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Cheap flights from Chicago to Regina from $181

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 4/24. 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
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
$312WestJet
søn., apr. 26 - søn., maj 3
WestJet Logo
5:30 pm - 11:20 pm
ORD
-
YQR
6h 50m
1 stop
WestJet Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
$313WestJet
tor., maj 14 - tor., maj 21
Multiple Airlines Logo
10:40 am - 7:45 pm
ORD
-
YQR
10h 05m
2 stops
Multiple Airlines Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
$357Multiple Airlines
tor., maj 14 - tor., maj 21
Multiple Airlines Logo
8:06 pm - 5:20 pm
ORD
-
YQR
22h 14m
1 stop
Multiple Airlines Logo
10:45 am - 5:24 pm
YQR
-
ORD
5h 39m
1 stop
$377Multiple Airlines
tor., maj 28 - tor., juni 4
United Airlines Logo
2:30 pm - 9:30 pm
ORD
-
YQR
8h 00m
1 stop
United Airlines Logo
9:45 am - 7:04 pm
YQR
-
ORD
8h 19m
1 stop
$378United Airlines
lør., apr. 18 - tir., maj 12
United Airlines Logo
6:00 am - 9:30 pm
ORD
-
YQR
16h 30m
1 stop
United Airlines Logo
9:45 am - 10:49 pm
YQR
-
ORD
12h 04m
1 stop
$383United Airlines
tir., juni 2 - fre., juni 5
United Airlines Logo
6:00 am - 9:30 pm
ORD
-
YQR
16h 30m
1 stop
United Airlines Logo
9:45 am - 11:19 pm
YQR
-
ORD
12h 34m
1 stop
$390United Airlines
tir., juni 2 - fre., juni 5
WestJet Logo
5:30 pm - 11:15 am
ORD
-
YQR
18h 45m
2 stops
WestJet Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
$399WestJet
søn., apr. 26 - søn., maj 3
Multiple Airlines Logo
9:37 pm - 5:20 pm
ORD
-
YQR
20h 43m
2 stops
Multiple Airlines Logo
6:00 am - 4:40 pm
YQR
-
ORD
9h 40m
1 stop
$406Multiple Airlines
lør., maj 16 - lør., maj 23
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
$409Air Canada
fre., juni 19 - søn., juni 21

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
8h 40m
1 stop
YQR1:10 amRegina
May 3
YQR8:35 amRegina
7h 05m
1 stop
ORD4:40 pmChicago O'Hare Intl
$312
WestJet
May 14
ORD5:30 pmChicago O'Hare Intl
6h 50m
1 stop
YQR11:20 pmRegina
May 21
YQR8:35 amRegina
7h 05m
1 stop
ORD4:40 pmChicago O'Hare Intl
$313
WestJet
Apr 26
ORD5:30 pmChicago O'Hare Intl
18h 45m
2 stops
YQR11:15 amRegina
May 3
YQR8:35 amRegina
7h 05m
1 stop
ORD4:40 pmChicago O'Hare Intl
$399

United Airlines flights from Chicago to Regina

Our best United Airlines deals on Chicago to Regina flight tickets
United Airlines
Apr 18
ORD2:30 pmChicago O'Hare Intl
8h 00m
1 stop
YQR9:30 pmRegina
May 12
YQR9:45 amRegina
8h 19m
1 stop
ORD7:04 pmChicago O'Hare Intl
$378
United Airlines
Jun 2
ORD6:00 amChicago O'Hare Intl
16h 30m
1 stop
YQR9:30 pmRegina
Jun 5
YQR9:45 amRegina
12h 04m
1 stop
ORD10:49 pmChicago O'Hare Intl
$383
United Airlines
Jun 2
ORD6:00 amChicago O'Hare Intl
16h 30m
1 stop
YQR9:30 pmRegina
Jun 5
YQR9:45 amRegina
12h 34m
1 stop
ORD11:19 pmChicago O'Hare Intl
$390

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 april 2, 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

søn. 4/26

5:30 pm-1:10 am

1 stop8h 40m

Regina

søn. 5/3

8:35 am-4:40 pm

1 stop7h 05m

$312
Quickest round-trip

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

tor. 5/14

5:30 pm-11:20 pm

1 stop6h 50m

Regina

tor. 5/21

8:35 am-4:40 pm

1 stop7h 05m

$313

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

tor. 5/14

10:40 am-7:45 pm

2 stops10h 05m

Regina

tor. 5/21

8:35 am-4:40 pm

1 stop7h 05m

$357

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

tor. 5/28

8:06 pm-5:20 pm

1 stop22h 14m

Regina

tor. 6/4

10:45 am-5:24 pm

1 stop5h 39m

$377

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

lør. 4/18

2:30 pm-9:30 pm

1 stop8h 00m

Regina

tir. 5/12

9:45 am-7:04 pm

1 stop8h 19m

$378

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

tir. 6/2

6:00 am-9:30 pm

1 stop16h 30m

Regina

fre. 6/5

9:45 am-10:49 pm

1 stop12h 04m

$383

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

tir. 6/2

6:00 am-9:30 pm

1 stop16h 30m

Regina

fre. 6/5

9:45 am-11:19 pm

1 stop12h 34m

$390

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

søn. 4/26

5:30 pm-11:15 am

2 stops18h 45m

Regina

søn. 5/3

8:35 am-4:40 pm

1 stop7h 05m

$399

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

lør. 5/16

9:37 pm-5:20 pm

2 stops20h 43m

Regina

lør. 5/23

6:00 am-4:40 pm

1 stop9h 40m

$406

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

fre. 6/19

8:40 pm-9:05 am

1 stop13h 25m

Regina

søn. 6/21

5:45 am-1:22 pm

1 stop6h 37m

$409

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?

Air Canada and Delta 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 40% 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 12m

Direct flights

None
The fastest flight from Chicago to Regina takes 7h 12m
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 12m 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
United AirlinesPriceFrom $86Free CancellationRating
7.4
9,535 reviews
Search United Airlines flights
DeltaPriceFrom $137Free CancellationRating
7.9
8,372 reviews
Search Delta flights
WestJetPriceFrom $330Free CancellationRating
7.2
3,310 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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