HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Regina

$196+ Cheap flights from Chicago (CHI) to Regina (YQR)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YQR
Jun 14 — Jun 211
Sun 6/14
Sun 6/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Regina with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Regina

Cheapest flights from Chicago to Regina
Explore the most affordable flight options available from Chicago to Regina. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 15, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:25 pm
ORD
-
YQR
1 stop23h 55m
Multiple Airlines
Mon 6/88:35 am
YQR
-
ORD
1 stop7h 05m
Multiple Airlines
Deal found 5/13$398
This Trip.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:30 pm
ORD
-
YQR
1 stop8h 40m
WestJet
Tue 8/258:35 am
YQR
-
ORD
1 stop7h 05m
WestJet
Deal found 5/15$424
This Kiwi.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/226:31 pm
ORD
-
YQR
1 stop23h 49m
Multiple Airlines
Mon 6/2910:45 am
YQR
-
ORD
1 stop5h 39m
Multiple Airlines
Deal found 5/11$428
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:39 pm
ORD
-
YQR
1 stop23h 41m
Multiple Airlines
Wed 7/226:00 am
YQR
-
ORD
2 stops17h 49m
Multiple Airlines
Deal found 5/14$456
This United Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/62:33 pm
ORD
-
YQR
1 stop7h 57m
United Airlines
Mon 6/89:45 am
YQR
-
ORD
1 stop12h 04m
United Airlines
Deal found 5/13$468
This Air Canada deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/198:40 pm
ORD
-
YQR
1 stop13h 25m
Air Canada
Sun 6/215:45 am
YQR
-
ORD
1 stop8h 10m
Air Canada
Deal found 5/13$471
This United Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:00 am
ORD
-
YQR
1 stop16h 30m
United Airlines
Mon 6/299:45 am
YQR
-
ORD
1 stop12h 34m
United Airlines
Deal found 5/11$487
This Air Canada deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:45 am
ORD
-
YQR
2 stops11h 20m
Air Canada
Sat 10/245:45 am
YQR
-
ORD
1 stop8h 10m
Air Canada
Deal found 5/11$489

Find flight deals from Chicago to Regina

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Regina (YQR). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$398
(Kiwi.com)

One-way from

$196
(Kiwi.com)
Provider with most accurate pricing for Chicago (CHI)-Regina flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Regina flights.
Search Deals
From Chicago (CHI) to Regina
Search Deals
One-way flight from Chicago (CHI) to Regina
Search Deals

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated May 15, 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

Tue 6/16

2:33 pm-9:30 pm

1 stop7h 57m

Regina

Tue 6/23

9:45 am-12:44 am

1 stop13h 59m

$468

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

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 6/23

6:00 am-9:30 pm

1 stop16h 30m

Regina

Mon 6/29

9:45 am-11:19 pm

1 stop12h 34m

$487

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 10/20

8:45 am-7:05 pm

2 stops11h 20m

Regina

Sat 10/24

5:45 am-8:12 pm

2 stops13h 27m

$498

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 6/6

1:30 pm-9:30 pm

1 stop9h 00m

Regina

Mon 6/8

5:45 am-9:18 am

2 stops26h 33m

$542
Quickest round-trip

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

12:27 pm-5:20 pm

1 stop5h 53m

Regina

Sun 6/21

10:45 am-8:31 pm

2 stops8h 46m

$557

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 8/11

9:50 am-7:10 pm

1 stop10h 20m

Regina

Wed 8/12

5:45 am-1:22 pm

1 stop6h 37m

$557
Cheapest one-way

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 6/18

6:25 pm-5:20 pm

1 stop23h 55m

$196

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 6/20

7:05 am-9:30 pm

1 stop15h 25m

$210

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 6/19

6:25 pm-11:20 pm

3 stops29h 55m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/14

Showing 1-10 of 14 resultsSorted by cheapest first
1
2
  • Most accurate provider: When it comes to deals on Chicago-Regina flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Regina flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Regina flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Regina flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Regina flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Regina

Have a flexible travel schedule? Discover the best time to fly to Regina from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Regina
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Regina. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Regina from Chicago?

    Regina (YQR), located 2.5 mi from the city center, is the airport you fly into when you book flights from Chicago to Regina. 2 airlines have flights to Regina from Chicago on a regular basis. Booking flights from Chicago to Regina should not be difficult; the airport handles an average of 0 inbound flights from Chicago per day.

  • How long is the flight from Chicago to Regina?

    There are many flights that can get you from Chicago to Regina in 7h 57m. Fly via United Airlines or Air Canada to get the fastest option. Chicago and Regina are separated by a distance of 987 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Regina round-trip?

    Currently priced at $303, United Airlines will fly you from Chicago to Regina and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on WestJet for as low as $330.

  • Can I find deals for flights from Chicago to Regina that include hotel bookings?

    Yes. In addition to deals on Chicago to Regina flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Regina?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Regina.

  • Can I find deals for business class flights from Chicago to Regina?

    Yes. Cheapflights offers flight deals from Chicago to Regina by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Regina

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Regina flights
St. Louis to Saskatoon flights

Top 2 airlines flying from Chicago to Regina

Discover the top 2 airlines that operate flights from Chicago to Regina. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$303Average$391FlexibilityNo cancel feeOn-time69%
WestJetCheapest$330Average$373FlexibilityNo cancel feeOn-time60%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.