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Cheap flights from Chicago to Regina from $390

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 5/13. 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.
United Airlines Logo
3:00 pm - 9:30 pm
ORD
-
YQR
7h 30m
1 stop
United Airlines Logo
9:45 am - 12:58 am
YQR
-
ORD
14h 13m
1 stop
$390United Airlines
Wed, May 13 - Sun, May 17
United Airlines Logo
3:00 pm - 9:30 pm
ORD
-
YQR
7h 30m
1 stop
United Airlines Logo
9:45 am - 12:58 am
YQR
-
ORD
14h 13m
1 stop
$411United Airlines
Wed, May 13 - Sun, May 17
Air Canada Logo
8:40 pm - 9:05 am
ORD
-
YQR
13h 25m
1 stop
Air Canada Logo
5:45 am - 2:55 pm
YQR
-
ORD
8h 10m
1 stop
$416Air Canada
Thu, Jun 18 - Sun, Jun 21
Multiple Airlines Logo
9:37 pm - 5:20 pm
ORD
-
YQR
20h 43m
2 stops
Multiple Airlines Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
$418Multiple Airlines
Wed, May 20 - Wed, May 27
Multiple Airlines Logo
6:25 pm - 5:20 pm
ORD
-
YQR
23h 55m
1 stop
Multiple Airlines Logo
10:45 am - 7:09 pm
YQR
-
ORD
7h 24m
1 stop
$433Multiple Airlines
Thu, Jun 18 - Sun, Jun 21
Air Canada Logo
8:40 pm - 9:05 am
ORD
-
YQR
13h 25m
1 stop
Air Canada Logo
5:45 am - 2:55 pm
YQR
-
ORD
8h 10m
1 stop
$437Air Canada
Thu, Jun 18 - Sun, Jun 21
Multiple Airlines Logo
5:29 pm - 12:45 pm
ORD
-
YQR
20h 16m
2 stops
Multiple Airlines Logo
10:45 am - 5:19 pm
YQR
-
ORD
5h 34m
1 stop
$468Multiple Airlines
Sat, Jun 27 - Sat, Jul 4
Multiple Airlines Logo
5:30 pm - 9:45 am
ORD
-
YQR
17h 15m
1 stop
Multiple Airlines Logo
10:45 am - 5:19 pm
YQR
-
ORD
5h 34m
1 stop
$481Multiple Airlines
Sun, Jun 28 - Sat, Jul 4
United Airlines Logo
8:40 am - 9:30 pm
ORD
-
YQR
13h 50m
2 stops
United Airlines Logo
9:45 am - 12:58 am
YQR
-
ORD
14h 13m
1 stop
$489United Airlines
Wed, May 13 - Sun, May 17
Delta Logo
2:07 pm - 1:10 am
ORD
-
YQR
12h 03m
2 stops
Delta Logo
10:45 am - 7:31 pm
YQR
-
ORD
7h 46m
1 stop
$496Delta
Fri, Jun 19 - Sun, Jun 21

Delta flights from Chicago to Regina

Our best Delta deals on Chicago to Regina flight tickets
Delta
Jun 19
ORD2:07 pmChicago O'Hare Intl
12h 03m
2 stops
YQR1:10 amRegina
Jun 21
YQR10:45 amRegina
7h 46m
1 stop
ORD7:31 pmChicago O'Hare Intl
$496
Delta
May 6
ORD7:10 amChicago O'Hare Intl
11h 10m
2 stops
YQR5:20 pmRegina
May 9
YQR10:45 amRegina
12h 14m
2 stops
ORD11:59 pmChicago O'Hare Intl
$506
Delta
Jul 15
ORD11:30 amChicago O'Hare Intl
12h 50m
2 stops
YQR11:20 pmRegina
Jul 22
YQR10:45 amRegina
12h 08m
2 stops
ORD11:53 pmChicago O'Hare Intl
$600

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
Jun 18
ORD8:40 pmChicago O'Hare Intl
13h 25m
1 stop
YQR9:05 amRegina
Jun 21
YQR5:45 amRegina
8h 10m
1 stop
ORD2:55 pmChicago O'Hare Intl
$416
Air Canada
Jun 18
ORD8:40 pmChicago O'Hare Intl
13h 25m
1 stop
YQR9:05 amRegina
Jun 21
YQR5:45 amRegina
8h 10m
1 stop
ORD2:55 pmChicago O'Hare Intl
$437
Air Canada
Jun 27
ORD5:35 pmChicago O'Hare Intl
16h 30m
1 stop
YQR9:05 amRegina
Jul 4
YQR5:45 amRegina
6h 37m
1 stop
ORD1:22 pmChicago O'Hare Intl
$525

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 April 7, 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

Cheapest round-trip

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 5/13

3:00 pm-9:30 pm

1 stop7h 30m

Regina

Sun 5/17

9:45 am-12:58 am

1 stop14h 13m

$390

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 5/13

3:00 pm-9:30 pm

1 stop7h 30m

Regina

Sun 5/17

9:45 am-12:58 am

1 stop14h 13m

$411

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 6/18

8:40 pm-9:05 am

1 stop13h 25m

Regina

Sun 6/21

5:45 am-2:55 pm

1 stop8h 10m

$416

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 5/20

9:37 pm-5:20 pm

2 stops20h 43m

Regina

Wed 5/27

8:35 am-4:40 pm

1 stop7h 05m

$418

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 6/18

6:25 pm-5:20 pm

1 stop23h 55m

Regina

Sun 6/21

10:45 am-7:09 pm

1 stop7h 24m

$433

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 6/18

8:40 pm-9:05 am

1 stop13h 25m

Regina

Sun 6/21

5:45 am-2:55 pm

1 stop8h 10m

$437

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 6/27

5:29 pm-12:45 pm

2 stops20h 16m

Regina

Sat 7/4

10:45 am-5:19 pm

1 stop5h 34m

$468

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sun 6/28

5:30 pm-9:45 am

1 stop17h 15m

Regina

Sat 7/4

10:45 am-5:19 pm

1 stop5h 34m

$481

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 5/13

8:40 am-9:30 pm

2 stops13h 50m

Regina

Sun 5/17

9:45 am-12:58 am

1 stop14h 13m

$489
Quickest round-trip

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

2:07 pm-1:10 am

2 stops12h 03m

Regina

Sun 6/21

10:45 am-7:31 pm

1 stop7h 46m

$496

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 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 40% 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

5h 53m

Direct flights

None
The fastest flight from Chicago to Regina takes 5h 53m
There are no direct flights from Chicago to Regina. There are no popular flight routes from Chicago to Regina.
Search flight deals

Frequently asked questions about flying 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 5h 53m 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.

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 $86Free CancellationRating
7.4
9,550 reviews
Search United Airlines flights
DeltaPriceFrom $137Free CancellationRating
7.9
8,387 reviews
Search Delta flights
WestJetPriceFrom $330Free CancellationRating
7.2
3,316 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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