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$178+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YQR
Jul 30 — Aug 61
Thu 7/30
Thu 8/6
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 June 30, 2026.

This United Airlines deal was found by Cheapflights users on 6/28. 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 10/176:00 am
ORD
-
YQR
1 stop16h 30m
United Airlines
Tue 10/209:45 am
YQR
-
ORD
1 stop10h 33m
United Airlines
Deal found 6/28$452
This United deal was found by Cheapflights users on 6/27. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:55 am
ORD
-
YQR
1 stop16h 35m
Multiple Airlines
Tue 9/85:45 am
YQR
-
ORD
1 stop8h 10m
Multiple Airlines
Deal found 6/27$459
This Air Canada deal was found by Cheapflights users on 6/27. 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.
Sat 10/178:45 am
ORD
-
YQR
2 stops11h 20m
Air Canada
Tue 10/2012:40 pm
YQR
-
ORD
1 stop6h 08m
Air Canada
Deal found 6/27$462
This United Airlines deal was found by Cheapflights users on 6/29. 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.
Thu 7/166:00 am
ORD
-
YQR
1 stop16h 30m
United Airlines
Thu 7/239:45 am
YQR
-
ORD
1 stop13h 59m
United Airlines
Deal found 6/29$476
This Air Canada deal was found by Cheapflights users on 6/27. 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.
Thu 11/198:35 pm
ORD
-
YQR
1 stop14h 08m
Air Canada
Mon 11/235:00 am
YQR
-
ORD
1 stop8h 13m
Air Canada
Deal found 6/27$477
This Delta deal was found by Cheapflights users on 6/29. 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 8/135:30 pm
ORD
-
YQR
1 stop8h 40m
Delta
Fri 8/218:35 am
YQR
-
ORD
1 stop7h 05m
Delta
Deal found 6/29$530
This Delta deal was found by Cheapflights users on 6/27. 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 11/195:30 am
ORD
-
YQR
2 stops13h 51m
Delta
Mon 11/2312:45 pm
YQR
-
ORD
2 stops11h 05m
Delta
Deal found 6/27$536
This WestJet deal was found by Cheapflights users on 6/24. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/252:20 pm
ORD
-
YQR
2 stops20h 10m
WestJet
Thu 10/295:10 am
YQR
-
ORD
1 stop7h 25m
WestJet
Deal found 6/24$540

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 June 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$452
(United Airlines)

One-way from

$178
(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.
Search Deals
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 June 30, 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

Sat 10/17

6:00 am-9:30 pm

1 stop16h 30m

Regina

Tue 10/20

9:45 am-9:18 pm

1 stop10h 33m

$452

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 9/3

5:55 am-9:30 pm

1 stop16h 35m

Regina

Tue 9/8

5:45 am-2:55 pm

1 stop8h 10m

$459
Quickest round-trip

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 10/17

8:45 am-7:05 pm

2 stops11h 20m

Regina

Tue 10/20

12:40 pm-7:48 pm

1 stop6h 08m

$462

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 7/16

6:00 am-9:30 pm

1 stop16h 30m

Regina

Thu 7/23

9:45 am-12:44 am

1 stop13h 59m

$476

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 11/19

8:35 pm-10:43 am

1 stop14h 08m

Regina

Mon 11/23

5:00 am-1:13 pm

1 stop8h 13m

$477
Cheapest one-way

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 10/9

5:30 pm-1:10 am

1 stop8h 40m

$178
Quickest one-way

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 9/3

2:42 pm-9:30 pm

1 stop7h 48m

$207

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 8/5

1:30 pm-9:30 pm

1 stop9h 00m

$211

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 8/5

5:30 pm-7:45 pm

2 stops27h 15m

$218

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sun 7/19

6:00 am-9:30 pm

1 stop16h 30m

$230

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

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 11h 20m. 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 $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 June 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$137Average$609FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$213Average$709FlexibilityNo cancel feeOn-time69%

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