan to Chicago flight deals and tips

Best price found

Fastest flight time

Direct flights

Frequently asked questions about flying from Saskatchewan to Chicago

Best airlines flying from Saskatchewan to Chicago

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

Travelling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago

Fly your favourite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular Cities in the United States

Popular flights according to clicks in the last 7 days on momondo

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According to popular flight searches on momondo this year

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