YQR - ORD

C$ 210 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 29/12. 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
1 adult, Economy, 0 bags

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
Travellers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
C$ 376
Typical prices: C$ 556-C$ 733
WestJet
Thu 16/4Wed 17/6
YQR - ORD • 1 stop
Cheapest one-way flights
C$ 210
Multiple Airlines
Mon 29/12
YQR - ORD • 1 stop
Top airlines
WestJet
Cheapest • from C$ 376 (round-trip)
Air Canada
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
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

Thu, 16 Apr - Wed, 17 Jun
WestJet Logo
3:25 p.m. - 1:35 p.m.YQR-ORD
21h 10m1 stop
WestJet Logo
5:30 p.m. - 1:07 a.m.ORD-YQR
8h 37m1 stop
C$ 376WestJet
Find Deal
Thu, 16 Apr - Wed, 17 Jun
WestJet Logo
5:10 p.m. - 1:35 p.m.YQR-ORD
19h 25m2 stops
WestJet Logo
5:30 p.m. - 11:02 p.m.ORD-YQR
6h 32m1 stop
C$ 408WestJet
Find Deal
Mon, 15 Dec - Mon, 22 Dec
Multiple Airlines Logo
6:10 a.m. - 1:35 p.m.YQR-ORD
7h 25m1 stop
Multiple Airlines Logo
7:38 p.m. - 6:20 p.m.ORD-YQR
22h 42m1 stop
C$ 450Multiple Airlines
Find Deal
Sun, 3 May - Mon, 4 May
Delta Logo
6:55 a.m. - 4:43 p.m.YQR-ORD
8h 48m1 stop
Delta Logo
5:30 p.m. - 1:07 a.m.ORD-YQR
8h 37m1 stop
C$ 482Delta
Find Deal
Sun, 3 May - Mon, 4 May
Delta Logo
6:55 a.m. - 4:43 p.m.YQR-ORD
8h 48m1 stop
Delta Logo
5:30 p.m. - 11:02 p.m.ORD-YQR
6h 32m1 stop
C$ 484Delta
Find Deal
Sun, 3 May - Mon, 4 May
Air Canada Logo
7:15 p.m. - 9:54 a.m.YQR-ORD
13h 39m2 stops
Air Canada Logo
3:40 p.m. - 9:33 a.m.ORD-YQR
18h 53m2 stops
C$ 498Air Canada
Find Deal
Sun, 3 May - Mon, 4 May
Air Canada Logo
7:15 p.m. - 9:54 a.m.YQR-ORD
13h 39m2 stops
Air Canada Logo
8:25 p.m. - 9:33 a.m.ORD-YQR
14h 08m1 stop
C$ 501Air Canada
Find Deal
Sun, 3 May - Mon, 4 May
Air Canada Logo
7:15 p.m. - 9:54 a.m.YQR-ORD
13h 39m2 stops
Air Canada Logo
8:25 p.m. - 9:33 a.m.ORD-YQR
14h 08m1 stop
C$ 502Air Canada
Find Deal
Mon, 15 Dec - Mon, 22 Dec
Multiple Airlines Logo
10:40 a.m. - 6:05 a.m.YQR-ORD
19h 25m2 stops
Multiple Airlines Logo
7:38 p.m. - 6:20 p.m.ORD-YQR
22h 42m1 stop
C$ 513Multiple Airlines
Find Deal
Thu, 16 Apr - Wed, 17 Jun
Multiple Airlines Logo
3:25 p.m. - 6:27 p.m.YQR-ORD
26h 02m3 stops
Multiple Airlines Logo
5:30 p.m. - 11:02 p.m.ORD-YQR
6h 32m1 stop
C$ 547Multiple Airlines
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.

Which airlines provide the cheapest flights from Regina to Chicago?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Regina to Chicago were found on WestJet (C$ 376) and Delta (C$ 482).

Which airlines fly direct between Regina and Chicago O'Hare Intl Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Regina to Chicago O'Hare Intl Airport.

There is just one airline that flies from Regina to Chicago O'Hare Intl Airport direct and that is Air Canada. The best round-trip deal found from Air Canada for the route is C$ 412.

Good to know

Low seasonSeptember
Cheapest flightC$ 210
Best time to beat the crowds (49% less expensive on average)
Most popular time to fly (124% more expensive 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$ 376 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 is the only airline alliance operating flights between Regina and Chicago.

  • 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 airline 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.
7.1
Air CanadaOverall score based on 10456 reviews
7.1Comfort
7.8Crew
6.8Entertainment
7.3Boarding
6.3Food
Airline reviews

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

8.0 ExcellentGlenda, Jul 2025YXE - YYZ
Read more Air Canada reviews

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