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Regina

$156+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YQR
Sep 15 — Sep 221
Tue 9/15
Tue 9/22
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 August 16, 2026.

This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:30 pm -
1 stop8h 40m
Fri 8/288:35 am -
1 stop7h 05m
Deal found 8/14$345
This Trip.com deal was found by Cheapflights users on 8/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:30 pm -
1 stop6h 50m
Mon 10/57:00 am -
1 stop8h 40m
Deal found 8/14$346
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Mon 9/285:30 pm -
1 stop6h 50m
Mon 10/510:45 am -
2 stops36h 38m
Deal found 8/14$352
This Trip.com deal was found by Cheapflights users on 8/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/275:30 pm -
1 stop8h 40m
Sun 10/47:00 am -
1 stop8h 40m
Deal found 8/13$361

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 August 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$345
(Trip.com)

One-way from

$156
(FlightHub)
Provider with most accurate pricing for Chicago (CHI)-Regina flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Regina flights.
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From Chicago (CHI) to Regina
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One-way flight from Chicago (CHI) to Regina
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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 August 16, 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 Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Mon 9/28

5:30 pm-11:20 pm

1 stop6h 50m

Regina

Mon 10/5

10:45 am-12:23 am

2 stops36h 38m

$353

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Sun 9/27

11:05 am-10:50 am

3 stops24h 45m

Regina

Sun 10/4

5:45 am-1:23 pm

1 stop6h 38m

$419

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Tue 9/15

5:30 pm-6:25 pm

1 stop25h 55m

Regina

Fri 9/18

7:00 am-4:40 pm

1 stop8h 40m

$477

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Sun 9/27

5:30 pm-11:15 am

2 stops18h 45m

Regina

Sun 10/4

8:20 pm-4:40 pm

2 stops19h 20m

$517

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Thu 11/19

1:30 pm-10:40 pm

1 stop9h 10m

Regina

Tue 11/24

10:45 am-11:59 pm

1 stop13h 14m

$526

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

Wed 11/25

10:45 am-11:59 pm

1 stop13h 14m

$526
Quickest round-trip

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Thu 11/19

10:55 am-10:40 pm

1 stop11h 45m

Regina

Mon 11/23

10:45 am-6:38 pm

1 stop7h 53m

$526
Cheapest one-way
Quickest one-way

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Fri 9/11

5:30 pm-11:20 pm

1 stop6h 50m

$156

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Mon 9/28

5:30 pm-1:10 am

1 stop8h 40m

$187

ChicagoRegina

ORD Chicago O'Hare Intl - YQR Regina

ORDYQR

Chicago O'Hare Intl

Sun 9/27

5:30 pm-11:20 pm

1 stop30h 50m

$204

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

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.

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

    Currently priced at $137, Delta will fly you from Chicago to Regina and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as $213.

  • 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

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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 August 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$137Average$609FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$213Average$687FlexibilityNo cancel feeOn-time69%

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