Which layover airport offers the lowest fares from Chicago to Regina?

Flights via Calgary (YYC) offer the lowest average round-trip price of $502.

Which airport is the most popular layover for flights between Chicago and Regina?

Denver (DEN) was the most common stop: 57% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport has the shortest connection time from Chicago to Regina?

Toronto (YYZ) has the shortest average layover time for this route: 2h 25m.

Which layover airport has the shortest travel time from Chicago to Regina?

Flights connecting via Toronto (YYZ) have the shortest average one-way travel time: 8h 22m.

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 October 2026, there is 1 operator 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.

$489 Cheap Flights from Chicago to Regina in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Regina

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:05 am - 6:40 pmORD Chicago O'Hare Intl-YQR Regina

7h 35m1 stop Minneapolis St Paul

11:50 am - 12:26 amYQR Regina-ORD Chicago O'Hare Intl

36h 36m2 stops Minneapolis St Paul Denver Intl

$525Multiple Airlines

Wed, Dec 23 - Tue, Jan 5

8:40 pm - 10:43 amORD Chicago O'Hare Intl-YQR Regina

14h 03m1 stop Toronto Pearson Intl

5:00 am - 1:13 pmYQR Regina-ORD Chicago O'Hare Intl

8h 13m1 stop Toronto Pearson Intl

$558Air Canada

Wed, Nov 18 - Mon, Nov 23

8:40 pm - 10:43 amORD Chicago O'Hare Intl-YQR Regina

14h 03m1 stop Toronto Pearson Intl

5:00 am - 1:13 pmYQR Regina-ORD Chicago O'Hare Intl

8h 13m1 stop Toronto Pearson Intl

$558Air Canada

Wed, Nov 18 - Tue, Nov 24

11:05 am - 6:40 pmORD Chicago O'Hare Intl-YQR Regina

7h 35m1 stop Minneapolis St Paul

11:50 am - 12:26 amYQR Regina-ORD Chicago O'Hare Intl

36h 36m2 stops Minneapolis St Paul Denver Intl

$558Multiple Airlines

Wed, Dec 23 - Mon, Jan 4

8:40 pm - 10:43 amORD Chicago O'Hare Intl-YQR Regina

14h 03m1 stop Toronto Pearson Intl

5:00 am - 3:02 pmYQR Regina-ORD Chicago O'Hare Intl

10h 02m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

$567Air Canada

Wed, Nov 18 - Tue, Nov 24

8:40 pm - 10:43 amORD Chicago O'Hare Intl-YQR Regina

14h 03m1 stop Toronto Pearson Intl

5:00 am - 3:00 pmYQR Regina-ORD Chicago O'Hare Intl

10h 00m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

$567Air Canada

Wed, Nov 18 - Mon, Nov 23

10:00 am - 6:40 pmORD Chicago O'Hare Intl-YQR Regina

8h 40m1 stop Minneapolis St Paul

7:00 am - 5:40 pmYQR Regina-ORD Chicago O'Hare Intl

10h 40m1 stop Toronto Pearson Intl

$573Multiple Airlines

Wed, Nov 25 - Sat, Nov 28

8:40 pm - 9:43 amORD Chicago O'Hare Intl-YQR Regina

14h 03m1 stop Toronto Pearson Intl

5:00 am - 3:38 pmYQR Regina-ORD Chicago O'Hare Intl

10h 38m1 stop Toronto Pearson Intl

$589Air Canada

Fri, Oct 30 - Wed, Nov 4

2:30 pm - 10:40 pmORD Chicago O'Hare Intl-YQR Regina

8h 10m1 stop Denver Intl

10:45 am - 10:46 pmYQR Regina-ORD Chicago O'Hare Intl

12h 01m1 stop Denver Intl

$601United Airlines

Wed, Nov 18 - Mon, Nov 23

2:30 pm - 10:40 pmORD Chicago O'Hare Intl-YQR Regina

8h 10m1 stop Denver Intl

10:45 am - 10:46 pmYQR Regina-ORD Chicago O'Hare Intl

12h 01m1 stop Denver Intl

$633United Airlines

Wed, Nov 18 - Mon, Nov 23

Cheap last minute flights

Enter your travel dates to find the best prices.

9:20 pm - 9:00 amORD Chicago O'Hare Intl-YQR Regina

12h 40m1 stop Toronto Pearson Intl

4:00 am - 11:57 amYQR Regina-ORD Chicago O'Hare Intl

6h 57m1 stop Toronto Pearson Intl

$1,013Air Canada

Fri, Oct 23 - Wed, Oct 28

3:40 pm - 9:00 amORD Chicago O'Hare Intl-YQR Regina

18h 20m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

4:00 am - 11:57 amYQR Regina-ORD Chicago O'Hare Intl

6h 57m1 stop Toronto Pearson Intl

$1,021Air Canada

Fri, Oct 23 - Wed, Oct 28

5:30 pm - 1:10 amORD Chicago O'Hare Intl-YQR Regina

8h 40m1 stop Calgary

6:00 am - 5:40 amYQR Regina-ORD Chicago O'Hare Intl

22h 40m2 stops Calgary Seattle/Tacoma Intl

$1,034Multiple Airlines

Thu, Oct 22 - Fri, Oct 23

12:30 pm - 1:10 amORD Chicago O'Hare Intl-YQR Regina

13h 40m3 stops Quincy Regional Nashville Intl Calgary

6:00 am - 4:40 pmYQR Regina-ORD Chicago O'Hare Intl

9h 40m1 stop Calgary

$1,128Multiple Airlines

Thu, Oct 22 - Fri, Oct 23

12:30 pm - 1:10 amORD Chicago O'Hare Intl-YQR Regina

13h 40m3 stops Quincy Regional Nashville Intl Calgary

2:00 pm - 12:24 amYQR Regina-ORD Chicago O'Hare Intl

33h 24m3 stops Calgary Phoenix Sky Harbor Intl Denver Intl

$1,167Multiple Airlines

Thu, Oct 22 - Fri, Oct 23

5:30 pm - 7:45 pmORD Chicago O'Hare Intl-YQR Regina

27h 15m2 stops Calgary Edmonton

7:25 pm - 12:13 pmYQR Regina-ORD Chicago O'Hare Intl

15h 48m2 stops Calgary Atlanta Hartsfield-Jackson

$1,207WestJet

Fri, Oct 23 - Wed, Oct 28

6:20 am - 5:20 pmORD Chicago O'Hare Intl-YQR Regina

12h 00m1 stop Minneapolis St Paul

8:35 am - 4:40 pmYQR Regina-ORD Chicago O'Hare Intl

7h 05m1 stop Calgary

$1,213WestJet

Thu, Oct 22 - Fri, Oct 23

3:30 pm - 11:55 amORD Chicago O'Hare Intl-YQR Regina

21h 25m2 stops Las Vegas Harry Reid Intl Vancouver Intl

2:00 pm - 7:07 pmYQR Regina-ORD Chicago O'Hare Intl

28h 07m3 stops Calgary Phoenix Sky Harbor Intl Dallas/Fort Worth

$1,250Multiple Airlines

Thu, Oct 22 - Fri, Oct 23

6:10 am - 10:50 amORD Chicago O'Hare Intl-YQR Regina

29h 40m2 stops Cancun Calgary

6:00 am - 11:32 amYQR Regina-ORD Chicago O'Hare Intl

28h 32m3 stops Calgary San Francisco Atlanta Hartsfield-Jackson

$1,344Multiple Airlines

Sun, Oct 18 - Tue, Oct 20

7:09 am - 1:10 pmORD Chicago O'Hare Intl-YQR Regina

7h 01m1 stop Toronto Pearson Intl

5:45 am - 1:23 pmYQR Regina-ORD Chicago O'Hare Intl

6h 38m1 stop Toronto Pearson Intl

$1,451United Airlines

Sun, Oct 18 - Tue, Oct 20

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Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets

Air Canada

Nov 18

ORD8:40 pmChicago O'Hare Intl

14h 03m

1 stop

YQR10:43 amRegina

Nov 23

YQR5:00 amRegina

8h 13m

1 stop

ORD1:13 pmChicago O'Hare Intl

$558

Air Canada

Nov 18

ORD8:40 pmChicago O'Hare Intl

14h 03m

1 stop

YQR10:43 amRegina

Nov 23

YQR5:00 amRegina

10h 00m

2 stops

ORD3:00 pmChicago O'Hare Intl

$567

Air Canada

Oct 30

ORD8:40 pmChicago O'Hare Intl

14h 03m

1 stop

YQR9:43 amRegina

Nov 4

YQR5:00 amRegina

10h 38m

1 stop

ORD3:38 pmChicago O'Hare Intl

$589

United Airlines flights from Chicago to Regina

Our best United Airlines deals on Chicago to Regina flight tickets

United Airlines

Nov 18

ORD2:30 pmChicago O'Hare Intl

8h 10m

1 stop

YQR10:40 pmRegina

Nov 23

YQR10:45 amRegina

12h 01m

1 stop

ORD10:46 pmChicago O'Hare Intl

$601

United Airlines

Nov 18

ORD2:30 pmChicago O'Hare Intl

8h 10m

1 stop

YQR10:40 pmRegina

Nov 23

YQR10:45 amRegina

12h 01m

1 stop

ORD10:46 pmChicago O'Hare Intl

$633

United Airlines

Oct 18

ORD7:09 amChicago O'Hare Intl

7h 01m

1 stop

YQR1:10 pmRegina

Oct 20

YQR5:45 amRegina

6h 38m

1 stop

ORD1:23 pmChicago O'Hare Intl

$1,451

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Wed 12/23

11:05 am-6:40 pm

1 stop7h 35m

Regina

Tue 1/5

11:50 am-12:26 am

2 stops36h 36m

$525

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Wed 11/18

8:40 pm-10:43 am

1 stop14h 03m

Regina

Mon 11/23

5:00 am-1:13 pm

1 stop8h 13m

$558

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Wed 11/18

8:40 pm-10:43 am

1 stop14h 03m

Regina

Tue 11/24

5:00 am-1:13 pm

1 stop8h 13m

$558

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Wed 12/23

11:05 am-6:40 pm

1 stop7h 35m

Regina

Mon 1/4

11:50 am-12:26 am

2 stops36h 36m

$558

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Wed 11/18

8:40 pm-10:43 am

1 stop14h 03m

Regina

Tue 11/24

5:00 am-3:02 pm

2 stops10h 02m

$567

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Wed 11/18

8:40 pm-10:43 am

1 stop14h 03m

Regina

Mon 11/23

5:00 am-3:00 pm

2 stops10h 00m

$567

Quickest round-trip

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Wed 11/25

10:00 am-6:40 pm

1 stop8h 40m

Regina

Sat 11/28

7:00 am-5:40 pm

1 stop10h 40m

$573

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Fri 10/30

8:40 pm-9:43 am

1 stop14h 03m

Regina

Wed 11/4

5:00 am-3:38 pm

1 stop10h 38m

$589

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Wed 11/18

2:30 pm-10:40 pm

1 stop8h 10m

Regina

Mon 11/23

10:45 am-10:46 pm

1 stop12h 01m

$601

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Wed 11/18

2:30 pm-10:40 pm

1 stop8h 10m

Regina

Mon 11/23

10:45 am-10:46 pm

1 stop12h 01m

$633

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first

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

Airlines

Layovers

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

WestJet is the most popular carrier operating from Chicago to Regina

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	$489
Fastest flight time	8h 10m
Direct flights	None

The best one-way flight to Regina from Chicago in the past 72 hours is $489. The best round-trip flight deal from Chicago to Regina found on momondo in the last 72 hours is $525.

The fastest flight from Chicago to Regina takes 8h 10m

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

Search flight deals

Frequently asked questions about flying from Chicago to Regina

How far is Chicago to Regina by plane?
The straight-line distance from Chicago to Regina is 1001.4 mi. Typically, this will take 8h 10m 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 October 2026, there is 1 operator 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.

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 $213	Free Cancellation	Rating 7.4 10,382 reviews		Search United Airlines flights

Moose Jaw

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.

An easier way to manage your Regina 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.

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Cheap flights from Chicago to Regina from $489

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Regina departing on 10/23. 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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Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets

United Airlines flights from Chicago to Regina

Our best United Airlines deals on Chicago to Regina flight tickets

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How to get the cheapest flight ticket from Chicago to Regina

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

Which airport is the most popular layover for flights between Chicago and Regina?

Which layover airport offers the lowest fares from Chicago to Regina?

Which layover airport has the shortest travel time from Chicago to Regina?

Which layover airport has the shortest connection time from Chicago to Regina?

When to book flights from Chicago to Regina

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

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Chicago to Regina

Best airlines flying from Chicago to Regina

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

Traveling to a place near Regina?

Why use momondo?

An easier way to manage your Regina 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 Canada

Airports servicing Saskatchewan

Fly your favorite airline to Regina

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

Cabin classes currently available on flights to Regina

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

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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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