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ORD - YQR

C$ 180 Find cheap flights from Chicago to Regina

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Regina departing on 17/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
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Search hundreds of travel sites at once for deals on flights to Regina

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Regina, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Regina, as well as popular online travel agencies
In the last 7 days, travellers have searched 45,017,868 times on KAYAK, and here is why:

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Cheap flight deals from Chicago to Regina (ORD-YQR)

 
These are the cheapest deals for flights from Chicago to Regina currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Regina

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Regina.

Recent one-way flight deals from Chicago to Regina

Only flying one-way? Below are some of the best one-way flight deals from Chicago to Regina found on KAYAK recently.

Recent last-minute flight deals from Chicago to Regina

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Chicago to Regina.

Recent direct flight deals from Chicago to Regina

The latest deals for direct flights from Chicago to Regina so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Chicago to Regina

Find recent round-trip train or bus tickets from Chicago to Regina.

All round-trip flight deals to Regina

The cheapest plane tickets to Regina found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
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4:50 p.m. - 5:36 p.m.ORD-YQR
24h 46m1 stop
11:45 a.m. - 7:05 p.m.YQR-ORD
7h 20m1 stop
C$ 895
Find Deal
Sun, 22 Dec - Sun, 29 Dec
6:30 a.m. - 12:56 a.m.ORD-YQR
18h 26m2 stops
11:45 a.m. - 7:05 p.m.YQR-ORD
7h 20m1 stop
C$ 995
Find Deal
Sun, 22 Dec - Sun, 29 Dec
12:40 p.m. - 5:39 p.m.ORD-YQR
28h 59m2 stops
5:00 a.m. - 6:48 p.m.YQR-ORD
37h 48m2 stops
C$ 1,228WestJet
Find Deal
Sun, 22 Dec - Sun, 29 Dec
4:00 p.m. - 11:18 p.m.ORD-YQR
7h 18m1 stop
6:45 a.m. - 6:43 p.m.YQR-ORD
11h 58m1 stop
C$ 1,435Air Canada
Find Deal
Sat, 21 Dec - Sat, 28 Dec
6:06 p.m. - 2:48 p.m.ORD-YQR
20h 42m2 stops
6:45 a.m. - 6:43 p.m.YQR-ORD
11h 58m1 stop
C$ 1,436Air Canada
Find Deal
Sat, 21 Dec - Sat, 28 Dec
6:06 p.m. - 2:48 p.m.ORD-YQR
20h 42m2 stops
4:20 p.m. - 8:05 a.m.YQR-ORD
15h 45m2 stops
C$ 1,602Air Canada
Find Deal
Sat, 21 Dec - Sat, 28 Dec
8:26 p.m. - 12:21 a.m.ORD-YQR
27h 55m3 stops
C$ 180
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Tue, 17 Dec
4:52 p.m. - 11:18 p.m.ORD-YQR
6h 26m1 stop
C$ 220United Airlines
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Tue, 17 Dec
8:03 p.m. - 5:36 p.m.ORD-YQR
21h 33m1 stop
C$ 306
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Sat, 28 Dec
10:45 a.m. - 11:18 p.m.ORD-YQR
12h 33m2 stops
C$ 317Air Canada
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Tue, 17 Dec
6:20 a.m. - 5:36 p.m.ORD-YQR
11h 16m1 stop
C$ 422WestJet
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Sun, 29 Dec
12:40 p.m. - 5:39 p.m.ORD-YQR
28h 59m2 stops
C$ 579WestJet
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Sun, 29 Dec
10:05 a.m. - 5:36 p.m.ORD-YQR
7h 31m1 stop
C$ 643Delta
Find Deal
Sat, 21 Dec
12:40 p.m. - 3:50 p.m.ORD-YQR
27h 10m2 stops
C$ 667WestJet
Find Deal
Sat, 28 Dec
6:30 a.m. - 12:21 a.m.ORD-YQR
17h 51m3 stops
C$ 743
Find Deal
Sun, 29 Dec
1:25 p.m. - 6:02 p.m.ORD-YQR
28h 37m2 stops
C$ 856United Airlines
Find Deal
Sat, 21 Dec

Flights from Chicago to Regina - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago to Regina to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Chicago to Regina?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago to Regina found by KAYAK users in the last 72 hours was for C$ 1,228 on WestJet, followed by Air Canada (C$ 1,435). One-way flight deals have also been found from as low as C$ 220 on United Airlines and from C$ 317 on Air Canada.

Good to know

Cheapest flight

C$ 180
Flight from Chicago to Regina

When to book flights from Chicago to Regina

Are your dates flexible? Find out the best times to travel from Chicago to Regina based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Regina flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Regina?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Regina was C$ 129 for a one-way ticket and C$ 643 for a round-trip.

  • Which airports will I be using when flying from Chicago to Regina?

    Chicago airport is called Chicago O'Hare Intl and the only airport in Regina is Regina.

  • Which aircraft models fly most regularly from Chicago to Regina?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Regina?

    Star Alliance, and SkyTeam are the airline alliances operating flights between Chicago and Regina, with Star Alliance being the most commonly used for this route.

  • How does KAYAK find such low prices on flights from Chicago to Regina?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Regina.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Regina?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Regina from Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Regina?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Regina with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Regina?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Regina from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Chicago to Regina

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Regina. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Regina? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.0
Air CanadaOverall score based on 8140 reviews
7.2Boarding
6.8Entertainment
6.2Food
7.8Crew
7.0Comfort
Airline reviews

This flight was a lot more comfortable with more room than the Air Canada Rouge!!! We will never go rouge again! A yes to this one!!! It was so nice to have inflight entertainment! Also the carts came around twice for drinks or a snack!! Great experience all around!

10.0 ExcellentMargaret, Nov 2024AUS - YYZ
Read more Air Canada reviews

This flight was a lot more comfortable with more room than the Air Canada Rouge!!! We will never go rouge again! A yes to this one!!! It was so nice to have inflight entertainment! Also the carts came around twice for drinks or a snack!! Great experience all around!

AC flight attendants aren't overly friendly. Otherwise flight was fine.

Newark to Montreal was really good. The return flight was not so good with a substitute carrier was not as good. I was impressed by the AC staff all along the way. Their in flight stack was superior.

I’m handicapped and the staff and crew were so kind and helped me board and made sure I was fine during the flight.

The people are great! The trip to Japan is simply never ending!!! Not the problem of the airlines, though.

I bought a ticket from Brussels to Fort Lauderdale, Florida, USA via Montreal. When I went to the airport, I learned that I needed a Canadian visa. When I bought the ticket online, there was no warning saying "If you are not a US or Canadian citizen; You need a Canadian visa." I asked for my money back, but the staff at the airport said they couldn't help me. I said, "Make the ticket open, I'll fly later," and they said no. I looked for this information on Air Canada's website. They've hidden it so well that it's impossible to find it easily. I understand that Air Canada makes millions of dollars in unfair profits by selling tickets this way. Why don't they ask when purchasing? They don't ask; because they're making money. Every year, perhaps thousands of tickets are subject to this situation. I will use all my rights and complain everywhere. Maybe they won't give me my money back, but I would advise anyone buying ticket to be careful from now on.

Friendlier staff who are nice to the elderly who need assistance

They intentionally delayed the flight by half an hour to accommodate a few fools who didn’t show up in time to clear customs. I missed my connector, missed an important meeting, and was charged a rebooking fee. Never again

Never flew with AirCanada before. Was a super duper flight every time and on time! No changes or delays!

Everything went very smoothly and the staff was courteous and friendly. I was really happy and pleased with how well the plane was flown because the departure, descent and landing were really smooth with no sudden drops. The plane’s interior was clean and nice and new in appearance.

Book cheap flights from Chicago to Regina

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Regina found on KAYAK in the last 72 hours.
17/12Tue
3 stops
27h 55mORD-YQR
C$ 180
17/12Tue
1 stopUnited Airlines
6h 26mORD-YQR
C$ 220
28/12Sat
1 stop
21h 33mORD-YQR
C$ 306
17/12Tue
2 stopsAir Canada
12h 33mORD-YQR
C$ 317
29/12Sun
1 stopWestJet
11h 16mORD-YQR
C$ 422
29/12Sun
2 stopsWestJet
28h 59mORD-YQR
C$ 579
21/12Sat
1 stopDelta
7h 31mORD-YQR
C$ 643
28/12Sat
2 stopsWestJet
27h 10mORD-YQR
C$ 667
29/12Sun
3 stops
17h 51mORD-YQR
C$ 743
21/12Sat
2 stopsUnited Airlines
28h 37mORD-YQR
C$ 856

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Everything you need to know for your flight from Chicago to Regina

Information on your arrival and departure airports