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Cheap flights from Chicago to Regina from $218

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 8/7. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Regina

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
10:50 am - 9:41 pm
ORD
-
YQR
11h 51m
1 stop
Multiple Airlines Logo
6:00 am - 2:56 pm
YQR
-
ORD
8h 56m
1 stop
$416Multiple Airlines
Sat, Oct 31 - Thu, Nov 5
WestJet Logo
2:20 pm - 10:45 am
ORD
-
YQR
21h 25m
1 stop
WestJet Logo
5:10 am - 1:35 pm
YQR
-
ORD
7h 25m
1 stop
$445WestJet
Sun, Oct 25 - Thu, Oct 29
United Airlines Logo
6:00 am - 9:30 pm
ORD
-
YQR
16h 30m
1 stop
United Airlines Logo
9:45 am - 9:18 pm
YQR
-
ORD
10h 33m
1 stop
$452United Airlines
Sat, Oct 17 - Tue, Oct 20
WestJet Logo
2:20 pm - 10:45 am
ORD
-
YQR
21h 25m
1 stop
WestJet Logo
5:10 am - 1:35 pm
YQR
-
ORD
7h 25m
1 stop
$461WestJet
Sun, Oct 25 - Thu, Oct 29
Air Canada Logo
8:45 am - 7:05 pm
ORD
-
YQR
11h 20m
2 stops
Air Canada Logo
12:40 pm - 7:48 pm
YQR
-
ORD
6h 08m
1 stop
$462Air Canada
Sat, Oct 17 - Tue, Oct 20
WestJet Logo
2:20 pm - 9:30 am
ORD
-
YQR
20h 10m
2 stops
WestJet Logo
5:10 pm - 1:35 pm
YQR
-
ORD
19h 25m
2 stops
$467WestJet
Sun, Oct 25 - Thu, Oct 29
Multiple Airlines Logo
7:15 am - 9:41 pm
ORD
-
YQR
15h 26m
1 stop
Multiple Airlines Logo
6:00 am - 12:56 pm
YQR
-
ORD
6h 56m
1 stop
$470Multiple Airlines
Thu, Oct 29 - Thu, Nov 5
Air Canada Logo
8:45 am - 7:05 pm
ORD
-
YQR
11h 20m
2 stops
Air Canada Logo
5:45 am - 8:12 pm
YQR
-
ORD
13h 27m
2 stops
$471Air Canada
Sat, Oct 17 - Tue, Oct 20
WestJet Logo
2:20 pm - 12:55 am
ORD
-
YQR
11h 35m
1 stop
WestJet Logo
8:45 pm - 1:35 pm
YQR
-
ORD
15h 50m
1 stop
$475WestJet
Sun, Oct 25 - Thu, Oct 29
United Airlines Logo
6:00 am - 9:30 pm
ORD
-
YQR
16h 30m
1 stop
United Airlines Logo
9:45 am - 12:44 am
YQR
-
ORD
13h 59m
1 stop
$476United Airlines
Thu, Jul 16 - Thu, Jul 23

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Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
Oct 17
ORD8:45 amChicago O'Hare Intl
11h 20m
2 stops
YQR7:05 pmRegina
Oct 20
YQR12:40 pmRegina
6h 08m
1 stop
ORD7:48 pmChicago O'Hare Intl
$462
Air Canada
Oct 17
ORD8:45 amChicago O'Hare Intl
11h 20m
2 stops
YQR7:05 pmRegina
Oct 20
YQR5:45 amRegina
13h 27m
2 stops
ORD8:12 pmChicago O'Hare Intl
$470
Air Canada
Oct 17
ORD8:45 amChicago O'Hare Intl
11h 20m
2 stops
YQR7:05 pmRegina
Oct 20
YQR5:45 amRegina
13h 27m
2 stops
ORD8:12 pmChicago O'Hare Intl
$471

Delta flights from Chicago to Regina

Our best Delta deals on Chicago to Regina flight tickets
Delta
Oct 29
ORD12:15 pmChicago O'Hare Intl
13h 40m
2 stops
YQR12:55 amRegina
Nov 5
YQR12:45 pmRegina
6h 49m
1 stop
ORD7:34 pmChicago O'Hare Intl
$503
Delta
Nov 19
ORD12:15 pmChicago O'Hare Intl
7h 06m
1 stop
YQR7:21 pmRegina
Nov 23
YQR10:40 amRegina
10h 54m
2 stops
ORD9:34 pmChicago O'Hare Intl
$520
Delta
Nov 19
ORD5:30 amChicago O'Hare Intl
13h 51m
2 stops
YQR7:21 pmRegina
Nov 23
YQR12:45 pmRegina
11h 05m
2 stops
ORD11:50 pmChicago O'Hare Intl
$536

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 June 27, 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

Sat 10/31

10:50 am-9:41 pm

1 stop11h 51m

Regina

Thu 11/5

6:00 am-2:56 pm

1 stop8h 56m

$416

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sun 10/25

2:20 pm-10:45 am

1 stop21h 25m

Regina

Thu 10/29

5:10 am-1:35 pm

1 stop7h 25m

$445

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 10/17

6:00 am-9:30 pm

1 stop16h 30m

Regina

Tue 10/20

9:45 am-9:18 pm

1 stop10h 33m

$452

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sun 10/25

2:20 pm-10:45 am

1 stop21h 25m

Regina

Thu 10/29

5:10 am-1:35 pm

1 stop7h 25m

$461
Quickest round-trip

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 10/17

8:45 am-7:05 pm

2 stops11h 20m

Regina

Tue 10/20

12:40 pm-7:48 pm

1 stop6h 08m

$462

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sun 10/25

2:20 pm-9:30 am

2 stops20h 10m

Regina

Thu 10/29

5:10 pm-1:35 pm

2 stops19h 25m

$467

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 10/29

7:15 am-9:41 pm

1 stop15h 26m

Regina

Thu 11/5

6:00 am-12:56 pm

1 stop6h 56m

$470

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 10/17

8:45 am-7:05 pm

2 stops11h 20m

Regina

Tue 10/20

5:45 am-8:12 pm

2 stops13h 27m

$471

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sun 10/25

2:20 pm-12:55 am

1 stop11h 35m

Regina

Thu 10/29

8:45 pm-1:35 pm

1 stop15h 50m

$475

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 7/16

6:00 am-9:30 pm

1 stop16h 30m

Regina

Thu 7/23

9:45 am-12:44 am

1 stop13h 59m

$476

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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 January is another great option to travel to Regina, with average flight prices from Chicago averaging around $0.

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
DeltaPriceFrom $137Free CancellationRating
7.8
8,451 reviews
Search Delta flights
United AirlinesPriceFrom $213Free CancellationRating
7.4
9,896 reviews
Search United Airlines 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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