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Cheap flights from Chicago to Regina from $105

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 5/26. 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
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
$333WestJet
Wed, May 27 - Fri, May 29
Multiple Airlines Logo
6:31 pm - 5:20 pm
ORD
-
YQR
23h 49m
1 stop
Multiple Airlines Logo
7:00 am - 10:27 am
YQR
-
ORD
26h 27m
2 stops
$379Multiple 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 - 10:27 am
YQR
-
ORD
22h 42m
1 stop
$380Multiple 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 - 7:09 pm
YQR
-
ORD
7h 24m
1 stop
$404Multiple Airlines
Thu, Jun 18 - Sun, Jun 21
Air Canada Logo
9:55 am - 7:07 pm
ORD
-
YQR
10h 12m
1 stop
Air Canada Logo
5:45 am - 8:08 pm
YQR
-
ORD
13h 23m
2 stops
$408Air Canada
Wed, May 27 - Fri, May 29
Multiple Airlines Logo
6:25 pm - 5:20 pm
ORD
-
YQR
23h 55m
1 stop
Multiple Airlines Logo
6:00 am - 12:48 am
YQR
-
ORD
17h 48m
2 stops
$410Multiple Airlines
Fri, Jun 19 - Tue, Jun 23
Multiple Airlines Logo
7:20 am - 5:20 pm
ORD
-
YQR
35h 00m
2 stops
Multiple Airlines Logo
10:45 am - 5:24 pm
YQR
-
ORD
5h 39m
1 stop
$417Multiple Airlines
Wed, Jun 24 - Wed, Jul 1
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
$438Air Canada
Fri, Jun 19 - Sun, Jun 21
Multiple Airlines Logo
6:31 pm - 5:20 pm
ORD
-
YQR
23h 49m
1 stop
Multiple Airlines Logo
7:00 am - 4:40 pm
YQR
-
ORD
8h 40m
1 stop
$445Multiple Airlines
Mon, Jul 13 - Tue, Sep 15
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
$471Air 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
May 27
ORD9:55 amChicago O'Hare Intl
10h 12m
1 stop
YQR7:07 pmRegina
May 29
YQR5:45 amRegina
13h 23m
2 stops
ORD8:08 pmChicago O'Hare Intl
$408
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
$438
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
$471

Delta flights from Chicago to Regina

Our best Delta deals on Chicago to Regina flight tickets
Delta
Jun 9
ORD8:36 amChicago O'Hare Intl
9h 44m
1 stop
YQR5:20 pmRegina
Jun 16
YQR10:45 amRegina
9h 40m
1 stop
ORD9:25 pmChicago O'Hare Intl
$502
Delta
Jun 9
ORD7:01 amChicago O'Hare Intl
11h 19m
2 stops
YQR5:20 pmRegina
Jun 16
YQR10:45 amRegina
9h 40m
1 stop
ORD9:25 pmChicago O'Hare Intl
$523
Delta
Jun 9
ORD7:01 amChicago O'Hare Intl
11h 19m
2 stops
YQR5:20 pmRegina
Jun 16
YQR6:00 amRegina
11h 29m
2 stops
ORD6:29 pmChicago O'Hare Intl
$547

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 3, 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

Fri 5/29

8:35 am-4:40 pm

1 stop7h 05m

$333

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 6/22

6:31 pm-5:20 pm

1 stop23h 49m

Regina

Mon 6/29

7:00 am-10:27 am

2 stops26h 27m

$379

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-10:27 am

1 stop22h 42m

$380

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

$404

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 5/27

9:55 am-7:07 pm

1 stop10h 12m

Regina

Fri 5/29

5:45 am-8:08 pm

2 stops13h 23m

$408

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

6:25 pm-5:20 pm

1 stop23h 55m

Regina

Tue 6/23

6:00 am-12:48 am

2 stops17h 48m

$410

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 6/24

7:20 am-5:20 pm

2 stops35h 00m

Regina

Wed 7/1

10:45 am-5:24 pm

1 stop5h 39m

$417

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

$438

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 7/13

6:31 pm-5:20 pm

1 stop23h 49m

Regina

Tue 9/15

7:00 am-4:40 pm

1 stop8h 40m

$445

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-2:55 pm

1 stop8h 10m

$471

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

6h 57m

Direct flights

None
The fastest flight from Chicago to Regina takes 6h 57m
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 6h 57m 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
9,684 reviews
Search United Airlines flights
WestJetPriceFrom $330Free CancellationRating
7.2
3,331 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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