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

WestJet, Air Canada, and United Airlines 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 7h 47m on average. Another popular route from Saskatchewan to Chicago is flying from Saskatoon to Chicago O'Hare Intl Airport, which will take roughly 10h 26m. 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 is 1 operator available for flights from Saskatchewan to Chicago as of September 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$ 200 Cheap Flights from Saskatchewan to Chicago in 2026

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.

7:50 p.m. - 1:23 p.m.YXE Saskatoon-ORD Chicago O'Hare Intl

16h 33m1 stop Toronto Pearson Intl

3:45 p.m. - 11:16 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

8h 31m1 stop Toronto Pearson Intl

C$ 392Air Canada

Fri, 16 Oct - Fri, 23 Oct

9:05 p.m. - 4:40 p.m.YQR Regina-ORD Chicago O'Hare Intl

18h 35m1 stop Calgary

5:30 p.m. - 1:10 a.m.ORD Chicago O'Hare Intl-YQR Regina

8h 40m1 stop Calgary

C$ 411WestJet

Wed, 14 Oct - Mon, 19 Oct

9:45 a.m. - 6:32 p.m.YQR Regina-ORD Chicago O'Hare Intl

7h 47m1 stop Denver Intl

5:55 a.m. - 9:30 p.m.ORD Chicago O'Hare Intl-YQR Regina

16h 35m1 stop Denver Intl

C$ 422United Airlines

Tue, 22 Sep - Wed, 23 Sep

9:45 a.m. - 6:32 p.m.YQR Regina-ORD Chicago O'Hare Intl

7h 47m1 stop Denver Intl

5:55 a.m. - 9:30 p.m.ORD Chicago O'Hare Intl-YQR Regina

16h 35m1 stop Denver Intl

C$ 432United Airlines

Tue, 22 Sep - Wed, 23 Sep

10:45 a.m. - 11:59 p.m.YQR Regina-ORD Chicago O'Hare Intl

13h 14m1 stop Denver Intl

8:40 p.m. - 10:43 a.m.ORD Chicago O'Hare Intl-YQR Regina

14h 03m1 stop Toronto Pearson Intl

C$ 435Multiple Airlines

Sat, 21 Nov - Sat, 28 Nov

9:45 a.m. - 6:32 p.m.YQR Regina-ORD Chicago O'Hare Intl

7h 47m1 stop Denver Intl

5:55 a.m. - 9:30 p.m.ORD Chicago O'Hare Intl-YQR Regina

16h 35m1 stop Denver Intl

C$ 437United Airlines

Tue, 22 Sep - Wed, 23 Sep

7:00 a.m. - 6:26 p.m.YXE Saskatoon-ORD Chicago O'Hare Intl

10h 26m2 stops Calgary Detroit Metropolitan Wayne County

5:30 p.m. - 1:00 a.m.ORD Chicago O'Hare Intl-YXE Saskatoon

8h 30m1 stop Calgary

C$ 456Delta

Thu, 1 Oct - Thu, 8 Oct

7:50 p.m. - 9:00 a.m.YXE Saskatoon-ORD Chicago O'Hare Intl

12h 10m1 stop Toronto Pearson Intl

3:45 p.m. - 11:16 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

8h 31m1 stop Toronto Pearson Intl

C$ 458Air Canada

Mon, 28 Sep - Tue, 29 Sep

7:50 p.m. - 9:00 a.m.YXE Saskatoon-ORD Chicago O'Hare Intl

12h 10m1 stop Toronto Pearson Intl

4:30 p.m. - 11:31 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

8h 01m1 stop Toronto Pearson Intl

C$ 462Air Canada

Fri, 23 Oct - Wed, 28 Oct

3:30 p.m. - 4:40 p.m.YXE Saskatoon-ORD Chicago O'Hare Intl

48h 10m2 stops Edmonton Calgary

5:30 p.m. - 1:00 a.m.ORD Chicago O'Hare Intl-YXE Saskatoon

8h 30m1 stop Calgary

C$ 464WestJet

Fri, 16 Oct - Fri, 23 Oct

Cheap last-minute flights

Enter your travel dates to find the best prices.

10:45 a.m. - 11:59 p.m.YQR Regina-ORD Chicago O'Hare Intl

12h 14m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

5:30 p.m. - 1:10 a.m.ORD Chicago O'Hare Intl-YQR Regina

8h 40m1 stop Calgary

C$ 851Multiple Airlines

Tue, 8 Sep - Fri, 11 Sep

10:45 a.m. - 9:33 p.m.YQR Regina-ORD Chicago O'Hare Intl

9h 48m1 stop Minneapolis St Paul

12:29 p.m. - 1:10 a.m.ORD Chicago O'Hare Intl-YQR Regina

13h 41m2 stops Minneapolis St Paul Calgary

C$ 857Delta

Tue, 8 Sep - Fri, 11 Sep

10:45 a.m. - 9:33 p.m.YQR Regina-ORD Chicago O'Hare Intl

9h 48m1 stop Minneapolis St Paul

5:30 p.m. - 1:10 a.m.ORD Chicago O'Hare Intl-YQR Regina

8h 40m1 stop Calgary

C$ 862Multiple Airlines

Tue, 8 Sep - Fri, 11 Sep

10:45 a.m. - 11:59 p.m.YQR Regina-ORD Chicago O'Hare Intl

12h 14m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

8:55 a.m. - 12:35 a.m.ORD Chicago O'Hare Intl-YQR Regina

16h 40m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

C$ 919Delta

Tue, 8 Sep - Fri, 11 Sep

10:45 a.m. - 11:59 p.m.YQR Regina-ORD Chicago O'Hare Intl

12h 14m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

8:55 a.m. - 12:35 a.m.ORD Chicago O'Hare Intl-YQR Regina

16h 40m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

C$ 924Delta

Tue, 8 Sep - Fri, 11 Sep

7:55 p.m. - 8:00 a.m.YXE Saskatoon-ORD Chicago O'Hare Intl

11h 05m1 stop Toronto Pearson Intl

1:55 p.m. - 11:39 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

10h 44m2 stops Ottawa Toronto Pearson Intl

C$ 1,578Air Canada

Fri, 4 Sep - Mon, 7 Sep

6:00 a.m. - 2:55 p.m.YXE Saskatoon-ORD Chicago O'Hare Intl

7h 55m1 stop Toronto Pearson Intl

10:43 a.m. - 11:39 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

13h 56m1 stop Toronto Pearson Intl

C$ 1,666United Airlines

Fri, 4 Sep - Mon, 7 Sep

7:00 a.m. - 6:29 p.m.YXE Saskatoon-ORD Chicago O'Hare Intl

10h 29m2 stops Calgary Detroit Metropolitan Wayne County

6:00 a.m. - 5:40 p.m.ORD Chicago O'Hare Intl-YXE Saskatoon

12h 40m2 stops Minneapolis St Paul Vancouver Intl

C$ 1,865WestJet

Fri, 4 Sep - Mon, 7 Sep

8:55 p.m. - 3:44 p.m.YXE Saskatoon-MDW Chicago Midway

17h 49m2 stops Calgary Atlanta Hartsfield-Jackson

6:42 p.m. - 5:40 p.m.MDW Chicago Midway-YXE Saskatoon

23h 58m2 stops Detroit Metropolitan Wayne County Vancouver Intl

C$ 1,865WestJet

Fri, 4 Sep - Mon, 7 Sep

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United Airlines flights from Saskatchewan to Chicago

Our best United Airlines deals on Saskatchewan to Chicago flight tickets

United Airlines

22 Sep

YQR9:45 a.m.Regina

7h 47m

1 stop

ORD6:32 p.m.Chicago O'Hare Intl

23 Sep

ORD5:55 a.m.Chicago O'Hare Intl

16h 35m

1 stop

YQR9:30 p.m.Regina

C$ 422

United Airlines

22 Sep

YQR9:45 a.m.Regina

7h 47m

1 stop

ORD6:32 p.m.Chicago O'Hare Intl

23 Sep

ORD5:55 a.m.Chicago O'Hare Intl

16h 35m

1 stop

YQR9:30 p.m.Regina

C$ 432

United Airlines

22 Sep

YQR9:45 a.m.Regina

7h 47m

1 stop

ORD6:32 p.m.Chicago O'Hare Intl

23 Sep

ORD5:55 a.m.Chicago O'Hare Intl

16h 35m

1 stop

YQR9:30 p.m.Regina

C$ 437

Air Canada flights from Saskatchewan to Chicago

Our best Air Canada deals on Saskatchewan to Chicago flight tickets

Air Canada

16 Oct

YXE7:50 p.m.Saskatoon

16h 33m

1 stop

ORD1:23 p.m.Chicago O'Hare Intl

23 Oct

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

8h 31m

1 stop

YXE11:16 p.m.Saskatoon

C$ 392

Air Canada

28 Sep

YXE7:50 p.m.Saskatoon

12h 10m

1 stop

ORD9:00 a.m.Chicago O'Hare Intl

29 Sep

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

8h 31m

1 stop

YXE11:16 p.m.Saskatoon

C$ 458

Air Canada

23 Oct

YXE7:50 p.m.Saskatoon

12h 10m

1 stop

ORD9:00 a.m.Chicago O'Hare Intl

28 Oct

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

8h 01m

1 stop

YXE11:31 p.m.Saskatoon

C$ 462

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 16/10

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

1 stop16h 33m

Chicago O'Hare Intl

Fri 23/10

3:45 p.m.-11:16 p.m.

1 stop8h 31m

C$ 392

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Wed 14/10

9:05 p.m.-4:40 p.m.

1 stop18h 35m

Chicago O'Hare Intl

Mon 19/10

5:30 p.m.-1:10 a.m.

1 stop8h 40m

C$ 411

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 22/9

9:45 a.m.-6:32 p.m.

1 stop7h 47m

Chicago O'Hare Intl

Wed 23/9

5:55 a.m.-9:30 p.m.

1 stop16h 35m

C$ 422

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 22/9

9:45 a.m.-6:32 p.m.

1 stop7h 47m

Chicago O'Hare Intl

Wed 23/9

5:55 a.m.-9:30 p.m.

1 stop16h 35m

C$ 432

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Sat 21/11

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

1 stop13h 14m

Chicago O'Hare Intl

Sat 28/11

8:40 p.m.-10:43 a.m.

1 stop14h 03m

C$ 435

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 22/9

9:45 a.m.-6:32 p.m.

1 stop7h 47m

Chicago O'Hare Intl

Wed 23/9

5:55 a.m.-9:30 p.m.

1 stop16h 35m

C$ 437

Quickest round-trip

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Thu 1/10

7:00 a.m.-6:26 p.m.

2 stops10h 26m

Chicago O'Hare Intl

Thu 8/10

5:30 p.m.-1:00 a.m.

1 stop8h 30m

C$ 456

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Mon 28/9

7:50 p.m.-9:00 a.m.

1 stop12h 10m

Chicago O'Hare Intl

Tue 29/9

3:45 p.m.-11:16 p.m.

1 stop8h 31m

C$ 458

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 23/10

7:50 p.m.-9:00 a.m.

1 stop12h 10m

Chicago O'Hare Intl

Wed 28/10

4:30 p.m.-11:31 p.m.

1 stop8h 01m

C$ 462

SaskatoonChicago

YXE Saskatoon - ORD Chicago O'Hare Intl

YXEORD

Saskatoon

Fri 16/10

3:30 p.m.-4:40 p.m.

2 stops48h 10m

Chicago O'Hare Intl

Fri 23/10

5:30 p.m.-1:00 a.m.

1 stop8h 30m

C$ 464

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 November is another great option to travel to Chicago, with average flight prices from Saskatchewan averaging around C$ 483.

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$ 200
Fastest flight time	7h 47m
Direct flights	None

The best one-way flight to Chicago from Saskatchewan in the past 72 hours is C$ 200. The best round-trip flight deal from Saskatchewan to Chicago found on momondo in the last 72 hours is C$ 392.

The fastest flight from Saskatchewan to Chicago takes 7h 47m

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 is 1 operator available for flights from Saskatchewan to Chicago as of September 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$ 176	Free Cancellation	Rating 7.2 3,446 reviews		Search WestJet 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$ 200

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 11/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Saskatchewan to Chicago

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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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United Airlines flights from Saskatchewan to Chicago

Our best United Airlines deals on Saskatchewan to Chicago flight tickets

Air Canada flights from Saskatchewan to Chicago

Our best Air Canada 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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