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Cheap flights from Chicago to Regina from $122

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 5/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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 - 11:20 pm
ORD
-
YQR
6h 50m
1 stop
WestJet Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
$282WestJet
Mon, Apr 27 - Sun, May 3
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
$283WestJet
Fri, May 1 - Thu, May 7
Air Canada Logo
4:15 pm - 10:17 pm
ORD
-
YQR
7h 02m
1 stop
Air Canada Logo
5:00 am - 1:05 pm
YQR
-
ORD
7h 05m
1 stop
$295Air Canada
Fri, Apr 17 - Thu, Apr 23
United Airlines Logo
2:35 pm - 9:30 pm
ORD
-
YQR
7h 55m
1 stop
United Airlines Logo
9:45 am - 10:54 pm
YQR
-
ORD
12h 09m
1 stop
$296United Airlines
Wed, Apr 15 - Mon, Apr 20
United Airlines Logo
12:55 pm - 9:30 pm
ORD
-
YQR
9h 35m
1 stop
United Airlines Logo
9:45 am - 5:04 pm
YQR
-
ORD
6h 19m
1 stop
$297United Airlines
Tue, Apr 28 - Sat, May 2
United Airlines Logo
2:20 pm - 9:30 pm
ORD
-
YQR
8h 10m
1 stop
United Airlines Logo
9:45 am - 10:58 pm
YQR
-
ORD
12h 13m
1 stop
$298United Airlines
Wed, May 6 - Mon, May 11
Air Canada Logo
8:45 am - 7:07 pm
ORD
-
YQR
11h 22m
2 stops
Air Canada Logo
5:45 am - 2:55 pm
YQR
-
ORD
8h 10m
1 stop
$304Air Canada
Sat, May 9 - Fri, May 15
WestJet Logo
2:20 pm - 11:16 pm
ORD
-
YQR
9h 56m
1 stop
WestJet Logo
7:00 am - 4:40 pm
YQR
-
ORD
8h 40m
1 stop
$312WestJet
Fri, Apr 24 - Thu, Apr 30
WestJet Logo
5:30 pm - 9:45 am
ORD
-
YQR
17h 15m
1 stop
WestJet Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
$313WestJet
Sun, Apr 26 - Sun, May 3
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
$314WestJet
Fri, May 1 - Wed, May 6

WestJet flights from Chicago to Regina

Our best WestJet deals on Chicago to Regina flight tickets
WestJet
Aug 6
ORD5:30 pmChicago O'Hare Intl
8h 40m
1 stop
YQR1:10 amRegina
Aug 20
YQR8:35 amRegina
7h 05m
1 stop
ORD4:40 pmChicago O'Hare Intl
$249
WestJet
Apr 27
ORD5:30 pmChicago O'Hare Intl
6h 50m
1 stop
YQR11:20 pmRegina
May 3
YQR8:35 amRegina
7h 05m
1 stop
ORD4:40 pmChicago O'Hare Intl
$282
WestJet
May 1
ORD5:30 pmChicago O'Hare Intl
8h 40m
1 stop
YQR1:10 amRegina
May 7
YQR8:35 amRegina
7h 05m
1 stop
ORD4:40 pmChicago O'Hare Intl
$283

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
Apr 17
ORD4:15 pmChicago O'Hare Intl
7h 02m
1 stop
YQR10:17 pmRegina
Apr 23
YQR5:00 amRegina
7h 05m
1 stop
ORD1:05 pmChicago O'Hare Intl
$295
Air Canada
May 9
ORD8:45 amChicago O'Hare Intl
11h 22m
2 stops
YQR7:07 pmRegina
May 15
YQR5:45 amRegina
8h 10m
1 stop
ORD2:55 pmChicago O'Hare Intl
$304
Air Canada
May 1
ORD9:55 amChicago O'Hare Intl
10h 12m
1 stop
YQR7:07 pmRegina
May 5
YQR5:45 amRegina
6h 40m
1 stop
ORD1:25 pmChicago O'Hare Intl
$320

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 1, 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

Mon 4/27

5:30 pm-11:20 pm

1 stop6h 50m

Regina

Sun 5/3

8:35 am-4:40 pm

1 stop7h 05m

$282

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 5/1

5:30 pm-1:10 am

1 stop8h 40m

Regina

Thu 5/7

8:35 am-4:40 pm

1 stop7h 05m

$283

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 4/17

4:15 pm-10:17 pm

1 stop7h 02m

Regina

Thu 4/23

5:00 am-1:05 pm

1 stop7h 05m

$295

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 4/15

2:35 pm-9:30 pm

1 stop7h 55m

Regina

Mon 4/20

9:45 am-10:54 pm

1 stop12h 09m

$296

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 4/28

12:55 pm-9:30 pm

1 stop9h 35m

Regina

Sat 5/2

9:45 am-5:04 pm

1 stop6h 19m

$297

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 5/6

2:20 pm-9:30 pm

1 stop8h 10m

Regina

Mon 5/11

9:45 am-10:58 pm

1 stop12h 13m

$298

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 5/9

8:45 am-7:07 pm

2 stops11h 22m

Regina

Fri 5/15

5:45 am-2:55 pm

1 stop8h 10m

$304

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 4/24

2:20 pm-11:16 pm

1 stop9h 56m

Regina

Thu 4/30

7:00 am-4:40 pm

1 stop8h 40m

$312

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sun 4/26

5:30 pm-9:45 am

1 stop17h 15m

Regina

Sun 5/3

8:35 am-4:40 pm

1 stop7h 05m

$313

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 5/1

5:30 pm-1:10 am

1 stop8h 40m

Regina

Wed 5/6

9:05 pm-4:40 pm

1 stop18h 35m

$314

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?

United Airlines 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 41% 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

14h 12m

Direct flights

None
The fastest flight from Chicago to Regina takes 14h 12m
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 14h 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.

  • 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
DeltaPriceFrom $137Free CancellationRating
7.9
8,246 reviews
Search Delta flights
United AirlinesPriceFrom $284Free CancellationRating
7.4
9,365 reviews
Search United Airlines flights
WestJetPriceFrom $328Free CancellationRating
7.2
3,276 reviews
Search WestJet flights

Traveling to a place near Regina?

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