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Cheap flights from Chicago to Regina from $114

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 11/28. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
1:55 pm - 9:51 pmORD-YQR
8h 56m1 stop
United Airlines Logo
10:45 am - 10:50 pmYQR-ORD
12h 05m1 stop
$234United Airlines
Find Deal
Thu, Oct 30 - Tue, Nov 4
Multiple Airlines Logo
6:14 pm - 6:20 pmORD-YQR
24h 06m1 stop
Multiple Airlines Logo
6:10 am - 5:32 amYQR-ORD
23h 22m2 stops
$275Multiple Airlines
Find Deal
Fri, Nov 7 - Wed, Nov 12
Multiple Airlines Logo
2:20 pm - 1:56 amORD-YQR
11h 36m1 stop
Multiple Airlines Logo
7:30 am - 9:47 amYQR-ORD
26h 17m3 stops
$328Multiple Airlines
Find Deal
Fri, Nov 7 - Wed, Nov 12
Delta Logo
8:57 am - 6:20 pmORD-YQR
9h 23m1 stop
Delta Logo
11:40 am - 9:36 pmYQR-ORD
9h 56m1 stop
$335Delta
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Thu, Nov 6 - Tue, Nov 11
Delta Logo
8:57 am - 6:20 pmORD-YQR
9h 23m1 stop
Delta Logo
11:40 am - 10:30 pmYQR-ORD
10h 50m2 stops
$345Delta
Find Deal
Thu, Nov 6 - Tue, Nov 11
Multiple Airlines Logo
9:22 pm - 1:56 amORD-YQR
28h 34m2 stops
Multiple Airlines Logo
7:30 am - 9:47 amYQR-ORD
26h 17m3 stops
$402Multiple Airlines
Find Deal
Fri, Nov 7 - Wed, Nov 12
Multiple Airlines Logo
9:22 pm - 1:56 amORD-YQR
28h 34m3 stops
Multiple Airlines Logo
7:30 am - 9:47 amYQR-ORD
26h 17m3 stops
$407Multiple Airlines
Find Deal
Fri, Nov 7 - Wed, Nov 12
Air Canada Logo
3:40 pm - 11:57 pmORD-YQR
9h 17m1 stop
Air Canada Logo
5:00 am - 6:33 pmYQR-ORD
12h 33m2 stops
$459Air Canada
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Tue, Apr 7 - Wed, Apr 8
Air Canada Logo
3:40 pm - 11:57 pmORD-YQR
9h 17m1 stop
Air Canada Logo
5:00 am - 6:33 pmYQR-ORD
12h 33m2 stops
$470Air Canada
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Tue, Apr 7 - Wed, Apr 8
WestJet Logo
2:20 pm - 9:35 amORD-YQR
20h 15m2 stops
WestJet Logo
9:45 pm - 6:49 pmYQR-ORD
21h 04m2 stops
$651WestJet
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Thu, Oct 30 - Tue, Nov 4

Delta flights from Chicago to Regina

Our best Delta deals on Chicago to Regina flight tickets
Delta
Nov 6
ORD8:57 amChicago O'Hare Intl
9h 23m
1 stop
YQR6:20 pmRegina
Nov 11
YQR11:40 amRegina
9h 56m
1 stop
ORD9:36 pmChicago O'Hare Intl
$335
Find similar
Delta
Nov 6
ORD8:57 amChicago O'Hare Intl
9h 23m
1 stop
YQR6:20 pmRegina
Nov 11
YQR11:40 amRegina
10h 50m
2 stops
ORD10:30 pmChicago O'Hare Intl
$345
Find similar
Delta
Oct 30
ORD2:20 pmChicago O'Hare Intl
10h 10m
1 stop
YQR11:30 pmRegina
Nov 4
YQR11:40 amRegina
12h 18m
2 stops
ORD11:58 pmChicago O'Hare Intl
$421
Find similar

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
Apr 7
ORD3:40 pmChicago O'Hare Intl
9h 17m
1 stop
YQR11:57 pmRegina
Apr 8
YQR5:00 amRegina
12h 33m
2 stops
ORD6:33 pmChicago O'Hare Intl
$459
Find similar
Air Canada
Apr 7
ORD3:40 pmChicago O'Hare Intl
9h 17m
1 stop
YQR11:57 pmRegina
Apr 8
YQR5:00 amRegina
12h 33m
2 stops
ORD6:33 pmChicago O'Hare Intl
$470
Find similar

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 October 14, 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

10:45 am-10:50 pm

1 stop12h 05m

$234

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 11/7

6:14 pm-6:20 pm

1 stop24h 06m

Regina

Wed 11/12

6:10 am-5:32 am

2 stops23h 22m

$275

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 11/7

2:20 pm-1:56 am

1 stop11h 36m

Regina

Wed 11/12

7:30 am-9:47 am

3 stops26h 17m

$328

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 11/6

8:57 am-6:20 pm

1 stop9h 23m

Regina

Tue 11/11

11:40 am-9:36 pm

1 stop9h 56m

$335

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 11/6

8:57 am-6:20 pm

1 stop9h 23m

Regina

Tue 11/11

11:40 am-10:30 pm

2 stops10h 50m

$345

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 11/7

9:22 pm-1:56 am

2 stops28h 34m

Regina

Wed 11/12

7:30 am-9:47 am

3 stops26h 17m

$402

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 11/7

9:22 pm-1:56 am

3 stops28h 34m

Regina

Wed 11/12

7:30 am-9:47 am

3 stops26h 17m

$407

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 4/7

3:40 pm-11:57 pm

1 stop9h 17m

Regina

Wed 4/8

5:00 am-6:33 pm

2 stops12h 33m

$459

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 4/7

3:40 pm-11:57 pm

1 stop9h 17m

Regina

Wed 4/8

5:00 am-6:33 pm

2 stops12h 33m

$470

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 10/30

2:20 pm-9:35 am

2 stops20h 15m

Regina

Tue 11/4

9:45 pm-6:49 pm

2 stops21h 04m

$651

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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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.
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  • 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 18m 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
8,977 reviews
Search United Airlines flights
WestJetPriceFrom $328Free CancellationRating
7.2
3,125 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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