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YQR - ORD

Find cheap flights from Regina to Chicago from C$ 231

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 7/6. 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
0 bags
sam. 8/6
sam. 15/6

Search hundreds of travel sites at once for deals on flights to Chicago

 
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
In the last 7 days, travellers have searched 43,968,530 times on KAYAK, and here is why:

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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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:15 a.m. - 11:58 p.m.YQR-ORD
14h 43m2 stops
9:36 a.m. - 2:28 p.m.ORD-YQR
5h 52m1 stop
C$ 466Delta
Find Deal
sam., 25 mai - mer., 29 mai
7:35 p.m. - 10:01 a.m.YQR-ORD
13h 26m2 stops
9:00 a.m. - 2:25 p.m.ORD-YQR
6h 25m1 stop
C$ 469Air Canada
Find Deal
sam., 25 mai - mer., 29 mai
3:05 p.m. - 5:20 a.m.YQR-ORD
13h 15m2 stops
9:25 p.m. - 2:28 p.m.ORD-YQR
18h 03m2 stops
C$ 478
Find Deal
sam., 25 mai - mer., 29 mai
8:15 a.m. - 8:55 p.m.YQR-ORD
11h 40m2 stops
3:50 p.m. - 2:28 p.m.ORD-YQR
23h 38m1 stop
C$ 482Delta
Find Deal
sam., 25 mai - mer., 29 mai
3:05 p.m. - 7:03 p.m.YQR-ORD
26h 58m3 stops
9:25 p.m. - 2:28 p.m.ORD-YQR
18h 03m2 stops
C$ 493
Find Deal
sam., 25 mai - mer., 29 mai
3:05 p.m. - 7:03 p.m.YQR-ORD
26h 58m3 stops
10:58 a.m. - 2:28 p.m.ORD-YQR
28h 30m3 stops
C$ 522
Find Deal
sam., 25 mai - mer., 29 mai
3:05 p.m. - 5:20 a.m.YQR-ORD
13h 15m2 stops
10:52 p.m. - 12:56 a.m.ORD-YQR
27h 04m3 stops
C$ 543
Find Deal
sam., 25 mai - mar., 28 mai
6:00 a.m. - 7:22 a.m.YQR-ORD
24h 22m2 stops
6:00 a.m. - 2:28 p.m.ORD-YQR
9h 28m1 stop
C$ 556Delta
Find Deal
jeu., 15 août - lun., 19 août
3:05 p.m. - 7:03 p.m.YQR-ORD
26h 58m3 stops
10:52 p.m. - 12:56 a.m.ORD-YQR
27h 04m3 stops
C$ 558
Find Deal
sam., 25 mai - mar., 28 mai
6:15 a.m. - 8:36 p.m.YQR-ORD
13h 21m2 stops
3:50 p.m. - 12:57 a.m.ORD-YQR
10h 07m2 stops
C$ 797WestJet
Find Deal
jeu., 15 août - lun., 19 août

Flights from Regina to Chicago - Travel Insights & Trends

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 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 January, where tickets cost C$ 289 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is C$ 1,098 and C$ 965 respectively.

Which airlines provide the cheapest flights from Regina to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Regina to Chicago found by KAYAK users in the last 72 hours was for C$ 466 on Delta, followed by Air Canada (C$ 469). One-way flight deals have also been found from as low as C$ 267 on Delta and from C$ 290 on Air Canada.

Good to know

Low season

September

High season

February

Cheapest flight

C$ 231
Best time to beat the crowds (8% less expensive on average)
Most popular time to fly and prices are also 36% 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$ 168 for a one-way ticket and C$ 339 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, WestJet or Air Canada?

    The two airlines most popular with KAYAK users for flights from Regina to Chicago are WestJet and Air Canada. With an average price for the route of C$ 758 and an overall rating of 7.5, WestJet is the most popular choice. Air Canada is also a great choice for the route, with an average price of C$ 634 and an overall rating of 7.0.

  • 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 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.
7.5
WestJetOverall score based on 2942 reviews
6.5Entertainment
7.3Comfort
6.5Food
7.7Boarding
8.2Crew
Airline reviews

Airport monitors did not give the gate for our flight returning Detroit to Vancouver Juice served from glass storage containers are a far more healthy alternative for people. And would also minimize the need for recycling plastic or aluminum containers

2.0 MediocreAnonymous, Apr. 2024YVR - MSP
Read more about WestJet reviews

Airport monitors did not give the gate for our flight returning Detroit to Vancouver Juice served from glass storage containers are a far more healthy alternative for people. And would also minimize the need for recycling plastic or aluminum containers

I wish that seats closer to the front of the plan were available, but when I booked the flight the seats were VERY expensive so I did not book seats at that time. The day before flying only seats at the back of the plane were available. It takes so long to board the plane and empty the plane on arrival due to SO many roller bags.

Good flight. No I’m seat entertainment. But my phone worked just fine on the west jet app.

I had planned to watch the Westjet entertainment for the entire flight however, because the seat mounted outlets in our row did not work.

Not a bad flight but our priority tagged luggage was the very last to come down the carousel.

Plane had a flat tire, delayed boarding and takeoff but one in the air, smooth. Make sure you have downloaded the WJ app before you leave. When on board, you can watch movies or TV shows offered on the app, it passed the time very quickly.

The online check-in process was not smooth. I encountered error messages while trying to add baggage, and the payment was processed twice. The refund process has also been challenging, and I still haven't received the refund.

Our recent flight from edmontown to kahalui was excellent. The service staff was very friendly, knowledgeable, funny and attentive. Thanks to all involved that made or travel such a pleasant experience and we hope to fly with west jet again soon

The flight was delayed and I missed boarding my 7 day cruise. I had to book a separate flight home

No real issues just wasnt able to hear / understand any announcements flight attendant was making but everything else was really good- ended up checking my carry on case for free which made deboarding quicker. I would fly West Jet for all my flights.

Everything was great. I really like how they had their safety film set up showing you the beauty of the country.

I liked the early check in. Flight was a bit bumpy due yo weather. Overall, everything went well.

Limited snack options cause the snack vendor was on strike

The experience was generally above average. The only downside was the absence of WiFi during my flight from Vancouver to San Francisco.

on demand entertainment in seat back awesome Check in Kiosk too demanding with endless demand for more information information then says go to counter. Counter agent unfriendly. Do it yourself check in luggage procedure not intuitive, upset employees frustrated the whole procedure.

It was an excellent experience, traveling from Toronto to Denver with United.

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

Flight was delayed, I had to put my luggage all the way in the back! They served only a beverage no snack on the way in Air Canada, definitely not a good first impression.

Headphones for the movies have too much bass and can't be adjusted. Almost impossible to hear. Great movie selections but can't really watch them because you can't hear them. Also the system is very slow.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

Book cheap flights from Regina to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Regina to Chicago found on KAYAK in the last 72 hours.
7/6ven.
1 stop
9h 51mYQR-ORD
C$ 231
6/6jeu.
1 stop
8h 20mYQR-ORD
C$ 253
7/6ven.
2 stopsDelta
14h 41mYQR-ORD
C$ 267
8/6sam.
2 stopsDelta
9h 48mYQR-ORD
C$ 275
6/6jeu.
3 stops
35h 51mYQR-ORD
C$ 278
8/6sam.
1 stopAir Canada
13h 51mYQR-ORD
C$ 290
8/6sam.
3 stops
21h 55mYQR-ORD
C$ 293
6/6jeu.
2 stops
17h 25mYQR-ORD
C$ 302
7/6ven.
3 stops
15h 40mYQR-ORD
C$ 357
7/6ven.
3 stops
15h 40mYQR-ORD
C$ 360

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Regina - Chicago Flights

Departure:

Regina (undefined)Canada

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - Regina

Cabin classes: