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Cheap flights from Chicago to Regina from $205

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 6/20. 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.
Multiple Airlines Logo
8:19 pm - 5:20 pm
ORD
-
YQR
22h 01m
1 stop
Multiple Airlines Logo
10:45 am - 9:47 am
YQR
-
ORD
22h 02m
1 stop
$386Multiple Airlines
Wed, Jul 29 - Sun, Aug 30
Multiple Airlines Logo
8:19 pm - 5:20 pm
ORD
-
YQR
22h 01m
1 stop
Multiple Airlines Logo
9:05 pm - 5:12 pm
YQR
-
ORD
19h 07m
2 stops
$421Multiple Airlines
Wed, Jul 29 - Sun, Aug 30
WestJet Logo
5:30 pm - 1:10 am
ORD
-
YQR
8h 40m
1 stop
WestJet Logo
6:00 am - 4:40 pm
YQR
-
ORD
9h 40m
1 stop
$456WestJet
Tue, Aug 18 - Fri, Aug 21
Multiple Airlines Logo
6:31 pm - 5:20 pm
ORD
-
YQR
23h 49m
1 stop
Multiple Airlines Logo
10:45 am - 5:24 pm
YQR
-
ORD
5h 39m
1 stop
$471Multiple Airlines
Mon, Jun 22 - Mon, Jun 29
Multiple Airlines Logo
6:31 pm - 5:20 pm
ORD
-
YQR
23h 49m
1 stop
Multiple Airlines Logo
10:45 am - 5:24 pm
YQR
-
ORD
5h 39m
1 stop
$474Multiple Airlines
Mon, Jun 22 - Mon, Jun 29
WestJet Logo
5:30 pm - 11:15 am
ORD
-
YQR
18h 45m
2 stops
WestJet Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
$482WestJet
Tue, Aug 18 - Fri, Aug 21
Multiple Airlines Logo
6:31 pm - 5:20 pm
ORD
-
YQR
23h 49m
1 stop
Multiple Airlines Logo
10:45 am - 8:43 pm
YQR
-
ORD
32h 58m
2 stops
$483Multiple Airlines
Mon, Jun 22 - Mon, Jun 29
Multiple Airlines Logo
6:31 pm - 5:20 pm
ORD
-
YQR
23h 49m
1 stop
Multiple Airlines Logo
9:05 pm - 7:50 pm
YQR
-
ORD
21h 45m
2 stops
$485Multiple Airlines
Mon, Jun 22 - Mon, Jun 29
Air Canada Logo
8:45 am - 7:05 pm
ORD
-
YQR
11h 20m
2 stops
Air Canada Logo
5:45 am - 2:55 pm
YQR
-
ORD
8h 10m
1 stop
$489Air Canada
Tue, Oct 20 - Sat, Oct 24
Air Canada Logo
8:40 pm - 9:05 am
ORD
-
YQR
13h 25m
1 stop
Air Canada Logo
5:45 am - 1:22 pm
YQR
-
ORD
6h 37m
1 stop
$495Air Canada
Fri, Jun 19 - Sun, Jun 21

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
Oct 20
ORD8:45 amChicago O'Hare Intl
11h 20m
2 stops
YQR7:05 pmRegina
Oct 24
YQR5:45 amRegina
6h 38m
1 stop
ORD1:23 pmChicago O'Hare Intl
$489
Air Canada
Jun 19
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
$495
Air Canada
Oct 20
ORD8:40 pmChicago O'Hare Intl
13h 30m
1 stop
YQR9:10 amRegina
Oct 24
YQR12:40 pmRegina
6h 08m
1 stop
ORD7:48 pmChicago O'Hare Intl
$505

United Airlines flights from Chicago to Regina

Our best United Airlines deals on Chicago to Regina flight tickets
United Airlines
May 27
ORD7:05 amChicago O'Hare Intl
15h 25m
1 stop
YQR9:30 pmRegina
May 29
YQR9:45 amRegina
13h 59m
1 stop
ORD12:44 amChicago O'Hare Intl
$498
United Airlines
Oct 20
ORD12:58 pmChicago O'Hare Intl
7h 07m
1 stop
YQR7:05 pmRegina
Oct 24
YQR5:45 amRegina
7h 14m
1 stop
ORD1:59 pmChicago O'Hare Intl
$556
United Airlines
Jun 19
ORD8:50 amChicago O'Hare Intl
13h 40m
2 stops
YQR9:30 pmRegina
Jun 21
YQR5:45 amRegina
8h 10m
1 stop
ORD2:55 pmChicago O'Hare Intl
$665

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 May 10, 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 7/29

8:19 pm-5:20 pm

1 stop22h 01m

Regina

Sun 8/30

10:45 am-9:47 am

1 stop22h 02m

$386

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 7/29

8:19 pm-5:20 pm

1 stop22h 01m

Regina

Sun 8/30

9:05 pm-5:12 pm

2 stops19h 07m

$421
Quickest round-trip

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 8/18

5:30 pm-1:10 am

1 stop8h 40m

Regina

Fri 8/21

6:00 am-4:40 pm

1 stop9h 40m

$456

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 6/22

6:31 pm-5:20 pm

1 stop23h 49m

Regina

Mon 6/29

10:45 am-5:24 pm

1 stop5h 39m

$471

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 6/22

6:31 pm-5:20 pm

1 stop23h 49m

Regina

Mon 6/29

10:45 am-5:24 pm

1 stop5h 39m

$474

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 8/18

5:30 pm-11:15 am

2 stops18h 45m

Regina

Fri 8/21

8:35 am-4:40 pm

1 stop7h 05m

$482

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 6/22

6:31 pm-5:20 pm

1 stop23h 49m

Regina

Mon 6/29

10:45 am-8:43 pm

2 stops32h 58m

$483

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 6/22

6:31 pm-5:20 pm

1 stop23h 49m

Regina

Mon 6/29

9:05 pm-7:50 pm

2 stops21h 45m

$485

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 10/20

8:45 am-7:05 pm

2 stops11h 20m

Regina

Sat 10/24

5:45 am-2:55 pm

1 stop8h 10m

$489

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

8:40 pm-9:05 am

1 stop13h 25m

Regina

Sun 6/21

5:45 am-1:22 pm

1 stop6h 37m

$495

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 month to fly to Regina?

The month of August is another great option to travel to Regina, with average flight prices from Chicago averaging around $86.

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

7h 07m

Direct flights

None
The fastest flight from Chicago to Regina takes 7h 07m
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 7h 07m 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 $303Free CancellationRating
7.4
9,698 reviews
Search United Airlines flights
WestJetPriceFrom $330Free CancellationRating
7.2
3,332 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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