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$323+ Cheap flights from Chicago (CHI) to Regina (YQR)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YQR
Apr 23 — Apr 301
Thu 4/23
Thu 4/30
1 adult, Economy
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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 March 24, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/23. 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.
Tue 6/165:30 pm
ORD
-
YQR
1 stop8h 40m
WestJet
Tue 6/238:35 am
YQR
-
ORD
1 stop7h 05m
WestJet
Deal found 3/23$323
This Justfly.com deal was found by Cheapflights users on 3/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/165:30 pm
ORD
-
YQR
1 stop8h 40m
WestJet
Mon 6/227:00 pm
YQR
-
ORD
1 stop20h 40m
WestJet
Deal found 3/23$360
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/165:30 pm
ORD
-
YQR
1 stop8h 40m
Delta
Sat 6/2010:45 am
YQR
-
ORD
1 stop5h 17m
Delta
Deal found 3/23$411
This United Airlines deal was found by Cheapflights users on 3/19. 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 5/52:20 pm
ORD
-
YQR
1 stop8h 10m
United Airlines
Sat 5/99:45 am
YQR
-
ORD
1 stop13h 12m
United Airlines
Deal found 3/19$414
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/188:36 am
ORD
-
YQR
1 stop9h 44m
Delta
Sun 6/2110:45 am
YQR
-
ORD
1 stop7h 46m
Delta
Deal found 3/23$416
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/162:07 pm
ORD
-
YQR
2 stops12h 03m
Delta
Fri 6/1910:45 am
YQR
-
ORD
1 stop7h 46m
Delta
Deal found 3/23$421
This Air Canada deal was found by Cheapflights users on 3/22. 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 5/58:45 am
ORD
-
YQR
2 stops11h 22m
Air Canada
Sat 5/95:45 am
YQR
-
ORD
1 stop8h 10m
Air Canada
Deal found 3/22$424
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1312:46 pm
ORD
-
YQR
1 stop5h 34m
Delta
Wed 6/2410:45 am
YQR
-
ORD
2 stops8h 46m
Delta
Deal found 3/23$426
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/138:36 am
ORD
-
YQR
1 stop9h 44m
Delta
Tue 6/236:00 am
YQR
-
ORD
2 stops11h 29m
Delta
Deal found 3/23$429
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/162:07 pm
ORD
-
YQR
2 stops12h 03m
Delta
Wed 6/2410:45 am
YQR
-
ORD
2 stops8h 46m
Delta
Deal found 3/23$431
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/162:07 pm
ORD
-
YQR
2 stops12h 03m
Delta
Tue 6/236:00 am
YQR
-
ORD
2 stops11h 29m
Delta
Deal found 3/23$435

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 March 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$323
(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

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 March 24, 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

5:30 pm-1:10 am

1 stop8h 40m

Regina

Wed 6/24

10:45 am-5:02 pm

1 stop5h 17m

$411

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 5/5

2:20 pm-9:30 pm

1 stop8h 10m

Regina

Sat 5/9

9:45 am-11:57 pm

1 stop13h 12m

$414

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 5/5

1:43 pm-9:30 pm

1 stop8h 47m

Regina

Tue 5/12

9:45 am-11:57 pm

1 stop13h 12m

$414

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 6/18

8:36 am-5:20 pm

1 stop9h 44m

Regina

Sun 6/21

10:45 am-5:18 pm

1 stop5h 33m

$416
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-7:31 pm

1 stop7h 46m

$416

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 5/5

8:45 am-7:07 pm

2 stops11h 22m

Regina

Sat 5/9

5:45 am-2:55 pm

1 stop8h 10m

$424

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 6/13

8:36 am-5:20 pm

1 stop9h 44m

Regina

Tue 6/23

6:00 am-6:29 pm

2 stops11h 29m

$429

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 5/6

9:55 am-7:07 pm

1 stop10h 12m

Regina

Wed 5/13

5:45 am-1:25 pm

1 stop6h 40m

$440
Cheapest one-way
Quickest one-way

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 9/15

3:20 pm-11:20 pm

2 stops33h 00m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/23

Sorted by cheapest first
  • 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

What’s the top layover airport for flights from Chicago to Regina?

Share of 1-stop round-trip flights from Chicago to Regina chosen by Cheapflights users in the past 12 months, using the same layover each way.

Denver (DEN) – chosen by Cheapflights users on 60% of 1-stop itineraries from Chicago to Regina on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Regina?

Average round-trip fare for 1-stop flights from Chicago to Regina, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of $311.

What’s the fastest layover option from Chicago to Regina?

Shortest average travel time for 1-stop one-way flights from Chicago to Regina, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Calgary (YYC) have the shortest average one-way travel time for 1-stop routes: 6h 32m.

Which airport typically offers the quickest layover for flights from Chicago to Regina?

Average layover duration for 1-stop one-way flights from Chicago to Regina, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Calgary (YYC) offer the fastest connection on this route, with an average layover time of 1h 38m.

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 8h 10m. Fly via WestJet, Delta, or United Airlines 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.

  • 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

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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 March 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$303Average$387FlexibilityNo cancel feeOn-time69%
WestJetCheapest$330Average$373FlexibilityNo cancel feeOn-time60%

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