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: 7h 11m.

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: 60% 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: 1h 57m.

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 September 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.

$154 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.

7:00 am - 10:40 pmORD Chicago O'Hare Intl-YQR Regina

15h 40m1 stop Denver Intl

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

8h 13m1 stop Toronto Pearson Intl

$357Multiple Airlines

Sun, Nov 1 - Wed, Nov 4

4:30 pm - 10:27 pmORD Chicago O'Hare Intl-YQR Regina

6h 57m1 stop Toronto Pearson Intl

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

8h 13m1 stop Toronto Pearson Intl

$361Air Canada

Fri, Oct 30 - Wed, Nov 4

4:30 pm - 11:27 pmORD Chicago O'Hare Intl-YQR Regina

6h 57m1 stop Toronto Pearson Intl

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

8h 13m1 stop Toronto Pearson Intl

$361Air Canada

Tue, Nov 3 - Wed, Nov 4

4:30 pm - 10:27 pmORD Chicago O'Hare Intl-YQR Regina

6h 57m1 stop Toronto Pearson Intl

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

8h 13m1 stop Toronto Pearson Intl

$361Air Canada

Sat, Oct 31 - Wed, Nov 4

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

8h 40m1 stop Calgary

4:15 pm - 6:34 amYQR Regina-ORD Chicago O'Hare Intl

13h 19m2 stops Calgary Los Angeles

$364Multiple Airlines

Fri, Oct 9 - Tue, Oct 13

7:00 am - 10:40 pmORD Chicago O'Hare Intl-YQR Regina

15h 40m1 stop Denver Intl

5:00 am - 2:52 pmYQR Regina-ORD Chicago O'Hare Intl

9h 52m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

$366Multiple Airlines

Sun, Nov 1 - Wed, Nov 4

7:40 am - 11:20 pmORD Chicago O'Hare Intl-YQR Regina

16h 40m2 stops Houston George Bush Intcntl Calgary

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

7h 05m1 stop Calgary

$368Multiple Airlines

Sat, Oct 17 - Mon, Oct 19

4:30 pm - 11:27 pmORD Chicago O'Hare Intl-YQR Regina

6h 57m1 stop Toronto Pearson Intl

5:00 am - 2:52 pmYQR Regina-ORD Chicago O'Hare Intl

9h 52m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

$369Air Canada

Tue, Nov 3 - Wed, Nov 4

2:35 pm - 10:57 pmORD Chicago O'Hare Intl-YQR Regina

8h 22m1 stop Denver Intl

10:45 am - 7:05 pmYQR Regina-ORD Chicago O'Hare Intl

8h 20m1 stop Denver Intl

$428United Airlines

Wed, Dec 2 - Sun, Dec 20

4:20 pm - 9:30 pmORD Chicago O'Hare Intl-YQR Regina

6h 10m1 stop Denver Intl

9:45 am - 7:30 pmYQR Regina-ORD Chicago O'Hare Intl

8h 45m1 stop Denver Intl

$468United Airlines

Sat, Oct 3 - Tue, Oct 6

Cheap last minute flights

Enter your travel dates to find the best prices.

8:40 pm - 9:00 amORD Chicago O'Hare Intl-YQR Regina

13h 20m1 stop Toronto Pearson Intl

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

6h 38m1 stop Toronto Pearson Intl

$557Air Canada

Thu, Sep 24 - Sun, Sep 27

1:30 pm - 9:30 pmORD Chicago O'Hare Intl-YQR Regina

9h 00m1 stop Denver Intl

9:45 am - 10:46 pmYQR Regina-ORD Chicago O'Hare Intl

12h 01m1 stop Denver Intl

$740United Airlines

Thu, Sep 24 - Sun, Sep 27

12:46 pm - 9:30 pmORD Chicago O'Hare Intl-YQR Regina

9h 44m1 stop Denver Intl

9:45 am - 7:29 pmYQR Regina-ORD Chicago O'Hare Intl

8h 44m1 stop Denver Intl

$967United Airlines

Thu, Sep 24 - Sun, Sep 27

7:00 am - 9:30 pmORD Chicago O'Hare Intl-YQR Regina

15h 30m1 stop Denver Intl

9:45 am - 9:18 pmYQR Regina-ORD Chicago O'Hare Intl

10h 33m1 stop Denver Intl

$967United Airlines

Thu, Sep 24 - Sun, Sep 27

2:10 pm - 9:30 pmORD Chicago O'Hare Intl-YQR Regina

8h 20m2 stops Minneapolis St Paul Denver Intl

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

6h 38m1 stop Toronto Pearson Intl

$999United Airlines

Thu, Sep 24 - Sun, Sep 27

1:30 pm - 9:30 pmORD Chicago O'Hare Intl-YQR Regina

9h 00m1 stop Denver Intl

9:45 am - 8:40 pmYQR Regina-ORD Chicago O'Hare Intl

9h 55m2 stops Denver Intl Minneapolis St Paul

$1,001United Airlines

Thu, Sep 24 - Sun, Sep 27

2:10 pm - 9:30 pmORD Chicago O'Hare Intl-YQR Regina

8h 20m2 stops Minneapolis St Paul Denver Intl

5:45 am - 2:55 pmYQR Regina-ORD Chicago O'Hare Intl

8h 10m1 stop Toronto Pearson Intl

$1,206United Airlines

Thu, Sep 24 - Sun, Sep 27

11:17 am - 11:20 pmORD Chicago O'Hare Intl-YQR Regina

13h 03m2 stops Detroit Metropolitan Wayne County Calgary

10:45 am - 3:05 pmYQR Regina-ORD Chicago O'Hare Intl

27h 20m1 stop Minneapolis St Paul

$1,437WestJet

Thu, Sep 24 - Sun, Sep 27

11:17 am - 11:20 pmORD Chicago O'Hare Intl-YQR Regina

13h 03m2 stops Detroit Metropolitan Wayne County Calgary

8:35 am - 9:55 pmYQR Regina-ORD Chicago O'Hare Intl

12h 20m2 stops Calgary Salt Lake City

$1,701WestJet

Thu, Sep 24 - Sun, Sep 27

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United Airlines flights from Chicago to Regina

Our best United Airlines deals on Chicago to Regina flight tickets

United Airlines

Dec 2

ORD2:35 pmChicago O'Hare Intl

8h 22m

1 stop

YQR10:57 pmRegina

Dec 20

YQR10:45 amRegina

8h 20m

1 stop

ORD7:05 pmChicago O'Hare Intl

$428

United Airlines

Oct 3

ORD4:20 pmChicago O'Hare Intl

6h 10m

1 stop

YQR9:30 pmRegina

Oct 6

YQR9:45 amRegina

8h 45m

1 stop

ORD7:30 pmChicago O'Hare Intl

$468

United Airlines

Oct 1

ORD7:09 amChicago O'Hare Intl

7h 01m

1 stop

YQR1:10 pmRegina

Oct 5

YQR5:40 amRegina

6h 43m

1 stop

ORD1:23 pmChicago O'Hare Intl

$493

Delta flights from Chicago to Regina

Our best Delta deals on Chicago to Regina flight tickets

Delta

Nov 19

ORD6:49 amChicago O'Hare Intl

11h 51m

2 stops

YQR6:40 pmRegina

Nov 23

YQR11:50 amRegina

12h 04m

2 stops

ORD11:54 pmChicago O'Hare Intl

$475

Delta

Nov 19

ORD6:49 amChicago O'Hare Intl

11h 51m

2 stops

YQR6:40 pmRegina

Nov 25

YQR7:00 amRegina

13h 17m

2 stops

ORD8:17 pmChicago O'Hare Intl

$483

Delta

Oct 1

ORD8:25 amChicago O'Hare Intl

9h 55m

1 stop

YQR5:20 pmRegina

Oct 5

YQR6:00 amRegina

11h 26m

2 stops

ORD6:26 pmChicago O'Hare Intl

$520

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Sun 11/1

7:00 am-10:40 pm

1 stop15h 40m

Regina

Wed 11/4

5:00 am-1:13 pm

1 stop8h 13m

$357

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Fri 10/30

4:30 pm-10:27 pm

1 stop6h 57m

Regina

Wed 11/4

5:00 am-1:13 pm

1 stop8h 13m

$361

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Tue 11/3

4:30 pm-11:27 pm

1 stop6h 57m

Regina

Wed 11/4

5:00 am-1:13 pm

1 stop8h 13m

$361

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Sat 10/31

4:30 pm-10:27 pm

1 stop6h 57m

Regina

Wed 11/4

5:00 am-1:13 pm

1 stop8h 13m

$361

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Fri 10/9

5:30 pm-1:10 am

1 stop8h 40m

Regina

Tue 10/13

4:15 pm-6:34 am

2 stops13h 19m

$364

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Sun 11/1

7:00 am-10:40 pm

1 stop15h 40m

Regina

Wed 11/4

5:00 am-2:52 pm

2 stops9h 52m

$366

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Sat 10/17

7:40 am-11:20 pm

2 stops16h 40m

Regina

Mon 10/19

8:35 am-4:40 pm

1 stop7h 05m

$368

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Tue 11/3

4:30 pm-11:27 pm

1 stop6h 57m

Regina

Wed 11/4

5:00 am-2:52 pm

2 stops9h 52m

$369

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Wed 12/2

2:35 pm-10:57 pm

1 stop8h 22m

Regina

Sun 12/20

10:45 am-7:05 pm

1 stop8h 20m

$428

Quickest round-trip

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Sat 10/3

4:20 pm-9:30 pm

1 stop6h 10m

Regina

Tue 10/6

9:45 am-7:30 pm

1 stop8h 45m

$468

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 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?

Air Canada, United Airlines, and WestJet are the most popular carriers 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	$154
Fastest flight time	7h 01m
Direct flights	None

The best one-way flight to Regina from Chicago in the past 72 hours is $154. The best round-trip flight deal from Chicago to Regina found on momondo in the last 72 hours is $357.

The fastest flight from Chicago to Regina takes 7h 01m

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 7h 01m 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 September 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 10,214 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

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Cheap flights from Chicago to Regina from $154

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 10/2. 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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United Airlines flights from Chicago to Regina

Our best United Airlines deals on Chicago to Regina flight tickets

Delta flights from Chicago to Regina

Our best Delta 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.

Popular cities in Canada

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

Fly to other destinations from Chicago

According to popular flight searches on momondo this year

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