YQR - ORD

C$ 309 Find Cheap Flights from Regina to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Regina to Chicago departing on 16/6. 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

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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Cheap Flight Deals 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.

Recent round-trip flight deals from Regina to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Regina to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
 Logo
9:45 a.m. - 10:41 p.m.YQR-ORD
11h 56m1 stop
 Logo
8:25 p.m. - 10:30 a.m.ORD-YQR
15h 05m1 stop
C$ 309
Find Deal
Mon, 16 Jun - Thu, 19 Jun
Air Canada Logo
7:15 p.m. - 9:59 a.m.YQR-ORD
13h 44m1 stop
Air Canada Logo
8:25 p.m. - 10:30 a.m.ORD-YQR
15h 05m1 stop
C$ 410Air Canada
Find Deal
Tue, 24 Jun - Mon, 30 Jun
 Logo
10:15 a.m. - 5:09 p.m.YQR-ORD
5h 54m1 stop
 Logo
5:30 p.m. - 11:02 p.m.ORD-YQR
6h 32m1 stop
C$ 474
Find Deal
Mon, 28 Jul - Sat, 2 Aug
WestJet Logo
8:35 a.m. - 4:44 p.m.YQR-ORD
7h 09m1 stop
WestJet Logo
5:30 p.m. - 1:07 a.m.ORD-YQR
8h 37m1 stop
C$ 478WestJet
Find Deal
Tue, 13 May - Sun, 18 May
 Logo
6:55 a.m. - 4:44 p.m.YQR-ORD
8h 49m1 stop
 Logo
5:01 a.m. - 4:30 p.m.ORD-YQR
12h 29m2 stops
C$ 505
Find Deal
Mon, 16 Jun - Thu, 19 Jun
 Logo
10:15 a.m. - 5:15 p.m.YQR-ORD
6h 00m1 stop
 Logo
5:30 p.m. - 11:02 p.m.ORD-YQR
6h 32m1 stop
C$ 558
Find Deal
Sun, 27 Jul - Sat, 2 Aug
WestJet Logo
5:30 p.m. - 4:44 p.m.YQR-ORD
22h 14m2 stops
WestJet Logo
5:30 p.m. - 11:02 p.m.ORD-YQR
6h 32m1 stop
C$ 601WestJet
Find Deal
Sun, 27 Jul - Sat, 2 Aug
United Airlines Logo
9:45 a.m. - 12:25 a.m.YQR-ORD
13h 40m1 stop
United Airlines Logo
7:24 a.m. - 9:36 p.m.ORD-YQR
15h 12m2 stops
C$ 666United Airlines
Find Deal
Tue, 24 Jun - Mon, 30 Jun
Delta Logo
10:15 a.m. - 11:55 p.m.YQR-ORD
12h 40m2 stops
Delta Logo
5:30 p.m. - 1:07 a.m.ORD-YQR
8h 37m1 stop
C$ 690Delta
Find Deal
Mon, 28 Jul - Sun, 3 Aug
United Airlines Logo
9:45 a.m. - 6:25 p.m.YQR-ORD
7h 40m1 stop
United Airlines Logo
8:25 p.m. - 10:30 a.m.ORD-YQR
15h 05m1 stop
C$ 856United Airlines
Find Deal
Mon, 23 Jun - Mon, 23 Jun

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 May, where tickets cost C$ 465 (return) on average. On the other hand, the most expensive months are February and September, where the average cost of round-trip tickets is C$ 1,618 and C$ 741 respectively.

Good to know

Low season

May

High season

August

Cheapest flight

C$ 309
Best time to beat the crowds (33% less expensive on average)
Most popular time to fly and prices are also 16% 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$ 223 for a round-trip ticket.

  • 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$ 552 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$ 699 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.

See more FAQs

Top 3 airlines serving 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 7919 reviews
7.9Comfort
8.5Crew
7.9Entertainment
8.2Boarding
7.3Food
Airline reviews

Delta flight was on time, seats were comfortable, and crew was nice.

8.0 ExcellentAnonymous, Apr 2025LAX - DEN
Read more Delta reviews

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

I love the free WiFi!! Crew was nice. Bathroom was decent. First time flying delta in a long time and I enjoyed it. Will definitely look into booking with Delta more but I think Delta is a little more expensive than the other airlines.

third trip overseas with delta recently where the TV did not work- not acceptable for a 8 hour flight! your food really has declined crew great and I am loyal to delta

Boarding in Amsterdam is always chaotic. KLM/ Delta has not streamlined or made it efficient as it was boarding in Detroit . The food was mediocre The crew was unfriendly and more focused on getting things done quickly rather than service with a smile .

Internet on both flights was sketchy. Thus in flight entertainment was non- existent on MN - Balrimote leg.

Our flight was delayed for almost 2 hours resulting in a rush to connect to our next flight

It took 30 minutes to check in with the Westjet rep. They didn’t have enough seats and she needed to make a call… I am always “randomly” selected to be checked at security. Their “randomly “ selection system may need some updating. They treat people like criminals. It is not appropriate behavior.

Will never book through you again. Very disappointed in the notices and action taken or provided when planes are rescheduled, enough to cause missed connections

Lost my luggage. Filed a report and there is no response. Received a phone call from another airline that said they had the bag and they did not know what to do with it

Very good over all , would have been nice to have entertainment on the flight

Absolutely the worst airline I have ever taken. They lost my baggage and told me my bag tags had been cancelled. When my bags arrived days later I had to pick them up at 3:15 am. My return flight was delayed another 6 hours and they broke my bag. Westjet does nothing to try and make it a better customer experience and all the customers services representatives I spoke with were useless and incompetent. Never flying westjet again.

it's all good nothing you can do make better 😌

Very old planes. Seats were not comfortable. Air was not on during the flight leading to incredibly stuffy conditions.

It was so bad experience they wanted just charged passengers for any reason.

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.

flight was delayed 6 hours for weather, then cancelled because of the crash in toronto, but none of the links to cancel or rebook my flights are working

Ok Did not like that the second leg of flight was moved earlier making it a rush to make it

My flight was delayed, causing a shortened connection to my second flight, which led to a stressful experience. Additionally, I had to pay the luggage fee twice, for which I have receipts. Since Air Canada and United Airlines collaborate, their partnership should aim to provide better service, rather than leaving passengers to bear the consequences of an unprofessional experience.

Minimal food offered (crackers). Had to clean the seat with a wet wipe because of dried food.

Our flight was rescheduled causing us to miss our connecting flight, then missed our option of a ferry.

Not very comfortable when stuck in a middle with passengers that encroach on your personal space.

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

Information on your arrival and departure airports

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