What airlines fly to Regina?

WestJet, Delta and United Airlines are the top three most popular airlines that fly to Regina from Chicago according to our data. WestJet is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Regina. Keep in mind that there are 3 different airlines that fly to Regina on a routine basis, so you have a few additional options to choose from.

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

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

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

Prices for flights from Chicago to Regina Airport refresh daily.

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

As of July 2025, there are 2 operators available to choose from for flights from Chicago to Regina Airport.

How old do you have to be to fly from Chicago to Regina Airport?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Regina Airport.

What documentation or ID do you need to fly to Regina Airport?

The necessary travel and health documents for your Regina Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$119 Cheap Flights from Chicago to Regina in 2025

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Find the cheapest flights from Chicago to Regina

Round-trip

One-way

Cheap round-trip flights

5:30 pm - 1:07 amORD-YQR

8h 37m1 stop

6:55 am - 4:43 pmYQR-ORD

8h 48m1 stop

$286WestJet

Find Deal

Wed, Aug 27 - Wed, Sep 3

5:30 pm - 1:07 amORD-YQR

8h 37m1 stop

6:55 am - 4:43 pmYQR-ORD

8h 48m1 stop

$304WestJet

Find Deal

Tue, Aug 26 - Tue, Sep 2

5:30 pm - 1:07 amORD-YQR

8h 37m1 stop

6:55 am - 4:43 pmYQR-ORD

8h 48m1 stop

$312WestJet

Find Deal

Tue, Aug 26 - Tue, Sep 2

5:30 pm - 11:02 pmORD-YQR

6h 32m1 stop

11:45 am - 4:43 pmYQR-ORD

27h 58m1 stop

$314WestJet

Find Deal

Wed, Aug 27 - Wed, Sep 3

5:30 pm - 9:30 amORD-YQR

17h 00m2 stops

8:35 am - 4:43 pmYQR-ORD

7h 08m1 stop

$319WestJet

Find Deal

Wed, Aug 27 - Wed, Sep 3

3:55 pm - 11:19 pmORD-YQR

7h 24m1 stop

5:00 am - 1:01 pmYQR-ORD

8h 01m1 stop

$326Air Canada

Find Deal

Thu, Nov 6 - Tue, Nov 11

5:30 pm - 9:30 amORD-YQR

17h 00m2 stops

8:35 am - 4:43 pmYQR-ORD

7h 08m1 stop

$330WestJet

Find Deal

Wed, Aug 27 - Wed, Sep 3

3:55 pm - 11:19 pmORD-YQR

7h 24m1 stop

5:00 am - 2:55 pmYQR-ORD

9h 55m2 stops

$331Air Canada

Find Deal

Thu, Nov 6 - Tue, Nov 11

5:30 pm - 1:07 amORD-YQR

8h 37m1 stop

11:45 am - 9:51 amYQR-ORD

21h 06m2 stops

$341

Find Deal

Tue, Aug 26 - Tue, Sep 2

7:15 am - 11:19 pmORD-YQR

16h 04m2 stops

5:00 am - 2:55 pmYQR-ORD

9h 55m2 stops

$360Air Canada

Find Deal

Thu, Nov 6 - Tue, Nov 11

WestJet flights from Chicago to Regina

Our best WestJet deals on Chicago to Regina flight tickets

WestJet

Aug 27

ORD5:30 pmChicago O'Hare Intl

8h 37m

1 stop

YQR1:07 amRegina

Sep 3

YQR6:55 amRegina

8h 48m

1 stop

ORD4:43 pmChicago O'Hare Intl

$286

Find similar

WestJet

Aug 26

ORD5:30 pmChicago O'Hare Intl

8h 37m

1 stop

YQR1:07 amRegina

Sep 2

YQR6:55 amRegina

8h 48m

1 stop

ORD4:43 pmChicago O'Hare Intl

$304

Find similar

WestJet

Aug 26

ORD5:30 pmChicago O'Hare Intl

8h 37m

1 stop

YQR1:07 amRegina

Sep 2

YQR6:55 amRegina

8h 48m

1 stop

ORD4:43 pmChicago O'Hare Intl

$312

Find similar

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets

Air Canada

Nov 6

ORD3:55 pmChicago O'Hare Intl

7h 24m

1 stop

YQR11:19 pmRegina

Nov 11

YQR5:00 amRegina

8h 01m

1 stop

ORD1:01 pmChicago O'Hare Intl

$326

Find similar

Air Canada

Nov 6

ORD3:55 pmChicago O'Hare Intl

7h 24m

1 stop

YQR11:19 pmRegina

Nov 11

YQR5:00 amRegina

9h 55m

2 stops

ORD2:55 pmChicago O'Hare Intl

$331

Find similar

Air Canada

Nov 6

ORD7:15 amChicago O'Hare Intl

16h 04m

2 stops

YQR11:19 pmRegina

Nov 11

YQR5:00 amRegina

9h 55m

2 stops

ORD2:55 pmChicago O'Hare Intl

$360

Find similar

How to get the cheapest flight ticket from Chicago to Regina

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

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

The cheapest day to depart from Chicago to Regina is on a Wednesday when prices can be found for as low as $348. Flights from Chicago to Regina on a Sunday will generally be more expensive and average around $1,034. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

The cheapest time of day to fly to Regina is in the afternoon when flights can be purchased for as low as $283. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $576 on average. Flights to Regina from Chicago in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

When to book flights from Chicago to Regina

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Regina according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Regina (CHI to YQR) flight deals and tips

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

Best Price Found	$119
Fastest flight time	6h 32m
Direct flights	None
Airports in Regina	1 airport

The best one-way flight to Regina from Chicago in the past 72 hours is $119. The best round-trip flight deal from Chicago to Regina found on momondo in the last 72 hours is $286.

The fastest flight from Chicago to Regina takes 6h 32m

There are no direct flights from Chicago to Regina. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - Regina Airport.

There is 1 airport near Regina: Regina (YQR)

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How far is Chicago to Regina by plane?
The straight-line distance from Chicago to Regina is 1001.4 mi. Typically, this will take 6h 32m by plane in normal conditions.
When did momondo last update prices for flights from Chicago to Regina Airport?
Prices for flights from Chicago to Regina Airport refresh daily.
How many operators does momondo search for flights from Chicago to Regina Airport?
As of July 2025, there are 2 operators available to choose from for flights from Chicago to Regina Airport.
How old do you have to be to fly from Chicago to Regina Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Regina Airport.
What documentation or ID do you need to fly to Regina Airport?
The necessary travel and health documents for your Regina Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular airline from Chicago to Regina?
momondo data reveals that the most frequently booked airline on the route from Chicago to Regina is Delta, representing 54% of all bookings. The subsequent popular airline is WestJet at 46%.

Best airlines flying from Chicago to Regina

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

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $284	Free Cancellation	Rating 7.4 8,856 reviews	Search United Airlines flights
WestJet	PriceFrom $328	Free Cancellation	Rating 7.2 2,939 reviews	Search WestJet flights
Delta	PriceFrom $517	Free Cancellation	Rating 8.0 7,953 reviews	Search Delta flights

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Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Regina for you.

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

Flights from Chicago to Regina 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 Chicago to Regina?

momondo helps you find the best flight between Chicago and Regina by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

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