Cheap flights from Chicago to Regina from $95

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 9/17. 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 (CHI-YQR)

Cheap round-trip flights

WestJet Logo
5:30 pm - 1:17 amORD-YQR
8h 47m1 stop
WestJet Logo
5:10 am - 1:35 pmYQR-ORD
7h 25m1 stop
$198WestJet
Find Deal
Thu, Oct 23 - Sun, Oct 26
 Logo
10:53 am - 9:36 pmORD-YQR
11h 43m1 stop
 Logo
5:00 am - 1:01 pmYQR-ORD
7h 01m1 stop
Wed, Oct 22 - Wed, Oct 29
WestJet Logo
5:30 pm - 5:01 pmORD-YQR
24h 31m2 stops
WestJet Logo
5:10 am - 1:35 pmYQR-ORD
7h 25m1 stop
$238WestJet
Find Deal
Thu, Oct 23 - Sun, Oct 26
United Airlines Logo
1:55 pm - 10:51 pmORD-YQR
8h 56m1 stop
United Airlines Logo
10:45 am - 4:58 pmYQR-ORD
6h 13m1 stop
$239United Airlines
Find Deal
Thu, Nov 6 - Tue, Nov 11
 Logo
2:53 pm - 9:36 pmORD-YQR
7h 43m1 stop
 Logo
5:00 am - 8:00 pmYQR-ORD
14h 00m2 stops
Wed, Oct 22 - Wed, Oct 29
WestJet Logo
5:30 pm - 5:01 pmORD-YQR
24h 31m2 stops
WestJet Logo
5:10 pm - 1:35 pmYQR-ORD
19h 25m2 stops
$258WestJet
Find Deal
Thu, Oct 23 - Sun, Oct 26
Air Canada Logo
8:15 pm - 10:39 amORD-YQR
14h 24m1 stop
Air Canada Logo
5:00 am - 8:00 pmYQR-ORD
15h 00m2 stops
$266Air Canada
Find Deal
Thu, Nov 6 - Tue, Nov 11
Air Canada Logo
12:50 pm - 10:39 amORD-YQR
21h 49m2 stops
Air Canada Logo
5:00 am - 8:00 pmYQR-ORD
15h 00m2 stops
$305Air Canada
Find Deal
Thu, Nov 6 - Tue, Nov 11
 Logo
5:30 pm - 8:05 amORD-YQR
15h 35m1 stop
 Logo
10:15 am - 11:53 pmYQR-ORD
36h 38m2 stops
Mon, Sep 29 - Mon, Oct 6
Delta Logo
7:10 am - 4:41 pmORD-YQR
10h 31m2 stops
Delta Logo
11:45 am - 11:58 pmYQR-ORD
11h 13m2 stops
$366Delta
Find Deal
Wed, Oct 22 - Wed, Oct 29

WestJet flights from Chicago to Regina

Our best WestJet deals on Chicago to Regina flight tickets
WestJet
Oct 23
ORD5:30 pmChicago O'Hare Intl
8h 47m
1 stop
YQR1:17 amRegina
Oct 26
YQR5:10 amRegina
7h 25m
1 stop
ORD1:35 pmChicago O'Hare Intl
WestJet
Oct 23
ORD5:30 pmChicago O'Hare Intl
24h 31m
2 stops
YQR5:01 pmRegina
Oct 26
YQR5:10 amRegina
7h 25m
1 stop
ORD1:35 pmChicago O'Hare Intl
WestJet
Oct 23
ORD5:30 pmChicago O'Hare Intl
24h 31m
2 stops
YQR5:01 pmRegina
Oct 26
YQR5:10 pmRegina
19h 25m
2 stops
ORD1:35 pmChicago O'Hare Intl

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
Nov 6
ORD8:15 pmChicago O'Hare Intl
14h 24m
1 stop
YQR10:39 amRegina
Nov 11
YQR5:00 amRegina
15h 00m
2 stops
ORD8:00 pmChicago O'Hare Intl
Air Canada
Nov 6
ORD12:50 pmChicago O'Hare Intl
21h 49m
2 stops
YQR10:39 amRegina
Nov 11
YQR5:00 amRegina
15h 00m
2 stops
ORD8:00 pmChicago O'Hare Intl
Air Canada
Sep 12
ORD3:45 pmChicago O'Hare Intl
9h 41m
1 stop
YQR12:26 amRegina
Sep 15
YQR7:15 pmRegina
15h 48m
1 stop
ORD12:03 pmChicago O'Hare Intl

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 September 2, 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

Thu 10/23

5:30 pm-1:17 am

1 stop8h 47m

Regina

Sun 10/26

5:10 am-1:35 pm

1 stop7h 25m

$198

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 10/22

10:53 am-9:36 pm

1 stop11h 43m

Regina

Wed 10/29

5:00 am-1:01 pm

1 stop7h 01m

$235

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 10/23

5:30 pm-5:01 pm

2 stops24h 31m

Regina

Sun 10/26

5:10 am-1:35 pm

1 stop7h 25m

$238

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 11/6

1:55 pm-10:51 pm

1 stop8h 56m

Regina

Tue 11/11

10:45 am-4:58 pm

1 stop6h 13m

$239

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 10/22

2:53 pm-9:36 pm

1 stop7h 43m

Regina

Wed 10/29

5:00 am-8:00 pm

2 stops14h 00m

$240

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 10/23

5:30 pm-5:01 pm

2 stops24h 31m

Regina

Sun 10/26

5:10 pm-1:35 pm

2 stops19h 25m

$258

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 11/6

8:15 pm-10:39 am

1 stop14h 24m

Regina

Tue 11/11

5:00 am-8:00 pm

2 stops15h 00m

$266

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 11/6

12:50 pm-10:39 am

2 stops21h 49m

Regina

Tue 11/11

5:00 am-8:00 pm

2 stops15h 00m

$305

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 9/29

5:30 pm-8:05 am

1 stop15h 35m

Regina

Mon 10/6

10:15 am-11:53 pm

2 stops36h 38m

$306

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 10/22

7:10 am-4:41 pm

2 stops10h 31m

Regina

Wed 10/29

11:45 am-11:58 pm

2 stops11h 13m

$366

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 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.
  • 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 31m 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
8,937 reviews
Search United Airlines flights
WestJetPriceFrom $330Free CancellationRating
7.2
3,082 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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1 adult
Sun 9/7
Sun 9/14

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