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$95+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YQR
Sep 5 — Sep 121
Fri 9/5
Fri 9/12
1 adult, Economy
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Cheap 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 31, 2025.

Round-trip from

$198
(oojo)

One-way from

$95
(United Airlines)
From Chicago (CHI) to Regina
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One-way flight from Chicago (CHI) to Regina
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Find 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 31, 2025.

This oojo deal was found by Cheapflights users on 8/31. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:30 pmORD - YQR
1 stop8h 47mWestJet
Sun 10/265:10 amYQR - ORD
1 stop7h 25mWestJet
Deal found 8/31$198
This United Airlines deal was found by Cheapflights users on 8/31. 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 11/61:55 pmORD - YQR
1 stop8h 56mUnited Airlines
Tue 11/1110:45 amYQR - ORD
1 stop6h 13mUnited Airlines
Deal found 8/31$239
This Air Canada deal was found by Cheapflights users on 8/31. 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 11/68:15 pmORD - YQR
1 stop14h 24mAir Canada
Tue 11/115:00 amYQR - ORD
2 stops15h 00mAir Canada
Deal found 8/31$266

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 31, 2025.
Use the filters below to find and compare flights from Chicago to Regina that are best for you.

Fly from

Chicago

Fly to

Regina

Route

Depart

Return

Price

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 10/23

5:30 pm-1:17 am

1 stop8h 47m

Regina

Sun 10/26

5:10 am-1:35 pm

1 stop7h 25m

$198

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 9/29

5:30 pm-1:17 am

1 stop8h 47m

Regina

Fri 10/3

6:55 am-4:43 pm

1 stop8h 48m

$224

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Fri 9/26

5:30 pm-10:57 am

1 stop18h 27m

Regina

Sun 10/5

6:55 am-4:43 pm

1 stop8h 48m

$224

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 9/23

5:30 pm-11:01 pm

1 stop6h 31m

Regina

Fri 10/3

8:35 am-4:43 pm

1 stop7h 08m

$224

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 9/29

5:30 pm-1:17 am

1 stop8h 47m

Regina

Sun 10/5

6:55 am-4:43 pm

1 stop8h 48m

$224

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 9/23

5:30 pm-1:17 am

1 stop8h 47m

Regina

Sun 10/5

6:55 am-4:43 pm

1 stop8h 48m

$224

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 9/25

2:23 pm-9:36 pm

1 stop8h 13m

Regina

Wed 10/8

9:45 am-10:39 pm

1 stop11h 54m

$239

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 9/23

7:15 am-9:36 pm

1 stop15h 21m

Regina

Thu 10/2

9:45 am-11:59 pm

1 stop13h 14m

$239

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Sat 9/27

2:53 pm-9:36 pm

1 stop7h 43m

Regina

Sat 10/4

9:45 am-6:26 pm

1 stop7h 41m

$239

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 9/25

2:53 pm-9:36 pm

1 stop7h 43m

Regina

Tue 10/7

9:45 am-10:39 pm

1 stop11h 54m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/31

Showing 1-10 of 12 results
1
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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.

Reviews of airlines servicing Regina

Get insights into the airlines that provide service to Regina. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Regina. Reviews last updated August 31, 2025.
Read reviews from past customers who have flown Delta and WestJet from Chicago to Regina. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,976 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,976 reviews
Delta
8.0
Very good
7,976 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
3,078 reviews
Delta
8.0
Very good
7,976 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 47m. Fly via WestJet to get the fastest option. Chicago and Regina are separated by a distance of 987 mi.

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

    Currently priced at $284, 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.

  • What is the cheapest month to book a flight from Chicago to Regina?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Regina (average of $288). Flying from Chicago to Regina in December is currently the most expensive (average of $586). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 Saskatoon flights
O'Hare Intl to Regina flights
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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 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$284Average$311FlexibilityNo cancel feeOn-time69%
WestJetCheapest$330Average$373FlexibilityNo cancel feeOn-time60%

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