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Cheap flights from Chicago to Regina from $98

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 2/2. 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
2:20 pm - 10:32 am
ORD
-
YQR
20h 12m
2 stops
WestJet Logo
6:10 pm - 1:35 pm
YQR
-
ORD
19h 25m
2 stops
$222WestJet
Mon, Feb 2 - Thu, Feb 5
WestJet Logo
2:20 pm - 10:32 am
ORD
-
YQR
20h 12m
2 stops
WestJet Logo
2:10 pm - 1:35 pm
YQR
-
ORD
23h 25m
1 stop
$233WestJet
Mon, Feb 2 - Thu, Feb 5
WestJet Logo
2:20 pm - 11:44 am
ORD
-
YQR
21h 24m
1 stop
WestJet Logo
9:45 pm - 1:35 pm
YQR
-
ORD
15h 50m
1 stop
$243WestJet
Mon, Feb 2 - Thu, Feb 5
United Airlines Logo
1:55 pm - 10:51 pm
ORD
-
YQR
8h 56m
1 stop
United Airlines Logo
10:45 am - 7:51 pm
YQR
-
ORD
9h 06m
1 stop
$244United Airlines
Mon, Feb 2 - Fri, Feb 6
WestJet Logo
2:20 pm - 10:32 am
ORD
-
YQR
20h 12m
2 stops
WestJet Logo
6:10 am - 1:35 pm
YQR
-
ORD
7h 25m
1 stop
$254WestJet
Mon, Feb 2 - Fri, Feb 6
WestJet Logo
5:30 pm - 11:02 pm
ORD
-
YQR
6h 32m
1 stop
WestJet Logo
5:30 pm - 4:43 pm
YQR
-
ORD
46h 13m
2 stops
$307WestJet
Fri, Jun 19 - Sun, Jun 21
Air Canada Logo
8:40 pm - 9:20 am
ORD
-
YQR
13h 40m
1 stop
Air Canada Logo
8:10 pm - 9:00 am
YQR
-
ORD
11h 50m
1 stop
$315Air Canada
Fri, Jun 19 - Sun, Jun 21
Air Canada Logo
9:50 am - 7:10 pm
ORD
-
YQR
10h 20m
1 stop
Air Canada Logo
8:10 pm - 9:00 am
YQR
-
ORD
11h 50m
1 stop
$316Air Canada
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
46h 13m
2 stops
$323WestJet
Fri, Jun 19 - Sun, Jun 21
Multiple Airlines Logo
5:15 am - 1:15 am
ORD
-
YQR
20h 00m
2 stops
Multiple Airlines Logo
6:10 am - 1:35 pm
YQR
-
ORD
7h 25m
1 stop
$324Multiple Airlines
Wed, Mar 4 - Fri, Mar 6

WestJet flights from Chicago to Regina

Our best WestJet deals on Chicago to Regina flight tickets
WestJet
Feb 2
ORD2:20 pmChicago O'Hare Intl
20h 12m
2 stops
YQR10:32 amRegina
Feb 5
YQR6:10 pmRegina
19h 25m
2 stops
ORD1:35 pmChicago O'Hare Intl
$222
WestJet
Feb 2
ORD2:20 pmChicago O'Hare Intl
20h 12m
2 stops
YQR10:32 amRegina
Feb 5
YQR2:10 pmRegina
23h 25m
1 stop
ORD1:35 pmChicago O'Hare Intl
$233
WestJet
Feb 2
ORD2:20 pmChicago O'Hare Intl
21h 24m
1 stop
YQR11:44 amRegina
Feb 5
YQR9:45 pmRegina
15h 50m
1 stop
ORD1:35 pmChicago O'Hare Intl
$243

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
Jun 19
ORD8:40 pmChicago O'Hare Intl
13h 40m
1 stop
YQR9:20 amRegina
Jun 21
YQR8:10 pmRegina
11h 50m
1 stop
ORD9:00 amChicago O'Hare Intl
$315
Air Canada
Jun 19
ORD9:50 amChicago O'Hare Intl
10h 20m
1 stop
YQR7:10 pmRegina
Jun 21
YQR8:10 pmRegina
11h 50m
1 stop
ORD9:00 amChicago O'Hare Intl
$316
Air Canada
Feb 26
ORD6:28 pmChicago O'Hare Intl
16h 11m
1 stop
YQR10:39 amRegina
Mar 5
YQR5:00 amRegina
8h 01m
1 stop
ORD1:01 pmChicago O'Hare Intl
$356

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 January 14, 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 2/2

2:20 pm-10:32 am

2 stops20h 12m

Regina

Thu 2/5

6:10 pm-1:35 pm

2 stops19h 25m

$222

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 2/2

2:20 pm-10:32 am

2 stops20h 12m

Regina

Thu 2/5

2:10 pm-1:35 pm

1 stop23h 25m

$233

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 2/2

2:20 pm-11:44 am

1 stop21h 24m

Regina

Thu 2/5

9:45 pm-1:35 pm

1 stop15h 50m

$243

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 2/2

1:55 pm-10:51 pm

1 stop8h 56m

Regina

Fri 2/6

10:45 am-7:51 pm

1 stop9h 06m

$244

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 2/2

2:20 pm-10:32 am

2 stops20h 12m

Regina

Fri 2/6

6:10 am-1:35 pm

1 stop7h 25m

$254

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

5:30 pm-11:02 pm

1 stop6h 32m

Regina

Sun 6/21

5:30 pm-4:43 pm

2 stops46h 13m

$307

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

8:40 pm-9:20 am

1 stop13h 40m

Regina

Sun 6/21

8:10 pm-9:00 am

1 stop11h 50m

$315

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

9:50 am-7:10 pm

1 stop10h 20m

Regina

Sun 6/21

8:10 pm-9:00 am

1 stop11h 50m

$316

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

5:30 pm-9:30 am

2 stops17h 00m

Regina

Sun 6/21

5:30 pm-4:43 pm

2 stops46h 13m

$323

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 3/4

5:15 am-1:15 am

2 stops20h 00m

Regina

Fri 3/6

6:10 am-1:35 pm

1 stop7h 25m

$324

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, WestJet, and Air Canada 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 15m

Direct flights

None
The fastest flight from Chicago to Regina takes 8h 15m
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 15m 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
9,152 reviews
Search United Airlines flights
WestJetPriceFrom $328Free CancellationRating
7.2
3,238 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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