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Cheap flights from Chicago to Regina from $116

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 5/30. 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.
Air Canada Logo
6:40 pm - 9:32 am
ORD
-
YQR
15h 52m
1 stop
Air Canada Logo
5:45 am - 2:55 pm
YQR
-
ORD
8h 10m
1 stop
$342Air Canada
Wed, Apr 29 - Sat, May 2
Air Canada Logo
6:40 pm - 9:32 am
ORD
-
YQR
15h 52m
1 stop
Air Canada Logo
5:45 am - 8:08 pm
YQR
-
ORD
13h 23m
2 stops
$350Air Canada
Wed, Apr 29 - Sat, May 2
Air Canada Logo
6:40 pm - 9:32 am
ORD
-
YQR
15h 52m
1 stop
Air Canada Logo
5:45 am - 1:25 pm
YQR
-
ORD
6h 40m
1 stop
$353Air Canada
Wed, Apr 29 - Sat, May 2
Multiple Airlines Logo
7:13 pm - 6:21 pm
ORD
-
YQR
24h 08m
1 stop
Multiple Airlines Logo
7:00 am - 4:40 pm
YQR
-
ORD
8h 40m
1 stop
$356Multiple Airlines
Thu, Apr 23 - Thu, Apr 30
Air Canada Logo
6:40 pm - 9:32 am
ORD
-
YQR
15h 52m
1 stop
Air Canada Logo
5:45 am - 8:08 pm
YQR
-
ORD
13h 23m
2 stops
$361Air Canada
Wed, Apr 29 - Sat, May 2
Multiple Airlines Logo
7:05 pm - 6:21 pm
ORD
-
YQR
24h 16m
1 stop
Multiple Airlines Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
$363Multiple Airlines
Mon, Apr 20 - Mon, Apr 27
Air Canada Logo
8:40 pm - 9:05 am
ORD
-
YQR
13h 25m
1 stop
Air Canada Logo
5:45 am - 1:22 pm
YQR
-
ORD
6h 37m
1 stop
$374Air Canada
Fri, Jun 19 - Sun, Jun 21
Multiple Airlines Logo
7:05 pm - 6:21 pm
ORD
-
YQR
24h 16m
1 stop
Multiple Airlines Logo
9:05 pm - 5:00 pm
YQR
-
ORD
18h 55m
2 stops
$385Multiple Airlines
Mon, Apr 20 - Mon, Apr 27
Multiple Airlines Logo
5:11 am - 5:20 pm
ORD
-
YQR
13h 09m
2 stops
Multiple Airlines Logo
7:00 am - 4:40 pm
YQR
-
ORD
8h 40m
1 stop
$391Multiple Airlines
Mon, May 11 - Mon, May 18
WestJet Logo
5:30 pm - 10:50 am
ORD
-
YQR
18h 20m
1 stop
WestJet Logo
8:20 pm - 4:40 pm
YQR
-
ORD
43h 20m
2 stops
$402WestJet
Sun, Apr 26 - Tue, May 5

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
Apr 29
ORD6:40 pmChicago O'Hare Intl
15h 52m
1 stop
YQR9:32 amRegina
May 2
YQR5:45 amRegina
8h 10m
1 stop
ORD2:55 pmChicago O'Hare Intl
$342
Air Canada
Apr 29
ORD6:40 pmChicago O'Hare Intl
15h 52m
1 stop
YQR9:32 amRegina
May 2
YQR5:45 amRegina
13h 23m
2 stops
ORD8:08 pmChicago O'Hare Intl
$350
Air Canada
Apr 29
ORD6:40 pmChicago O'Hare Intl
15h 52m
1 stop
YQR9:32 amRegina
May 2
YQR5:45 amRegina
6h 40m
1 stop
ORD1:25 pmChicago O'Hare Intl
$353

WestJet flights from Chicago to Regina

Our best WestJet deals on Chicago to Regina flight tickets
WestJet
Apr 26
ORD5:30 pmChicago O'Hare Intl
18h 20m
1 stop
YQR10:50 amRegina
May 5
YQR8:20 pmRegina
43h 20m
2 stops
ORD4:40 pmChicago O'Hare Intl
$402
WestJet
Jun 12
ORD5:30 pmChicago O'Hare Intl
6h 50m
1 stop
YQR11:20 pmRegina
Jun 15
YQR6:00 amRegina
26h 24m
2 stops
ORD9:24 amChicago O'Hare Intl
$443
WestJet
Apr 24
ORD2:20 pmChicago O'Hare Intl
21h 24m
1 stop
YQR10:44 amRegina
May 1
YQR8:20 pmRegina
43h 20m
2 stops
ORD4:40 pmChicago O'Hare Intl
$448

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 March 10, 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

Cheapest round-trip

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 4/29

6:40 pm-9:32 am

1 stop15h 52m

Regina

Sat 5/2

5:45 am-2:55 pm

1 stop8h 10m

$342

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 4/29

6:40 pm-9:32 am

1 stop15h 52m

Regina

Sat 5/2

5:45 am-8:08 pm

2 stops13h 23m

$350

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 4/29

6:40 pm-9:32 am

1 stop15h 52m

Regina

Sat 5/2

5:45 am-1:25 pm

1 stop6h 40m

$353

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 4/23

7:13 pm-6:21 pm

1 stop24h 08m

Regina

Thu 4/30

7:00 am-4:40 pm

1 stop8h 40m

$356

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 4/29

6:40 pm-9:32 am

1 stop15h 52m

Regina

Sat 5/2

5:45 am-8:08 pm

2 stops13h 23m

$361

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 4/20

7:05 pm-6:21 pm

1 stop24h 16m

Regina

Mon 4/27

8:35 am-4:40 pm

1 stop7h 05m

$363
Quickest round-trip

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

8:40 pm-9:05 am

1 stop13h 25m

Regina

Sun 6/21

5:45 am-1:22 pm

1 stop6h 37m

$374

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 4/20

7:05 pm-6:21 pm

1 stop24h 16m

Regina

Mon 4/27

9:05 pm-5:00 pm

2 stops18h 55m

$385

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 5/11

5:11 am-5:20 pm

2 stops13h 09m

Regina

Mon 5/18

7:00 am-4:40 pm

1 stop8h 40m

$391

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sun 4/26

5:30 pm-10:50 am

1 stop18h 20m

Regina

Tue 5/5

8:20 pm-4:40 pm

2 stops43h 20m

$402

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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?

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

What airlines fly to Regina?

United Airlines, WestJet and Delta are the top three most popular airlines that fly to Regina from Chicago according to our data. United Airlines is the first choice among our users, with 44% 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.

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

7h 08m

Direct flights

None
The fastest flight from Chicago to Regina takes 7h 08m
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 7h 08m 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.

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
DeltaPriceFrom $137Free CancellationRating
7.9
8,277 reviews
Search Delta flights
United AirlinesPriceFrom $284Free CancellationRating
7.4
9,412 reviews
Search United Airlines flights
WestJetPriceFrom $328Free CancellationRating
7.2
3,288 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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