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$268+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YQR
Jan 5 — Jan 121
Mon 1/5
Mon 1/12
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 December 6, 2025.

This oojo deal was found by Cheapflights users on 12/3. 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.
Mon 12/82:20 pmORD - YQR
2 stops20h 14mWestJet
Fri 12/126:10 amYQR - ORD
1 stop7h 25mWestJet
Deal found 12/3$719
This United Airlines deal was found by Cheapflights users on 12/4. 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.
Mon 12/88:50 amORD - YQR
2 stops14h 07mUnited Airlines
Fri 12/1210:53 amYQR - ORD
2 stops22h 48mUnited Airlines
Deal found 12/4$838

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 December 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$268
(Kissandfly.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
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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 December 6, 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

Mon 1/26

2:20 pm-9:08 pm

1 stop6h 48m

Regina

Tue 2/3

5:00 am-1:01 pm

1 stop8h 01m

$268

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Tue 1/20

12:53 pm-10:51 pm

1 stop9h 58m

Regina

Tue 1/27

10:45 am-5:04 pm

1 stop6h 19m

$335

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Wed 3/4

8:40 pm-10:39 am

1 stop13h 59m

Regina

Sun 3/8

5:00 am-1:01 pm

1 stop7h 01m

$357

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Thu 3/5

12:05 pm-1:15 am

2 stops13h 10m

Regina

Sun 3/8

8:45 pm-1:35 pm

1 stop15h 50m

$369

ChicagoRegina

ORD - YQR

ORDYQR

Chicago O'Hare Intl

Mon 1/26

3:35 pm-10:39 am

2 stops19h 04m

Regina

Tue 2/3

5:00 am-8:10 pm

2 stops15h 10m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Compare providers for flights from Chicago to Regina

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Regina in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Regina flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Regina flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

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 December 6, 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
7.9
Good
8,009 reviews

Entertainment

7.9

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,009 reviews
Delta
7.9
Good
8,009 reviews

Entertainment

7.9

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
WestJet
7.2
Good
3,193 reviews
Delta
7.9
Good
8,009 reviews

Entertainment

7.9

Overall

7.9

Crew

8.5

Comfort

7.9

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 9h 58m. 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 $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 $328.

  • 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.
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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 December 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$284Average$336FlexibilityNo cancel feeOn-time69%
WestJetCheapest$328Average$373FlexibilityNo cancel feeOn-time60%

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