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Cheap flights from Chicago to Regina from $162

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 10/9. 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

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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 amORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
WestJet Logo
7:00 am - 4:40 pmYQR  Regina-ORD Chicago O'Hare Intl
8h 40m1 stop Calgary
$342WestJet
Thu, Sep 17 - Thu, Sep 24
Air Canada Logo
8:45 am - 7:05 pmORD  Chicago O'Hare Intl-YQR Regina
11h 20m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
5:45 am - 1:23 pmYQR  Regina-ORD Chicago O'Hare Intl
6h 38m1 stop Toronto Pearson Intl
$367Air Canada
Wed, Sep 16 - Wed, Sep 23
Multiple Airlines Logo
8:40 pm - 3:40 pmORD  Chicago O'Hare Intl-YQR Regina
20h 00m2 stops Toronto Pearson Intl Calgary
Multiple Airlines Logo
12:40 pm - 7:48 pmYQR  Regina-ORD Chicago O'Hare Intl
6h 08m1 stop Toronto Pearson Intl
$370Multiple Airlines
Wed, Sep 16 - Wed, Sep 23
Multiple Airlines Logo
8:40 pm - 12:45 pmORD  Chicago O'Hare Intl-YQR Regina
17h 05m2 stops Toronto Pearson Intl Calgary
Multiple Airlines Logo
8:35 am - 7:48 pmYQR  Regina-ORD Chicago O'Hare Intl
10h 13m2 stops Calgary Toronto Pearson Intl
$373Multiple Airlines
Wed, Sep 16 - Wed, Sep 23
United Airlines Logo
1:05 pm - 10:40 pmORD  Chicago O'Hare Intl-YQR Regina
9h 35m1 stop Denver Intl
United Airlines Logo
10:45 am - 6:38 pmYQR  Regina-ORD Chicago O'Hare Intl
7h 53m1 stop Denver Intl
$431United Airlines
Thu, Nov 19 - Mon, Nov 23
United Airlines Logo
7:00 am - 10:40 pmORD  Chicago O'Hare Intl-YQR Regina
15h 40m1 stop Denver Intl
United Airlines Logo
10:45 am - 9:10 pmYQR  Regina-ORD Chicago O'Hare Intl
10h 25m1 stop Denver Intl
$431United Airlines
Thu, Nov 19 - Wed, Nov 25
United Airlines Logo
8:40 am - 10:40 pmORD  Chicago O'Hare Intl-YQR Regina
14h 00m1 stop Denver Intl
United Airlines Logo
10:45 am - 11:59 pmYQR  Regina-ORD Chicago O'Hare Intl
13h 14m1 stop Denver Intl
$431United Airlines
Thu, Nov 19 - Tue, Nov 24
Delta Logo
8:04 am - 7:21 pmORD  Chicago O'Hare Intl-YQR Regina
11h 17m2 stops Atlanta Hartsfield-Jackson Minneapolis St Paul
Delta Logo
12:45 pm - 11:59 pmYQR  Regina-ORD Chicago O'Hare Intl
11h 14m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
$504Delta
Thu, Nov 19 - Mon, Nov 23
Delta Logo
9:53 am - 7:21 pmORD  Chicago O'Hare Intl-YQR Regina
9h 28m2 stops Atlanta Hartsfield-Jackson Minneapolis St Paul
Delta Logo
12:45 pm - 11:59 pmYQR  Regina-ORD Chicago O'Hare Intl
11h 14m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
$504Delta
Thu, Nov 19 - Tue, Nov 24
Delta Logo
5:30 am - 7:21 pmORD  Chicago O'Hare Intl-YQR Regina
13h 51m2 stops Atlanta Hartsfield-Jackson Minneapolis St Paul
Delta Logo
12:45 pm - 11:59 pmYQR  Regina-ORD Chicago O'Hare Intl
11h 14m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
$504Delta
Thu, Nov 19 - Wed, Nov 25

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WestJet flights from Chicago to Regina

Our best WestJet deals on Chicago to Regina flight tickets
WestJet
Sep 17
ORD5:30 pmChicago O'Hare Intl
8h 40m
1 stop
YQR1:10 amRegina
Sep 24
YQR7:00 amRegina
8h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
$342
WestJet
Sep 15
ORD5:30 pmChicago O'Hare Intl
18h 45m
3 stops
YQR11:15 amRegina
Sep 16
YQR8:20 pmRegina
19h 20m
2 stops
ORD4:40 pmChicago O'Hare Intl
$765
WestJet
Sep 19
ORD12:29 pmChicago O'Hare Intl
37h 06m
2 stops
YQR12:35 amRegina
Sep 26
YQR6:00 amRegina
13h 30m
2 stops
ORD8:30 pmChicago O'Hare Intl
$804

Air Canada flights from Chicago to Regina

Our best Air Canada deals on Chicago to Regina flight tickets
Air Canada
Sep 16
ORD8:45 amChicago O'Hare Intl
11h 20m
2 stops
YQR7:05 pmRegina
Sep 23
YQR5:45 amRegina
6h 38m
1 stop
ORD1:23 pmChicago O'Hare Intl
$367
Air Canada
Sep 17
ORD8:45 amChicago O'Hare Intl
11h 20m
2 stops
YQR7:05 pmRegina
Sep 24
YQR5:45 amRegina
8h 10m
1 stop
ORD2:55 pmChicago O'Hare Intl
$386
Air Canada
Sep 16
ORD8:45 amChicago O'Hare Intl
11h 20m
2 stops
YQR7:05 pmRegina
Sep 23
YQR12:40 pmRegina
6h 08m
1 stop
ORD7:48 pmChicago O'Hare Intl
$396

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 August 6, 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 Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Thu 9/17

5:30 pm-1:10 am

1 stop8h 40m

Regina

Thu 9/24

7:00 am-4:40 pm

1 stop8h 40m

$342

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Wed 9/16

8:45 am-7:05 pm

2 stops11h 20m

Regina

Wed 9/23

5:45 am-1:23 pm

1 stop6h 38m

$367

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Wed 9/16

8:40 pm-3:40 pm

2 stops20h 00m

Regina

Wed 9/23

12:40 pm-7:48 pm

1 stop6h 08m

$370

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Wed 9/16

8:40 pm-12:45 pm

2 stops17h 05m

Regina

Wed 9/23

8:35 am-7:48 pm

2 stops10h 13m

$373

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Thu 11/19

1:05 pm-10:40 pm

1 stop9h 35m

Regina

Mon 11/23

10:45 am-6:38 pm

1 stop7h 53m

$431

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Thu 11/19

7:00 am-10:40 pm

1 stop15h 40m

Regina

Wed 11/25

10:45 am-9:10 pm

1 stop10h 25m

$431

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Thu 11/19

8:40 am-10:40 pm

1 stop14h 00m

Regina

Tue 11/24

10:45 am-11:59 pm

1 stop13h 14m

$431

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Thu 11/19

8:04 am-7:21 pm

2 stops11h 17m

Regina

Mon 11/23

12:45 pm-11:59 pm

2 stops11h 14m

$504

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Thu 11/19

9:53 am-7:21 pm

2 stops9h 28m

Regina

Tue 11/24

12:45 pm-11:59 pm

2 stops11h 14m

$504

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Thu 11/19

5:30 am-7:21 pm

2 stops13h 51m

Regina

Wed 11/25

12:45 pm-11:59 pm

2 stops11h 14m

$504

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 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

7h 06m

Direct flights

None
The fastest flight from Chicago to Regina takes 7h 06m
There are no direct flights from Chicago to Regina. There are no popular flight routes from Chicago to Regina.
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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 7h 06m 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
8,491 reviews
Search Delta flights
United AirlinesPriceFrom $213Free CancellationRating
7.4
10,073 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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