Cheap flights from Chicago to Regina from $222

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 10/30. 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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Cheap round-trip flights

United Airlines Logo
1:55 pm - 9:51 pmORD-YQR
8h 56m1 stop
United Airlines Logo
5:00 am - 1:01 pmYQR-ORD
8h 01m1 stop
$222United Airlines
Find Deal
Thu, Oct 30 - Tue, Nov 4
United Airlines Logo
7:10 am - 9:36 pmORD-YQR
15h 26m1 stop
United Airlines Logo
11:25 am - 7:24 pmYQR-ORD
6h 59m1 stop
$237United Airlines
Find Deal
Wed, Oct 8 - Wed, Oct 15
United Airlines Logo
6:28 pm - 9:39 amORD-YQR
16h 11m1 stop
United Airlines Logo
5:00 am - 12:05 pmYQR-ORD
7h 05m1 stop
$248United Airlines
Find Deal
Thu, Oct 30 - Tue, Nov 4
United Airlines Logo
6:28 pm - 10:39 amORD-YQR
16h 11m1 stop
United Airlines Logo
10:45 am - 8:58 pmYQR-ORD
10h 13m1 stop
$251United Airlines
Find Deal
Thu, Nov 6 - Tue, Nov 11
Air Canada Logo
8:15 pm - 10:39 amORD-YQR
14h 24m1 stop
Air Canada Logo
5:00 am - 8:00 pmYQR-ORD
15h 00m2 stops
$253Air Canada
Find Deal
Thu, Nov 6 - Tue, Nov 11
 Logo
2:20 pm - 10:45 amORD-YQR
21h 25m1 stop
 Logo
4:25 pm - 6:25 amYQR-ORD
14h 00m2 stops
Thu, Oct 30 - Tue, Nov 4
Air Canada Logo
12:50 pm - 9:39 amORD-YQR
21h 49m2 stops
Air Canada Logo
5:00 am - 1:01 pmYQR-ORD
8h 01m1 stop
$286Air Canada
Find Deal
Thu, Oct 30 - Tue, Nov 4
 Logo
2:20 pm - 8:08 pmORD-YQR
6h 48m1 stop
 Logo
7:05 am - 6:25 amYQR-ORD
23h 20m3 stops
Thu, Oct 30 - Tue, Nov 4
Delta Logo
10:30 am - 11:01 pmORD-YQR
13h 31m2 stops
Delta Logo
6:00 am - 8:23 pmYQR-ORD
13h 23m2 stops
$393Delta
Find Deal
Wed, Oct 8 - Wed, Oct 15
Delta Logo
5:20 am - 6:20 pmORD-YQR
14h 00m2 stops
Delta Logo
11:45 am - 11:58 pmYQR-ORD
12h 13m2 stops
$611Delta
Find Deal
Thu, Oct 30 - Tue, Nov 4

United Airlines flights from Chicago to Regina

Our best United Airlines deals on Chicago to Regina flight tickets
United Airlines
Oct 30
ORD1:55 pmChicago O'Hare Intl
8h 56m
1 stop
YQR9:51 pmRegina
Nov 4
YQR5:00 amRegina
8h 01m
1 stop
ORD1:01 pmChicago O'Hare Intl
United Airlines
Oct 8
ORD7:10 amChicago O'Hare Intl
15h 26m
1 stop
YQR9:36 pmRegina
Oct 15
YQR11:25 amRegina
6h 59m
1 stop
ORD7:24 pmChicago O'Hare Intl
United Airlines
Oct 30
ORD6:28 pmChicago O'Hare Intl
16h 11m
1 stop
YQR9:39 amRegina
Nov 4
YQR5:00 amRegina
7h 05m
1 stop
ORD12:05 pmChicago O'Hare Intl

WestJet flights from Chicago to Regina

Our best WestJet deals on Chicago to Regina flight tickets
WestJet
Sep 20
ORD1:40 pmChicago O'Hare Intl
20h 50m
1 stop
YQR9:30 amRegina
Oct 4
YQR11:45 amRegina
27h 58m
1 stop
ORD4:43 pmChicago O'Hare Intl
WestJet
Sep 22
ORD5:30 pmChicago O'Hare Intl
41h 00m
2 stops
YQR9:30 amRegina
Sep 26
YQR10:15 amRegina
5h 32m
1 stop
ORD4:47 pmChicago O'Hare Intl
WestJet
Sep 22
ORD5:30 pmChicago O'Hare Intl
17h 00m
2 stops
YQR9:30 amRegina
Sep 26
YQR5:30 pmRegina
18h 09m
1 stop
ORD12:39 pmChicago O'Hare Intl

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 September 15, 2025.
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

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 10/30

1:55 pm-9:51 pm

1 stop8h 56m

Regina

Tue 11/4

5:00 am-1:01 pm

1 stop8h 01m

$222

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 10/8

7:10 am-9:36 pm

1 stop15h 26m

Regina

Wed 10/15

11:25 am-7:24 pm

1 stop6h 59m

$237

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 10/30

6:28 pm-9:39 am

1 stop16h 11m

Regina

Tue 11/4

5:00 am-12:05 pm

1 stop7h 05m

$248

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 11/6

6:28 pm-10:39 am

1 stop16h 11m

Regina

Tue 11/11

10:45 am-8:58 pm

1 stop10h 13m

$251

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 11/6

8:15 pm-10:39 am

1 stop14h 24m

Regina

Tue 11/11

5:00 am-8:00 pm

2 stops15h 00m

$253

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 10/30

2:20 pm-10:45 am

1 stop21h 25m

Regina

Tue 11/4

4:25 pm-6:25 am

2 stops14h 00m

$275

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 10/30

12:50 pm-9:39 am

2 stops21h 49m

Regina

Tue 11/4

5:00 am-1:01 pm

1 stop8h 01m

$286

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 10/30

2:20 pm-8:08 pm

1 stop6h 48m

Regina

Tue 11/4

7:05 am-6:25 am

3 stops23h 20m

$288

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 10/8

10:30 am-11:01 pm

2 stops13h 31m

Regina

Wed 10/15

6:00 am-8:23 pm

2 stops13h 23m

$393

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 10/30

5:20 am-6:20 pm

2 stops14h 00m

Regina

Tue 11/4

11:45 am-11:58 pm

2 stops12h 13m

$611

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 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 day to depart on your flight to Regina?

The cheapest day to depart from Chicago to Regina is on a Wednesday when prices can be found for as low as $348. Flights from Chicago to Regina on a Sunday will generally be more expensive and average around $1,034. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Regina?

The cheapest time of day to fly to Regina is in the afternoon when flights can be purchased for as low as $283. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $576 on average. Flights to Regina from Chicago in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

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

Direct flights

None
There are no direct flights from Chicago to Regina. There are no popular flight routes 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 48m 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.

  • What is the most popular airline from Chicago to Regina?

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 $284Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights
WestJetPriceFrom $328Free CancellationRating
7.2
3,091 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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1 adult
Wed 10/15
Wed 10/22

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