YQR - ORD

C$ 197 Find Cheap Flights from Regina to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Regina to Chicago departing on 28/9. 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
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Regina to Chicago, 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 Regina to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Regina to Chicago (YQR-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Regina to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Regina to Chicago

lun., 22 sep. - lun., 29 sep.
WestJet Logo
11:45 a.m. - 4:43 p.m.YQR-ORD
27h 58m1 stop
WestJet Logo
5:30 p.m. - 11:01 p.m.ORD-YQR
6h 31m1 stop
C$ 299WestJet
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lun., 22 sep. - lun., 29 sep.
WestJet Logo
5:30 p.m. - 4:43 p.m.YQR-ORD
22h 13m2 stops
WestJet Logo
5:30 p.m. - 11:01 p.m.ORD-YQR
6h 31m1 stop
C$ 309WestJet
Find Deal
vie., 21 nov. - lun., 24 nov.
United Airlines Logo
10:45 a.m. - 6:53 p.m.YQR-ORD
8h 08m1 stop
United Airlines Logo
1:55 p.m. - 10:51 p.m.ORD-YQR
8h 56m1 stop
C$ 381United Airlines
Find Deal
sáb., 8 nov. - sáb., 15 nov.
United Airlines Logo
10:45 a.m. - 6:53 p.m.YQR-ORD
8h 08m1 stop
United Airlines Logo
2:40 p.m. - 10:51 p.m.ORD-YQR
8h 11m1 stop
C$ 382United Airlines
Find Deal
dom., 5 oct. - jue., 9 oct.
 Logo
6:55 a.m. - 10:46 p.m.YQR-ORD
14h 51m2 stops
 Logo
5:30 p.m. - 11:01 p.m.ORD-YQR
6h 31m1 stop
C$ 420
Find Deal
lun., 6 oct. - jue., 9 oct.
Delta Logo
6:00 a.m. - 6:14 p.m.YQR-ORD
11h 14m2 stops
Delta Logo
5:30 p.m. - 11:01 p.m.ORD-YQR
6h 31m1 stop
C$ 434Delta
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lun., 6 oct. - dom., 12 oct.
Air Canada Logo
2:25 p.m. - 10:07 p.m.YQR-ORD
6h 42m1 stop
Air Canada Logo
7:10 a.m. - 1:28 p.m.ORD-YQR
7h 18m1 stop
C$ 465Air Canada
Find Deal
dom., 5 oct. - vie., 10 oct.
 Logo
6:55 a.m. - 10:46 p.m.YQR-ORD
14h 51m2 stops
 Logo
5:30 p.m. - 11:01 p.m.ORD-YQR
6h 31m1 stop
C$ 471
Find Deal
lun., 6 oct. - dom., 12 oct.
Delta Logo
6:00 a.m. - 8:23 p.m.YQR-ORD
13h 23m2 stops
Delta Logo
8:55 a.m. - 11:59 p.m.ORD-YQR
16h 04m2 stops
C$ 492Delta
Find Deal
dom., 5 oct. - dom., 12 oct.
Air Canada Logo
7:15 p.m. - 11:23 a.m.YQR-ORD
15h 08m2 stops
Air Canada Logo
7:10 a.m. - 1:28 p.m.ORD-YQR
7h 18m1 stop
C$ 514Air Canada
Find Deal
Booking Insights

KAYAK's insights & trends for Regina to Chicago flights

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

What is the cheapest month to fly from Regina to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Regina to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Regina to Chicago O'Hare Intl Airport is April, where tickets cost C$ 476 (return) on average. On the other hand, the most expensive months are February and June, where the average cost of round-trip tickets is C$ 1,610 and C$ 736 respectively.

Good to know

Low seasonJuly
Cheapest flightC$ 197
Best time to beat the crowds (19% less expensive on average)
Most popular time to fly and prices are also 5% lower on average.
Flight from Regina to Chicago

When to book flights from Regina to Chicago

Are your dates flexible? Find out the best times to travel from Regina to Chicago 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 Regina to Chicago flights

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

    In the last 3 days, the lowest price for a flight from Regina to Chicago O'Hare Intl Airport was C$ 143 for a one-way ticket and C$ 217 for a round-trip.

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

    Regina and Chicago are both served by 1 main airport. You will leave Regina from Regina and will be arriving at Chicago O'Hare Intl.

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

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

  • Which airline alliances offer flights from Regina to Chicago?

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

  • Which is the best airline for flights from Regina to Chicago, Delta or WestJet?

    The two airlines most popular with KAYAK users for flights from Regina to Chicago are Delta and WestJet. With an average price for the route of C$ 608 and an overall rating of 8.0, Delta is the most popular choice. WestJet is also a great choice for the route, with an average price of C$ 817 and an overall rating of 7.2.

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

    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 Regina to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Regina 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 Regina to Chicago?

    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 Chicago with an airline and back to Regina with another airline.

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

    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 Chicago from Regina up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines flying from Regina to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Regina to Chicago. 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 Regina to Chicago? 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.
8.0
DeltaOverall score based on 7982 reviews
8.2Boarding
7.9Entertainment
7.9Comfort
8.5Crew
7.3Food
Airline reviews

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

8.0 ExcellentJeanne, Aug 2025MSY - JFK
Read more Delta reviews

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

Our seats were comfortable with adequate room to stretch out and recline. The food was tasty and served it just the right intervals. Our flight attendant was extra attentive and friendly. Flight arrived early. And the most turbulence. Overall that’s good and experience for an 11 hour flight as can be hoped for

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

There was supposed to be a meal served, but there wasn’t and the major toilet was out of order

They made us board and then deboard due to mechanical issue which delayed the departure by almost 2 hours and we barely made our connecting flight. These quality checks should've been done before boarding not after.

Having to up charge for a seat assignment is not good. Delta can do better

I liked the friendliness of the staff. The cleanliness of all 3 planes.

Technology issues at the bag-check counter caused a delay, and we were unable to check out our bags, ultimately missing our flight. They offered no assistance other than telling us to book another flight out of Calgary. We arrived with plenty of time; if there hadn't been an issue with the kiosk and the length of the lines due to the technical issues, we could have made it home.

Worst check in and bag drop off experience. Staff were incredibly rude given that it’s the WestJet system that is faulty.

The staff at the airport and on the plane were wonderful I especially wanna acknowledge the staff who boarded us at the Calgary airport. The women who helped us board at the airport were incredible… they were so kind and sweet…I very happy with WestJet and I am hoping I can fly more often to Canada.

We were happy with our experience. The price for tickets was much less than Delta and we actually took off and landed a little ahead of scheduled times.

Seat back entertainment monitors would be nice. We did enjoy the In-Flight WiFi.

Our flight schedule was changed over six times, ultimately leaving us with a layover much shorter than we originally booked, which meant a panicked run through the airport. And the entertainment screen didn't function. As I've come to expect with Delta, a very mediocre and not customer-focused experience. This is on top of an outbound flight that was so delayed by mechanical issues, we had to spend the night at our layover city.

Staff were courteous and helpful. The only negative was the flight delays (which are usually unavoidable) and the high baggage price.

Absolutely terrible, from the customer service to boarding the plane. On the phone, there was some mishaps with getting in my correct date and they did not help me retrieve a refund or any assistance. I’m gonna be reporting to all my followers and family around the region of Los Angeles to New York.

Could not fly out of Canada. Called airlines on Monday, July 14th. Tried to cancel the flight 7 days away, but they said I could not cancel and there would be no refund.

A little disorganized but overall good. The Delta flights were great though

The AC could have been better . Other than that , all was good

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Very bad service the way back we was on the way for r two days very bad condition and waiting for luggage till now

Lack of WC assistance when returning to Toronto and my 92 year old aunt needed. To walk a fair distance with great difficulty to get to the exit and taxis. We were left without assistance after departing from the airport wagon.

United had no (zero) record of our flight. It took over an hour of us standing in line with surly employee while others waited to get resolved. I have never experienced such poor service and poor empathy.

Or the greatest and it ended up picking us up from Chicago to Toronto not sure who was tesponsible for the 4 hr delay. United should have been properly prepared for a scheduled flight from Austin to Chicago and they were not.

My flight was overbooked and they would not let me board. I had to book another flight and pay the full amount of that flight. I did not get any help at all from Air Canada or United Airlines.

Everything was made rather simple, so I appreciate that. All the people I dealt with from entering the airport in Jacksonville to my lonnnnnnng walk to my next gate in Chicago were excellent and very helpful.

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

It was okay; however, for a long-haul flight, the economy seats were uncomfortable. The seat cushioning needs to be improved. The food served was below average. The staff was good and courteous. They were attentive and helped the passengers where possible.

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

Information on your arrival and departure airports

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