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Cheap flights from Chicago to Regina from $141

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 1/16. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
2:20 pm - 9:08 pmORD-YQR
6h 48m1 stop
Multiple Airlines Logo
5:00 am - 1:01 pmYQR-ORD
8h 01m1 stop
$268Multiple Airlines
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Mon, Jan 26 - Tue, Feb 3
WestJet Logo
2:20 pm - 12:23 amORD-YQR
10h 03m1 stop
WestJet Logo
6:10 am - 1:35 pmYQR-ORD
7h 25m1 stop
$286WestJet
Find Deal
Fri, Jan 16 - Fri, Jan 23
Multiple Airlines Logo
2:20 pm - 1:56 amORD-YQR
11h 36m1 stop
Multiple Airlines Logo
4:25 pm - 4:51 pmYQR-ORD
24h 26m2 stops
$333Multiple Airlines
Find Deal
Fri, Jan 16 - Fri, Jan 23
United Airlines Logo
12:53 pm - 10:51 pmORD-YQR
9h 58m1 stop
United Airlines Logo
10:45 am - 5:04 pmYQR-ORD
6h 19m1 stop
$335United Airlines
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Tue, Jan 20 - Tue, Jan 27
Multiple Airlines Logo
3:55 pm - 11:45 amORD-YQR
19h 50m2 stops
Multiple Airlines Logo
5:00 am - 1:01 pmYQR-ORD
8h 01m1 stop
$340Multiple Airlines
Find Deal
Mon, Jan 26 - Tue, Feb 3
Air Canada Logo
3:35 pm - 10:39 amORD-YQR
19h 04m2 stops
Air Canada Logo
5:00 am - 8:10 pmYQR-ORD
15h 10m2 stops
$369Air Canada
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Mon, Jan 26 - Tue, Feb 3
Multiple Airlines Logo
3:55 pm - 11:45 amORD-YQR
19h 50m2 stops
Multiple Airlines Logo
7:20 pm - 2:55 pmYQR-ORD
19h 35m3 stops
$370Multiple Airlines
Find Deal
Mon, Jan 26 - Tue, Feb 3
WestJet Logo
12:05 pm - 1:15 amORD-YQR
13h 10m2 stops
WestJet Logo
5:10 pm - 1:35 pmYQR-ORD
19h 25m2 stops
$392WestJet
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Thu, Mar 5 - Sun, Mar 8
United Airlines Logo
8:18 pm - 10:51 pmORD-YQR
26h 33m2 stops
United Airlines Logo
10:45 am - 7:45 amYQR-ORD
21h 00m2 stops
$406United Airlines
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Tue, Jan 20 - Tue, Jan 27
United Airlines Logo
10:40 am - 10:51 pmORD-YQR
12h 11m1 stop
United Airlines Logo
10:45 am - 7:45 amYQR-ORD
21h 00m2 stops
$411United Airlines
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Tue, Jan 20 - Tue, Jan 27

WestJet flights from Chicago to Regina

Our best WestJet deals on Chicago to Regina flight tickets
WestJet
Jan 16
ORD2:20 pmChicago O'Hare Intl
10h 03m
1 stop
YQR12:23 amRegina
Jan 23
YQR6:10 amRegina
7h 25m
1 stop
ORD1:35 pmChicago O'Hare Intl
$286
Find similar
WestJet
Mar 5
ORD12:05 pmChicago O'Hare Intl
13h 10m
2 stops
YQR1:15 amRegina
Mar 8
YQR5:10 pmRegina
19h 25m
2 stops
ORD1:35 pmChicago O'Hare Intl
$392
Find similar
WestJet
Dec 8
ORD2:20 pmChicago O'Hare Intl
20h 14m
2 stops
YQR10:34 amRegina
Dec 12
YQR6:10 amRegina
7h 25m
1 stop
ORD1:35 pmChicago O'Hare Intl
$719
Find similar

United Airlines flights from Chicago to Regina

Our best United Airlines deals on Chicago to Regina flight tickets
United Airlines
Jan 20
ORD12:53 pmChicago O'Hare Intl
9h 58m
1 stop
YQR10:51 pmRegina
Jan 27
YQR10:45 amRegina
6h 19m
1 stop
ORD5:04 pmChicago O'Hare Intl
$335
Find similar
United Airlines
Jan 20
ORD8:18 pmChicago O'Hare Intl
26h 33m
2 stops
YQR10:51 pmRegina
Jan 27
YQR10:45 amRegina
21h 00m
2 stops
ORD7:45 amChicago O'Hare Intl
$406
Find similar
United Airlines
Jan 20
ORD10:40 amChicago O'Hare Intl
12h 11m
1 stop
YQR10:51 pmRegina
Jan 27
YQR10:45 amRegina
21h 00m
2 stops
ORD7:45 amChicago O'Hare Intl
$411
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 December 3, 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

Mon 1/26

2:20 pm-9:08 pm

1 stop6h 48m

Regina

Tue 2/3

5:00 am-1:01 pm

1 stop8h 01m

$268

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 1/16

2:20 pm-12:23 am

1 stop10h 03m

Regina

Fri 1/23

6:10 am-1:35 pm

1 stop7h 25m

$286

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 1/16

2:20 pm-1:56 am

1 stop11h 36m

Regina

Fri 1/23

4:25 pm-4:51 pm

2 stops24h 26m

$333

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 1/20

12:53 pm-10:51 pm

1 stop9h 58m

Regina

Tue 1/27

10:45 am-5:04 pm

1 stop6h 19m

$335

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 1/26

3:55 pm-11:45 am

2 stops19h 50m

Regina

Tue 2/3

5:00 am-1:01 pm

1 stop8h 01m

$340

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 1/26

3:35 pm-10:39 am

2 stops19h 04m

Regina

Tue 2/3

5:00 am-8:10 pm

2 stops15h 10m

$369

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 1/26

3:55 pm-11:45 am

2 stops19h 50m

Regina

Tue 2/3

7:20 pm-2:55 pm

3 stops19h 35m

$370

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 3/5

12:05 pm-1:15 am

2 stops13h 10m

Regina

Sun 3/8

5:10 pm-1:35 pm

2 stops19h 25m

$392

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 1/20

8:18 pm-10:51 pm

2 stops26h 33m

Regina

Tue 1/27

10:45 am-7:45 am

2 stops21h 00m

$406

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 1/20

10:40 am-10:51 pm

1 stop12h 11m

Regina

Tue 1/27

10:45 am-7:45 am

2 stops21h 00m

$411

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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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

Fastest flight time

6h 48m

Direct flights

None
The fastest flight from Chicago to Regina takes 6h 48m
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 6h 48m 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
9,064 reviews
Search United Airlines flights
WestJetPriceFrom $328Free CancellationRating
7.2
3,190 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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