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Cheap flights from Chicago to Regina from $239

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Regina departing on 5/27. 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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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
5:30 pm - 1:10 am
ORD
-
YQR
8h 40m
1 stop
WestJet Logo
7:00 am - 4:40 pm
YQR
-
ORD
8h 40m
1 stop
$239WestJet
Wed, May 27 - Sat, May 30
WestJet Logo
5:30 pm - 11:15 am
ORD
-
YQR
18h 45m
2 stops
WestJet Logo
7:00 am - 4:40 pm
YQR
-
ORD
8h 40m
1 stop
$264WestJet
Wed, May 27 - Sat, May 30
WestJet Logo
5:30 pm - 11:15 am
ORD
-
YQR
18h 45m
2 stops
WestJet Logo
8:20 pm - 4:40 pm
YQR
-
ORD
19h 20m
2 stops
$288WestJet
Wed, May 27 - Sat, May 30
WestJet Logo
5:30 pm - 1:07 am
ORD
-
YQR
8h 37m
1 stop
WestJet Logo
11:45 am - 4:43 pm
YQR
-
ORD
27h 58m
1 stop
$362WestJet
Wed, Jun 24 - Mon, Jun 29
United Airlines Logo
7:00 am - 9:51 pm
ORD
-
YQR
15h 51m
1 stop
United Airlines Logo
9:45 am - 12:30 am
YQR
-
ORD
13h 45m
1 stop
$369United Airlines
Tue, Mar 24 - Tue, Mar 31
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
$371WestJet
Fri, Jun 19 - Sun, Jun 21
WestJet Logo
5:30 pm - 1:07 am
ORD
-
YQR
8h 37m
1 stop
WestJet Logo
10:05 am - 4:43 pm
YQR
-
ORD
29h 38m
2 stops
$382WestJet
Wed, Jun 24 - Mon, Jun 29
WestJet Logo
5:30 pm - 11:20 pm
ORD
-
YQR
6h 50m
1 stop
WestJet Logo
9:00 pm - 4:43 pm
YQR
-
ORD
18h 43m
1 stop
$383WestJet
Fri, Jun 19 - Sun, Jun 21
WestJet Logo
5:30 pm - 9:30 am
ORD
-
YQR
17h 00m
2 stops
WestJet Logo
5:30 pm - 4:43 pm
YQR
-
ORD
22h 13m
2 stops
$394WestJet
Wed, Jun 24 - Mon, Jun 29
WestJet Logo
5:30 pm - 11:20 pm
ORD
-
YQR
6h 50m
1 stop
WestJet Logo
9:00 pm - 4:43 pm
YQR
-
ORD
18h 43m
1 stop
$418WestJet
Fri, Jun 19 - Sun, Jun 21

WestJet flights from Chicago to Regina

Our best WestJet deals on Chicago to Regina flight tickets
WestJet
May 27
ORD5:30 pmChicago O'Hare Intl
8h 40m
1 stop
YQR1:10 amRegina
May 30
YQR7:00 amRegina
8h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
$239
WestJet
May 27
ORD5:30 pmChicago O'Hare Intl
18h 45m
2 stops
YQR11:15 amRegina
May 30
YQR7:00 amRegina
8h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
$264
WestJet
May 27
ORD5:30 pmChicago O'Hare Intl
18h 45m
2 stops
YQR11:15 amRegina
May 30
YQR8:20 pmRegina
19h 20m
2 stops
ORD4:40 pmChicago O'Hare Intl
$288

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
Mar 2
ORD8:40 pmChicago O'Hare Intl
13h 59m
1 stop
YQR10:39 amRegina
Mar 4
YQR5:00 amRegina
8h 01m
1 stop
ORD1:01 pmChicago O'Hare Intl
$532
Air Canada
Apr 9
ORD5:57 pmChicago O'Hare Intl
16h 35m
1 stop
YQR9:32 amRegina
Apr 13
YQR5:00 amRegina
8h 01m
1 stop
ORD2:01 pmChicago O'Hare Intl
$572
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
$573

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 9, 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

Wed 5/27

5:30 pm-1:10 am

1 stop8h 40m

Regina

Sat 5/30

7:00 am-4:40 pm

1 stop8h 40m

$239

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 5/27

5:30 pm-11:15 am

2 stops18h 45m

Regina

Sat 5/30

7:00 am-4:40 pm

1 stop8h 40m

$264

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 5/27

5:30 pm-11:15 am

2 stops18h 45m

Regina

Sat 5/30

8:20 pm-4:40 pm

2 stops19h 20m

$288

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 6/24

5:30 pm-1:07 am

1 stop8h 37m

Regina

Mon 6/29

11:45 am-4:43 pm

1 stop27h 58m

$362

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 3/24

7:00 am-9:51 pm

1 stop15h 51m

Regina

Tue 3/31

9:45 am-12:30 am

1 stop13h 45m

$369

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

$371

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 6/24

5:30 pm-1:07 am

1 stop8h 37m

Regina

Mon 6/29

10:05 am-4:43 pm

2 stops29h 38m

$382

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

5:30 pm-11:20 pm

1 stop6h 50m

Regina

Sun 6/21

9:00 pm-4:43 pm

1 stop18h 43m

$383

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 6/24

5:30 pm-9:30 am

2 stops17h 00m

Regina

Mon 6/29

5:30 pm-4:43 pm

2 stops22h 13m

$394

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

5:30 pm-11:20 pm

1 stop6h 50m

Regina

Sun 6/21

9:00 pm-4:43 pm

1 stop18h 43m

$418

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 02m

Direct flights

None
The fastest flight from Chicago to Regina takes 7h 02m
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 02m 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
9,259 reviews
Search United Airlines flights
WestJetPriceFrom $328Free CancellationRating
7.2
3,256 reviews
Search WestJet flights

  • How do I get Price Alerts for flights from Chicago to Regina?

    Confirm your travel details to search for the latest offers for flights from Chicago to Regina. While browsing offers there will be the option to toggle “Price Alerts”. You’ll then receive updates when prices for the flight route increase or decrease.

  • How can I save money on flights from Chicago to Regina with momondo?

    Plan your trips smart with the “Price Forecast” feature, which uses flight data to help you pick the best days to fly for the lowest fares. Our “Price Calendar” helps you get the most for your money by showing you when it’s most advantageous to fly. Curate your own travel experiences for less with “Explore”. Expert travel hacks to fuel your next adventure are a click away with “Discover” by momondo. Set up our “Price Alerts” to track fare changes and book when prices are at their lowest point.

  • How does momondo find its flight prices?

    We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

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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