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Cheap flights from Chicago to Regina from $335

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 4/7. 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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Cheap round-trip flights

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United Airlines Logo
12:45 pm - 9:51 pmORD-YQR
10h 06m1 stop
United Airlines Logo
9:45 am - 10:40 pmYQR-ORD
11h 55m1 stop
$335United Airlines
Find Deal
Tue, Apr 7 - Wed, Apr 8
Multiple Airlines Logo
10:27 am - 5:39 pmORD-YQR
31h 12m3 stops
Multiple Airlines Logo
9:45 pm - 5:14 pmYQR-ORD
19h 29m3 stops
$476Multiple Airlines
Find Deal
Sat, Jan 10 - Sun, Jan 11
Multiple Airlines Logo
3:55 pm - 11:19 pmORD-YQR
7h 24m1 stop
Multiple Airlines Logo
1:40 pm - 10:05 pmYQR-ORD
8h 25m1 stop
$500Multiple Airlines
Find Deal
Sat, Jan 10 - Sun, Jan 11
Multiple Airlines Logo
2:15 pm - 10:51 pmORD-YQR
8h 36m1 stop
Multiple Airlines Logo
5:00 am - 6:51 pmYQR-ORD
13h 51m2 stops
$514Multiple Airlines
Find Deal
Sat, Jan 10 - Sun, Jan 11
Multiple Airlines Logo
5:15 am - 12:23 amORD-YQR
19h 08m3 stops
Multiple Airlines Logo
7:00 am - 5:14 pmYQR-ORD
34h 14m2 stops
$519Multiple Airlines
Find Deal
Sat, Jan 10 - Sun, Jan 11
Air Canada Logo
3:00 pm - 10:13 pmORD-YQR
8h 13m1 stop
Air Canada Logo
5:00 am - 7:50 pmYQR-ORD
13h 50m2 stops
$534Air Canada
Find Deal
Tue, Apr 7 - Wed, Apr 8
Multiple Airlines Logo
10:27 am - 5:39 pmORD-YQR
31h 12m3 stops
Multiple Airlines Logo
9:45 pm - 1:35 pmYQR-ORD
15h 50m1 stop
$553Multiple Airlines
Find Deal
Sat, Jan 10 - Sun, Jan 11
United Airlines Logo
2:25 pm - 9:51 pmORD-YQR
8h 26m2 stops
United Airlines Logo
5:00 am - 2:01 pmYQR-ORD
8h 01m1 stop
$571United Airlines
Find Deal
Tue, Apr 7 - Wed, Apr 8
Air Canada Logo
12:59 pm - 10:13 pmORD-YQR
10h 14m2 stops
Air Canada Logo
5:00 am - 7:50 pmYQR-ORD
13h 50m2 stops
$659Air Canada
Find Deal
Tue, Apr 7 - Wed, Apr 8
Air Canada Logo
12:59 pm - 10:13 pmORD-YQR
10h 14m2 stops
Air Canada Logo
5:00 am - 7:50 pmYQR-ORD
13h 50m2 stops
$729Air Canada
Find Deal
Tue, Apr 7 - Wed, Apr 8

United Airlines flights from Chicago to Regina

Our best United Airlines deals on Chicago to Regina flight tickets
United Airlines
Apr 7
ORD12:45 pmChicago O'Hare Intl
10h 06m
1 stop
YQR9:51 pmRegina
Apr 8
YQR9:45 amRegina
11h 55m
1 stop
ORD10:40 pmChicago O'Hare Intl
$335
Find similar
United Airlines
Apr 7
ORD2:25 pmChicago O'Hare Intl
8h 26m
2 stops
YQR9:51 pmRegina
Apr 8
YQR5:00 amRegina
8h 01m
1 stop
ORD2:01 pmChicago O'Hare Intl
$571
Find similar

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
Apr 7
ORD3:00 pmChicago O'Hare Intl
8h 13m
1 stop
YQR10:13 pmRegina
Apr 8
YQR5:00 amRegina
13h 50m
2 stops
ORD7:50 pmChicago O'Hare Intl
$534
Find similar
Air Canada
Apr 7
ORD12:59 pmChicago O'Hare Intl
10h 14m
2 stops
YQR10:13 pmRegina
Apr 8
YQR5:00 amRegina
13h 50m
2 stops
ORD7:50 pmChicago O'Hare Intl
$659
Find similar
Air Canada
Apr 7
ORD12:59 pmChicago O'Hare Intl
10h 14m
2 stops
YQR10:13 pmRegina
Apr 8
YQR5:00 amRegina
13h 50m
2 stops
ORD7:50 pmChicago O'Hare Intl
$729
Find similar

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 November 10, 2025.
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

Tue 4/7

12:45 pm-9:51 pm

1 stop10h 06m

Regina

Wed 4/8

9:45 am-10:40 pm

1 stop11h 55m

$335

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 1/10

10:27 am-5:39 pm

3 stops31h 12m

Regina

Sun 1/11

9:45 pm-5:14 pm

3 stops19h 29m

$476

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 1/10

3:55 pm-11:19 pm

1 stop7h 24m

Regina

Sun 1/11

1:40 pm-10:05 pm

1 stop8h 25m

$500

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 1/10

2:15 pm-10:51 pm

1 stop8h 36m

Regina

Sun 1/11

5:00 am-6:51 pm

2 stops13h 51m

$514

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 1/10

5:15 am-12:23 am

3 stops19h 08m

Regina

Sun 1/11

7:00 am-5:14 pm

2 stops34h 14m

$519

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 4/7

3:00 pm-10:13 pm

1 stop8h 13m

Regina

Wed 4/8

5:00 am-7:50 pm

2 stops13h 50m

$534

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 1/10

10:27 am-5:39 pm

3 stops31h 12m

Regina

Sun 1/11

9:45 pm-1:35 pm

1 stop15h 50m

$553

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 4/7

2:25 pm-9:51 pm

2 stops8h 26m

Regina

Wed 4/8

5:00 am-2:01 pm

1 stop8h 01m

$571

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 4/7

12:59 pm-10:13 pm

2 stops10h 14m

Regina

Wed 4/8

5:00 am-7:50 pm

2 stops13h 50m

$659

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 4/7

12:59 pm-10:13 pm

2 stops10h 14m

Regina

Wed 4/8

5:00 am-7:50 pm

2 stops13h 50m

$729

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 day to depart on your flight to Regina?

The cheapest day to depart from Chicago to Regina is on a Wednesday when prices can be found for as low as $348. Flights from Chicago to Regina on a Sunday will generally be more expensive and average around $1,034. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Regina?

The cheapest time of day to fly to Regina is in the afternoon when flights can be purchased for as low as $283. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $576 on average. Flights to Regina from Chicago in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

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

Direct flights

None
There are no direct flights from Chicago to Regina. There are no popular flight routes from Chicago to Regina.
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  • 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 24m 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
9,011 reviews
Search United Airlines flights
WestJetPriceFrom $328Free CancellationRating
7.2
3,156 reviews
Search WestJet flights

Traveling to a place near Regina?

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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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