YQR - ORD

C$ 157 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 14/11. 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

Wed, 29 Oct - Wed, 5 Nov
United Airlines Logo
9:45 a.m. - 8:58 p.m.YQR-ORD
10h 13m1 stop
United Airlines Logo
7:10 a.m. - 10:51 p.m.ORD-YQR
15h 41m1 stop
C$ 369United Airlines
Find Deal
Wed, 5 Nov - Fri, 14 Nov
Multiple Airlines Logo
10:45 a.m. - 8:58 p.m.YQR-ORD
10h 13m1 stop
Multiple Airlines Logo
8:15 p.m. - 10:39 a.m.ORD-YQR
14h 24m1 stop
C$ 397Multiple Airlines
Find Deal
Wed, 5 Nov - Fri, 14 Nov
Multiple Airlines Logo
10:45 a.m. - 10:50 p.m.YQR-ORD
12h 05m1 stop
Multiple Airlines Logo
12:50 p.m. - 10:39 a.m.ORD-YQR
21h 49m2 stops
C$ 404Multiple Airlines
Find Deal
Sun, 9 Nov - Wed, 12 Nov
Multiple Airlines Logo
11:45 a.m. - 5:08 p.m.YQR-ORD
5h 23m1 stop
Multiple Airlines Logo
6:25 p.m. - 11:51 p.m.ORD-YQR
29h 26m2 stops
C$ 419Multiple Airlines
Find Deal
Sun, 9 Nov - Wed, 12 Nov
Multiple Airlines Logo
11:45 a.m. - 10:45 a.m.YQR-ORD
23h 00m1 stop
Multiple Airlines Logo
7:58 p.m. - 11:51 p.m.ORD-YQR
27h 53m1 stop
C$ 429Multiple Airlines
Find Deal
Fri, 14 Nov - Fri, 21 Nov
Multiple Airlines Logo
2:10 p.m. - 11:06 p.m.YQR-ORD
32h 56m2 stops
Multiple Airlines Logo
5:20 p.m. - 6:17 p.m.ORD-YQR
24h 57m1 stop
C$ 443Multiple Airlines
Find Deal
Wed, 29 Oct - Wed, 5 Nov
Delta Logo
11:45 a.m. - 11:58 p.m.YQR-ORD
11h 13m2 stops
Delta Logo
8:57 a.m. - 6:17 p.m.ORD-YQR
9h 20m1 stop
C$ 477Delta
Find Deal
Fri, 14 Nov - Fri, 21 Nov
Multiple Airlines Logo
6:10 p.m. - 5:32 a.m.YQR-ORD
35h 22m3 stops
Multiple Airlines Logo
11:36 a.m. - 6:17 p.m.ORD-YQR
6h 41m1 stop
C$ 516Multiple Airlines
Find Deal
Sun, 9 Nov - Wed, 12 Nov
Multiple Airlines Logo
6:10 p.m. - 1:35 p.m.YQR-ORD
19h 25m2 stops
Multiple Airlines Logo
9:22 p.m. - 11:51 p.m.ORD-YQR
26h 29m2 stops
C$ 540Multiple Airlines
Find Deal
Wed, 5 Nov - Fri, 14 Nov
Multiple Airlines Logo
7:20 p.m. - 6:20 p.m.YQR-ORD
23h 00m3 stops
Multiple Airlines Logo
2:20 p.m. - 11:45 a.m.ORD-YQR
21h 25m1 stop
C$ 547Multiple Airlines
Find Deal

Everything you should know

Top airlines
United Airlines
Cheapest • from C$ 369 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 40% price drop
January
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
C$ 369
Typical prices: C$ 526-702
United Airlines
Wed 29/10Wed 5/11
YQR - ORD • 1 stop
Cheapest one-way flights
C$ 219
United Airlines
Fri 14/11
YQR - ORD • 1 stop
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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.

How much is a round-trip flight from Regina to Chicago O'Hare Intl Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Regina to Chicago O'Hare Intl Airport departing in October.

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 September, where tickets cost C$ 391 (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$ 1,625 and C$ 743 respectively.

Good to know

Low seasonJuly
Cheapest flightC$ 218
Best time to beat the crowds (16% less expensive on average)
Most popular time to fly and prices are also 1% 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$ 157 for a one-way ticket and C$ 265 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?

    SkyTeam, and Star Alliance are the airline alliances operating flights between Regina and Chicago, with SkyTeam 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$ 613 and an overall rating of 7.9, Delta is the most popular choice. WestJet is also a great choice for the route, with an average price of C$ 703 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.
7.9
DeltaOverall score based on 7961 reviews
7.9Entertainment
8.2Boarding
7.9Comfort
7.3Food
8.5Crew
Airline reviews

Movie selection was meh. Food was great. Crew as always great. I paid for premium because that’s the only way not to feel like a sardine. That’s how economy should be imo. Sadly passengers have to pay an extra $1000 to get what they should at base price but that’s all airlines. The airline industry in general treats passengers as cargo.

10.0 ExcellentAnonymous, Sep 2025LHR - MCO
Read more Delta reviews

Movie selection was meh. Food was great. Crew as always great. I paid for premium because that’s the only way not to feel like a sardine. That’s how economy should be imo. Sadly passengers have to pay an extra $1000 to get what they should at base price but that’s all airlines. The airline industry in general treats passengers as cargo.

Gate agent rushed to fill hot jetway with crowd so it took over 12 minutes to go from gate to plane. Just like a discount airline Pooly prepared cabin and third time that claim of rough air prevented any cabin service. Friends on a Southwest flight at similar time had service.

My only complaint on any flight is meals but your gnocchi was good. The worst is breakfast. I can’t understand why you don’t just serve something simple like yogurt, fruit and a muffin or cinnamon roll.

Cramped seating for me. Luckily it wasn’t a long flight

The crew was very nice and very attentive. However, I was surprised to find that they did not carry small throw-up bags. I got sick from the turbulence and they had to bring me a trash bag.😳 You can imagine how embarrassing is to lift a large trash bag with vomit over somebody else's head. Just bring this small discreet little bags back to the regular supply for the seats. Otherwise, I love Delta airlines.

Lounge in Lagos is terrible, food on board from Lagos to Atlanta was horrible. Only bright spot the cabin crew were awesome.

Awful. Flight from Cape Town was cancelled, rebooked for another day through Johannesburg, was downgraded to economy

The staff and the boarding procedure were all amazing . The one flight was not equipped with WIFI which now adays seems odd. All in all the experience was good

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

What do you expect from a Dash 8 plane? No seats really comfortable.

The snacks could have been better, and maybe some warm drinks instead of just water cause it was very very cold.

Do not fly on WestJet if you have a connection. It failed to integrate with my connecting Delta flight and I almost missed it.

There was a man who was very rude at boarding. On the other hand personal bag measuring box is too small compared to USA airlines,

A little better seat cushions would be appreciated. Crews were all good.

The process and flight were both smooth and trouble free

Flight delayed 3 hours, missed my connection in Atlanta. Instead of getting to Savannah at 6PM arrived after 10:00PM Middle seat, couldn't get isle or window, couldn't book my seats in advance, had to book at the gate. That's a 1st for me and I used to travel a lot

my carry-on bag was delayed and I did not receive it until the day of my return at the airport. This delay caused me significant inconvenience, as I did not have access to my personal belongings for the duration of my trip. I had expected to rely on my carry-on items, and being without them negatively impacted my travel experience.

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 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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