ORD - YQR

$270 Find Cheap Flights from Chicago to Regina

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Regina departing on 1/22. 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 Regina

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Regina, 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 Chicago to Regina, as well as popular online travel agencies
Travelers love KAYAK
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Everything you should know

Cheapest round-trip
$270
Air Canada
Thu 1/22Mon 1/26
ORD - YQR • 1 stop
Cheapest one-way
Multiple Airlines
Sun 1/11
ORD - YQR • multi-stop
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We hope you love your trip to Regina!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Regina (ORD-YQR)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Regina 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 Chicago to Regina

Thu, Jan 22 - Mon, Jan 26
Air Canada Logo
3:55 pm - 11:19 pm
ORD
-
YQR
7h 24m1 stop
Air Canada Logo
5:00 am - 7:45 pm
YQR
-
ORD
14h 45m1 stop
$270Air Canada
Thu, Jan 22 - Mon, Jan 26
Air Canada Logo
3:55 pm - 11:19 pm
ORD
-
YQR
7h 24m1 stop
Air Canada Logo
5:00 am - 8:10 pm
YQR
-
ORD
15h 10m2 stops
$279Air Canada
Mon, Mar 2 - Sat, Mar 7
Air Canada Logo
8:40 pm - 10:39 am
ORD
-
YQR
13h 59m1 stop
Air Canada Logo
5:00 am - 1:01 pm
YQR
-
ORD
8h 01m1 stop
$280Air Canada
Mon, Apr 6 - Thu, Apr 9
Air Canada Logo
8:20 pm - 9:32 am
ORD
-
YQR
14h 12m1 stop
Air Canada Logo
5:00 am - 1:00 pm
YQR
-
ORD
7h 00m1 stop
$281Air Canada
Fri, Jun 19 - Sun, Jun 21
WestJet Logo
5:30 pm - 1:07 am
ORD
-
YQR
8h 37m1 stop
WestJet Logo
5:30 pm - 4:43 pm
YQR
-
ORD
46h 13m2 stops
$307WestJet
Fri, Jun 19 - Sun, Jun 21
WestJet Logo
5:30 pm - 1:07 am
ORD
-
YQR
8h 37m1 stop
WestJet Logo
5:30 pm - 4:43 pm
YQR
-
ORD
46h 13m2 stops
$308WestJet
Thu, Jan 22 - Mon, Jan 26
Air Canada Logo
3:35 pm - 10:39 am
ORD
-
YQR
19h 04m2 stops
Air Canada Logo
5:00 am - 8:10 pm
YQR
-
ORD
15h 10m2 stops
$312Air Canada
Fri, Jun 19 - Sun, Jun 21
Air Canada Logo
9:50 am - 7:10 pm
ORD
-
YQR
10h 20m1 stop
Air Canada Logo
8:10 pm - 9:00 am
YQR
-
ORD
11h 50m1 stop
$316Air Canada
Fri, Jun 19 - Sun, Jun 21
WestJet Logo
5:30 pm - 9:30 am
ORD
-
YQR
17h 00m2 stops
WestJet Logo
5:30 pm - 4:43 pm
YQR
-
ORD
46h 13m2 stops
$323WestJet
Fri, Jun 19 - Sun, Jun 21
WestJet Logo
5:30 pm - 9:30 am
ORD
-
YQR
17h 00m2 stops
WestJet Logo
5:30 pm - 4:43 pm
YQR
-
ORD
46h 13m2 stops
$324WestJet
Booking Insights

KAYAK's insights & trends for Chicago to Regina flights

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

Which airlines fly non-stop between Chicago O'Hare Intl Airport and Regina?

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

There are 2 airlines that fly nonstop from Chicago O'Hare Intl Airport to Regina. They are United Airlines and WestJet. The cheapest airline for this route is United Airlines, with the best round-trip deal found costing $284. On average, the best prices for this route can be found at United Airlines.

Good to know

Cheapest flight$270
Flight from Chicago to Regina

When to book flights from Chicago to Regina

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

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

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Regina was $270 for a round-trip ticket.

  • Do I need a passport to fly between Chicago and Regina?

    A passport is required to fly from Chicago to Regina.

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

    On your way to Regina, you’ll fly out from Chicago O'Hare Intl. You’ll be landing at Regina.

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

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

  • Which airline alliances offer flights from Chicago to Regina?

    Star Alliance is the only airline alliance operating flights between Chicago and Regina.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Regina are United Airlines and WestJet. With an average price for the route of $336 and an overall rating of 7.4, United Airlines is the most popular choice. WestJet is also a great choice for the route, with an average price of $373 and an overall rating of 7.2.

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

    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 Chicago to Regina.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Regina from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Regina?

    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 Regina with an airline and back to Chicago with another airline. Booking your flights between Chicago and YQR can sometimes prove cheaper using this method.

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

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

Reviews of the top airlines flying from Chicago to Regina

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Regina. 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 Chicago to Regina? 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.
7.4
United AirlinesOverall score based on 9145 reviews
8.1Crew
7.3Comfort
7.1Entertainment
7.7Boarding
6.6Food
Airline reviews

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

6.0 GoodPatricia, Jan 2026
ORD - LAS
Read more United Airlines reviews

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Plane seating was uncomfortable, very tight fitting for someone my height, did not recline and overall un enjoyable

Everything was good except for flight delay, but it was because of the snow storm in the arrival airport.

No communication from Kayak or West Jet. Booked extra flights, flights cancelled, no one answers calls. Will be disputing charges.

The trip from LAX to Calgary was aboard a 737-700, which is more than twenty years old. Service was fine, and the food was good, but there was no inflight entertainment, and no WiFi. The flight from Calgary to Vancouver was also delayed more than an hour, due to congestion on the Calgary tarmac. And no food service, but there was in-flight WiFi which made a big difference.

Leg room is a problem the plane was dirty and there were no movies available on the app

The personal item sizer cannot take a standard backpack, and the cabin luggage sizer cannot take a standard carry-on. Designed for people from the island of Lilliput!!. and also compels people to pay additional fees to check their bags. Making money by ticking off the passengers is a very short-sighted business strategy, especially since they have a choice of carriers

my wife got very sick and we did not travel . we booked and bought the travel insurance and dot nothing but hassle and a triangle of stress in trying to make the insurance claim I called in and was told they would not give me anything in writing to say they would not refund my money back this make it impossible to file the claim I will never book with Kayak again.

We got delayed to the point of having a 20 hour layover. That is absurd. I couldn’t believe it. I’m furious.

Kayak was the problem! The tickets we bought did not allow for carry on or checked luggage and we ended up paying more for those services than the tickets! The paperwork Kayak provided for the receipt left the luggage policy for Westair intentionally blank. This was intentionally decietful on Kayak's part. Our additional cost was over $400.00! I will be calling customer service today asking for refunds and I will keep you informed on any review sites as I can. Keith

Leaving the same day as planned would've been better

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

Information on your arrival and departure airports