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Cheap flights from Chicago to Regina from $183

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 5/28. 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.
WestJet Logo
5:30 pm - 1:10 am
ORD
-
YQR
8h 40m
1 stop
WestJet Logo
7:00 am - 4:40 pm
YQR
-
ORD
8h 40m
1 stop
$316WestJet
Wed, May 27 - Wed, Jun 3
Multiple Airlines Logo
5:30 pm - 11:20 pm
ORD
-
YQR
6h 50m
1 stop
Multiple Airlines Logo
9:05 pm - 5:24 pm
YQR
-
ORD
19h 19m
2 stops
$393Multiple Airlines
Wed, May 27 - Wed, Jun 3
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
$398Multiple Airlines
Mon, Jun 22 - Mon, Jun 29
Multiple Airlines Logo
6:31 pm - 7:45 pm
ORD
-
YQR
26h 14m
2 stops
Multiple Airlines Logo
10:45 am - 10:27 am
YQR
-
ORD
22h 42m
1 stop
$404Multiple Airlines
Mon, Jun 22 - Mon, Jun 29
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
$408Multiple Airlines
Tue, May 26 - Tue, Jun 2
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
$423Multiple Airlines
Mon, Jun 22 - Mon, Jun 29
Multiple Airlines Logo
6:25 pm - 5:20 pm
ORD
-
YQR
23h 55m
1 stop
Multiple Airlines Logo
10:45 am - 5:19 pm
YQR
-
ORD
5h 34m
1 stop
$426Multiple Airlines
Mon, Jun 29 - Mon, Jul 6
Multiple Airlines Logo
9:17 am - 5:20 pm
ORD
-
YQR
33h 03m
2 stops
Multiple Airlines Logo
7:00 am - 4:40 pm
YQR
-
ORD
8h 40m
1 stop
$428Multiple Airlines
Sat, May 23 - Sat, May 30
Multiple Airlines Logo
9:22 am - 5:20 pm
ORD
-
YQR
32h 58m
2 stops
Multiple Airlines Logo
10:45 am - 5:24 pm
YQR
-
ORD
5h 39m
1 stop
$432Multiple Airlines
Tue, Jun 23 - Mon, Jun 29
United Airlines Logo
6:00 am - 9:30 pm
ORD
-
YQR
16h 30m
1 stop
United Airlines Logo
9:45 am - 8:05 pm
YQR
-
ORD
9h 20m
1 stop
$433United Airlines
Sat, May 23 - Sat, May 30

WestJet flights from Chicago to Regina

Our best WestJet deals on Chicago to Regina flight tickets
WestJet
May 27
ORD5:30 pmChicago O'Hare Intl
8h 40m
1 stop
YQR1:10 amRegina
Jun 3
YQR7:00 amRegina
8h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
$316
WestJet
Jun 19
ORD5:30 pmChicago O'Hare Intl
6h 50m
1 stop
YQR11:20 pmRegina
Jun 21
YQR11:50 amRegina
27h 50m
2 stops
ORD4:40 pmChicago O'Hare Intl
$612
WestJet
Jun 19
ORD5:30 pmChicago O'Hare Intl
27h 15m
2 stops
YQR7:45 pmRegina
Jun 21
YQR11:50 amRegina
27h 50m
2 stops
ORD4:40 pmChicago O'Hare Intl
$618

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
May 30
ORD9:55 amChicago O'Hare Intl
10h 12m
1 stop
YQR7:07 pmRegina
Jun 3
YQR5:45 amRegina
6h 40m
1 stop
ORD1:25 pmChicago O'Hare Intl
$441
Air Canada
Jun 19
ORD8:40 pmChicago O'Hare Intl
13h 25m
1 stop
YQR9:05 amRegina
Jun 21
YQR5:45 amRegina
6h 37m
1 stop
ORD1:22 pmChicago O'Hare Intl
$442
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
$459

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 13, 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
Quickest round-trip

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 5/27

5:30 pm-1:10 am

1 stop8h 40m

Regina

Wed 6/3

7:00 am-4:40 pm

1 stop8h 40m

$316

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 5/27

5:30 pm-11:20 pm

1 stop6h 50m

Regina

Wed 6/3

9:05 pm-5:24 pm

2 stops19h 19m

$393

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

$398

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 6/22

6:31 pm-7:45 pm

2 stops26h 14m

Regina

Mon 6/29

10:45 am-10:27 am

1 stop22h 42m

$404

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 5/26

9:37 pm-5:20 pm

2 stops20h 43m

Regina

Tue 6/2

8:35 am-4:40 pm

1 stop7h 05m

$408

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

$423

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 6/29

6:25 pm-5:20 pm

1 stop23h 55m

Regina

Mon 7/6

10:45 am-5:19 pm

1 stop5h 34m

$426

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 5/23

9:17 am-5:20 pm

2 stops33h 03m

Regina

Sat 5/30

7:00 am-4:40 pm

1 stop8h 40m

$428

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 6/23

9:22 am-5:20 pm

2 stops32h 58m

Regina

Mon 6/29

10:45 am-5:24 pm

1 stop5h 39m

$432

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 5/23

6:00 am-9:30 pm

1 stop16h 30m

Regina

Sat 5/30

9:45 am-8:05 pm

1 stop9h 20m

$433

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 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

8h 40m

Direct flights

None
The fastest flight from Chicago to Regina takes 8h 40m
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 8h 40m 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
9,581 reviews
Search United Airlines flights
DeltaPriceFrom $137Free CancellationRating
7.9
8,408 reviews
Search Delta flights
WestJetPriceFrom $330Free CancellationRating
7.2
3,320 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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