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Cheap flights from Chicago to Regina from $165

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 4/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Regina

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
2:20 pm - 12:55 am
ORD
-
YQR
11h 35m
1 stop
WestJet Logo
5:10 am - 1:35 pm
YQR
-
ORD
7h 25m
1 stop
$330WestJet
Fri, Apr 3 - Fri, Apr 10
WestJet Logo
5:30 pm - 11:20 pm
ORD
-
YQR
6h 50m
1 stop
WestJet Logo
7:00 am - 4:40 pm
YQR
-
ORD
8h 40m
1 stop
$369WestJet
Wed, Jun 24 - Wed, Jul 22
WestJet Logo
5:30 pm - 1:10 am
ORD
-
YQR
8h 40m
1 stop
WestJet Logo
2:00 pm - 4:40 pm
YQR
-
ORD
25h 40m
1 stop
$373WestJet
Fri, Jun 26 - Tue, Jul 14
United Airlines Logo
2:45 pm - 9:51 pm
ORD
-
YQR
8h 06m
1 stop
United Airlines Logo
9:45 am - 9:29 pm
YQR
-
ORD
10h 44m
1 stop
$380United Airlines
Wed, Mar 18 - Mon, Mar 23
WestJet Logo
5:30 pm - 1:10 am
ORD
-
YQR
8h 40m
1 stop
WestJet Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
$385WestJet
Thu, Jun 25 - Sun, Jul 19
WestJet Logo
5:30 pm - 1:10 am
ORD
-
YQR
8h 40m
1 stop
WestJet Logo
9:05 pm - 4:40 pm
YQR
-
ORD
18h 35m
1 stop
$394WestJet
Fri, Jun 19 - Sun, Jun 21
WestJet Logo
5:30 pm - 1:10 am
ORD
-
YQR
8h 40m
1 stop
WestJet Logo
6:00 am - 6:41 pm
YQR
-
ORD
11h 41m
2 stops
$403WestJet
Fri, Jun 19 - Sun, Jun 21
WestJet Logo
5:30 pm - 1:10 am
ORD
-
YQR
8h 40m
1 stop
WestJet Logo
6:00 am - 6:41 pm
YQR
-
ORD
11h 41m
2 stops
$412WestJet
Fri, Jun 19 - Sun, Jun 21
WestJet Logo
5:30 pm - 10:50 am
ORD
-
YQR
18h 20m
1 stop
WestJet Logo
9:05 pm - 4:40 pm
YQR
-
ORD
18h 35m
1 stop
$414WestJet
Tue, Jun 23 - Tue, Jul 21
WestJet Logo
5:30 pm - 11:20 pm
ORD
-
YQR
6h 50m
1 stop
WestJet Logo
6:00 am - 6:41 pm
YQR
-
ORD
11h 41m
2 stops
$415WestJet
Fri, Jun 19 - Sun, Jun 21

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
Apr 4
ORD4:15 pmChicago O'Hare Intl
7h 02m
1 stop
YQR10:17 pmRegina
Apr 11
YQR5:00 amRegina
12h 47m
2 stops
ORD6:47 pmChicago O'Hare Intl
$466
Air Canada
Apr 9
ORD6:40 pmChicago O'Hare Intl
15h 52m
1 stop
YQR9:32 amRegina
Apr 13
YQR5:00 amRegina
14h 05m
2 stops
ORD8:05 pmChicago O'Hare Intl
$536
Air Canada
Apr 9
ORD6:40 pmChicago O'Hare Intl
15h 52m
1 stop
YQR9:32 amRegina
Apr 13
YQR5:00 amRegina
7h 05m
1 stop
ORD1:05 pmChicago O'Hare Intl
$560

United Airlines flights from Chicago to Regina

Our best United Airlines deals on Chicago to Regina flight tickets
United Airlines
Mar 18
ORD2:45 pmChicago O'Hare Intl
8h 06m
1 stop
YQR9:51 pmRegina
Mar 23
YQR9:45 amRegina
10h 44m
1 stop
ORD9:29 pmChicago O'Hare Intl
$380
United Airlines
Apr 10
ORD2:35 pmChicago O'Hare Intl
7h 55m
1 stop
YQR9:30 pmRegina
Apr 15
YQR9:45 amRegina
6h 19m
1 stop
ORD5:04 pmChicago O'Hare Intl
$600
United Airlines
Mar 1
ORD7:25 amChicago O'Hare Intl
15h 26m
2 stops
YQR10:51 pmRegina
Mar 4
YQR10:45 amRegina
20h 56m
2 stops
ORD7:41 amChicago O'Hare Intl
$823

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Regina that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 19, 2026.
Use the filters below to find and compare flights from Chicago to Regina that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 4/3

2:20 pm-12:55 am

1 stop11h 35m

Regina

Fri 4/10

5:10 am-1:35 pm

1 stop7h 25m

$330

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 6/24

5:30 pm-11:20 pm

1 stop6h 50m

Regina

Wed 7/22

7:00 am-4:40 pm

1 stop8h 40m

$369

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/26

5:30 pm-1:10 am

1 stop8h 40m

Regina

Tue 7/14

2:00 pm-4:40 pm

1 stop25h 40m

$373

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 3/18

2:45 pm-9:51 pm

1 stop8h 06m

Regina

Mon 3/23

9:45 am-9:29 pm

1 stop10h 44m

$380

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 6/25

5:30 pm-1:10 am

1 stop8h 40m

Regina

Sun 7/19

8:35 am-4:40 pm

1 stop7h 05m

$385

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

5:30 pm-1:10 am

1 stop8h 40m

Regina

Sun 6/21

9:05 pm-4:40 pm

1 stop18h 35m

$394

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

5:30 pm-1:10 am

1 stop8h 40m

Regina

Sun 6/21

6:00 am-6:41 pm

2 stops11h 41m

$403

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

5:30 pm-1:10 am

1 stop8h 40m

Regina

Sun 6/21

6:00 am-6:41 pm

2 stops11h 41m

$412

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 6/23

5:30 pm-10:50 am

1 stop18h 20m

Regina

Tue 7/21

9:05 pm-4:40 pm

1 stop18h 35m

$414

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

5:30 pm-11:20 pm

1 stop6h 50m

Regina

Sun 6/21

6:00 am-6:41 pm

2 stops11h 41m

$415

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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See travel insights to Regina from

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

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

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

Fastest flight time

8h 25m

Direct flights

None
The fastest flight from Chicago to Regina takes 8h 25m
There are no direct flights from Chicago to Regina. There are no popular flight routes from Chicago to Regina.
Search flight deals

  • 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 25m 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?

  • 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?

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 AirlinesPriceFrom $284Free CancellationRating
7.4
9,322 reviews
Search United Airlines flights
WestJetPriceFrom $328Free CancellationRating
7.2
3,268 reviews
Search WestJet flights

Traveling to a place near Regina?

Book flights to Regina if you plan to visit one of these locations
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.

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