ORD - YQR

$184 Find Cheap Flights from Chicago to Regina

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Regina departing on 9/5. 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 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
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Flights 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

Mon, Oct 6 - Sun, Oct 12
WestJet Logo
5:30 pm - 1:06 amORD-YQR
8h 36m1 stop
WestJet Logo
6:55 am - 4:43 pmYQR-ORD
8h 48m1 stop
$284WestJet
Find Deal
Thu, Nov 6 - Tue, Nov 11
Air Canada Logo
3:55 pm - 11:19 pmORD-YQR
7h 24m1 stop
Air Canada Logo
5:00 am - 1:01 pmYQR-ORD
8h 01m1 stop
$343Air Canada
Find Deal
Thu, Nov 6 - Tue, Nov 11
Air Canada Logo
3:55 pm - 11:19 pmORD-YQR
7h 24m1 stop
Air Canada Logo
5:00 am - 2:55 pmYQR-ORD
9h 55m2 stops
$348Air Canada
Find Deal
Mon, Oct 6 - Sun, Oct 12
WestJet Logo
5:30 pm - 11:01 pmORD-YQR
6h 31m1 stop
WestJet Logo
5:30 pm - 4:43 pmYQR-ORD
22h 13m2 stops
$401WestJet
Find Deal
Wed, Nov 12 - Wed, Nov 19
 Logo
7:25 am - 10:51 pmORD-YQR
15h 26m2 stops
 Logo
5:00 am - 6:55 pmYQR-ORD
13h 55m2 stops
Mon, Oct 6 - Sun, Oct 12
WestJet Logo
5:30 pm - 9:30 amORD-YQR
17h 00m2 stops
WestJet Logo
5:30 pm - 4:43 pmYQR-ORD
22h 13m2 stops
$464WestJet
Find Deal
Thu, Nov 6 - Tue, Nov 11
United Airlines Logo
7:25 am - 10:51 pmORD-YQR
15h 26m2 stops
United Airlines Logo
10:45 am - 11:36 amYQR-ORD
24h 51m2 stops
$488United Airlines
Find Deal
Wed, Nov 12 - Wed, Nov 19
 Logo
8:30 pm - 12:23 amORD-YQR
27h 53m3 stops
 Logo
7:05 am - 6:25 amYQR-ORD
23h 20m3 stops
Wed, Nov 12 - Wed, Nov 19
 Logo
7:35 am - 10:05 amORD-YQR
26h 30m2 stops
 Logo
7:05 am - 6:25 amYQR-ORD
23h 20m3 stops
Thu, Nov 6 - Tue, Nov 11
United Airlines Logo
8:50 am - 10:51 pmORD-YQR
14h 01m2 stops
United Airlines Logo
10:45 am - 11:36 amYQR-ORD
24h 51m2 stops
$510United Airlines
Find Deal
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.

What’s the cheapest day of the week to fly from Chicago to Regina?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Regina clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Regina on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Chicago to Regina. For your return ticket, we recommend flying on a Friday and avoiding Thursdays for the best deals.

Good to know

Cheapest flight$184
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 $184 for a one-way ticket and $284 for a round-trip.

  • 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 $311 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 8896 reviews
7.7Boarding
6.6Food
7.1Entertainment
7.3Comfort
8.1Crew
Airline reviews

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

10.0 ExcellentAnita, Jul 2025ORD - CMH
Read more United Airlines reviews

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

They cancelled and moved my flight with no email or text or any other notice. I discovered this only when I attempted to check in for my flight. Actual flying experience was above average.

They were on time and everything went as expected. The only thing that could be better was they didn't wait for us to get through customs to pick up our luggage off the carousel. An employee picked it up and was shoving it together with others onto a cart. Later we found one of our luggage was slightly bent.

Delayed boarding. Delayed taking off. Delayed landing. Missed our connecting flight. Our seats on this plane were not assigned until last minute, splitting up our family with kids. I sat in the last row next to the bathroom with so many people rubbing up against me to get to the bathroom the entire flight.

Another delayed flight. Then got bumped to a later connecting flight, over two hours later! Plane was hot and uncomfortable.

Asked to cancel flight 6 days in advance of flight back to St. Louis, MO. Would not allow. No credit either.

Crew was nice especially by North American standards. Bad good. No entertainment screens. Terrible WiFi

Not only was the flight delayed more than 3 hours but also there was no internet or movies on the flight. It was Flair/Spirit quality of experience at Westjet prices

West Jet flight was cancelled and I was not notified. I found out when I tried to check in on-line. Spent 4 hours on the phone with West Jet and Just Fly trying to figure what happened.

Only issue was checking in took over an hour and was very stressful. It all worked out, but we weren't sure for a while.

We didn’t make the flight due to Delta’s check in line moving too slow.

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

Information on your arrival and departure airports

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