ORD - YQR

$103 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 8/15. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

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

Bundle and saveSave money when you bundle your flight + hotel.

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

Flights Deals
Useful Info
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

Wed, Jul 30 - Wed, Aug 6
WestJet Logo
5:30 pm - 1:07 amORD-YQR
8h 37m1 stop
WestJet Logo
2:05 pm - 4:44 pmYQR-ORD
25h 39m1 stop
$273WestJet
Find Deal
Wed, Jul 30 - Wed, Aug 6
WestJet Logo
5:30 pm - 11:02 pmORD-YQR
6h 32m1 stop
WestJet Logo
2:05 pm - 4:44 pmYQR-ORD
25h 39m1 stop
$288WestJet
Find Deal
Wed, Jul 30 - Wed, Aug 6
WestJet Logo
5:30 pm - 1:07 amORD-YQR
8h 37m1 stop
WestJet Logo
8:35 pm - 4:44 pmYQR-ORD
19h 09m1 stop
$300WestJet
Find Deal
Wed, Jul 30 - Wed, Aug 6
WestJet Logo
5:30 pm - 1:07 amORD-YQR
8h 37m1 stop
WestJet Logo
8:40 pm - 4:44 pmYQR-ORD
19h 04m1 stop
$301WestJet
Find Deal
Tue, Jul 29 - Tue, Aug 5
 Logo
5:30 pm - 1:07 amORD-YQR
8h 37m1 stop
 Logo
7:00 am - 3:04 pmYQR-ORD
7h 04m1 stop
Tue, Jul 29 - Tue, Aug 5
WestJet Logo
5:30 pm - 1:07 amORD-YQR
8h 37m1 stop
WestJet Logo
5:30 pm - 12:39 pmYQR-ORD
18h 09m1 stop
$319WestJet
Find Deal
Tue, Jul 29 - Tue, Aug 5
 Logo
5:30 pm - 2:43 pmORD-YQR
22h 13m1 stop
 Logo
8:35 pm - 9:09 amYQR-ORD
11h 34m2 stops
Thu, Nov 6 - Tue, Nov 11
United Airlines Logo
7:10 am - 10:36 pmORD-YQR
15h 26m1 stop
United Airlines Logo
10:45 am - 8:58 pmYQR-ORD
10h 13m1 stop
$383United Airlines
Find Deal
Thu, Nov 6 - Tue, Nov 11
Air Canada Logo
9:50 am - 11:18 pmORD-YQR
13h 28m1 stop
Air Canada Logo
6:00 am - 8:25 pmYQR-ORD
14h 25m2 stops
$411Air Canada
Find Deal
Thu, Nov 6 - Tue, Nov 11
United Airlines Logo
8:50 am - 11:18 pmORD-YQR
14h 28m2 stops
United Airlines Logo
10:45 am - 8:10 pmYQR-ORD
9h 25m2 stops
$656United Airlines
Find Deal
Useful Info

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, Thursday 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$103
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 $103 for a one-way ticket and $273 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, and SkyTeam are the airline alliances operating flights between Chicago and Regina, with Star Alliance being the most commonly used for this route.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Regina are Delta and United Airlines. With an average price for the route of $617 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $311 and an overall rating of 7.4.

  • 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.

Top 4 airlines serving 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.
8.0
DeltaOverall score based on 7963 reviews
7.9Entertainment
7.9Comfort
7.3Food
8.2Boarding
8.5Crew
Airline reviews

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

4.0 OkayKoonj, Jun 2025MSP - AUS
Read more Delta reviews

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Overall, aside from the baggage issue, it was as good as one expects.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

I want to single out flight attendant Mitch who was in the Premium Economy section. When my wife’s hearing aide dropped through the cushion under the seat he was able to locate it and return it to her. Food was a different matter. Dinner was fine. Breakfast was another matter. They had a yogurt dish that the ran out of and the alternative was not very good according to those we talked to.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Flight was delayed long enough that I was misding my connecting flight. The agents could not get me on a comparable flight, nor could they get me s Main Cabin seat I had paid for, nor could they get me on a comparable connecting flight. The gate agent would not issue meal vouchers, even though I was delayed over six hours! I had to spend over an hour and 15 minutes with customer service on the phone to See if they could get me on a better flight and get a meal voucher. Customer service was not helpful enough in trying to find alternate flights and it Ended up taking me 24 hours for a 12 hour trip!! Delta does not provide upgrades NOR will they even give you a pass for a few hours to their lounge. They claim that they do not issue daily passes to their lounge anymore. I call BS since this would be no extra cost to them to provide excellent customer service and give you a few hours to relax in comfort when you’re sitting in a crowded airport and your flight has been screwed up for that many hours.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

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.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

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.

The flight was ahead of schedule. A half glass of juice and a cookie is pathetic! No entertainment possibilities. Not even a plug-in for phone or IPad if you wanted to watch a downloaded movie. Back to flying Air Canada!

The flight was ahead of schedule. A half glass of juice and a cookie is pathetic!

The staff were the friendliest I have encountered in years. Absolutely great!

Plane changed to one with no entertainment system or ability to serve hot meals

Flight was delayed 3 times. Then cancelled due to pilot being timed out. They refused hotel vouchers. Gate attendants were very rude and could not help you at all.

Good. Would be better if the carry on baggage was free.

Flight was delayed but the real issue is how long we sat after boarding. Space very limited for an overnight flight and seatbacks didn’t recline so it was almost impossible to sleep.

The staff made sure I was comfortable, moved me to a better seat with more leg room

Miserable staff as it was a late/delayed flight and crew wasn’t in the best spirits. Completely understood as neither was most of the passengers. Still unacceptable l.

It was a short flight, and no entertainment. That was not a problem for us, but there is no option for "not applicable". There was a bit of turbulence, so there was no food service.

All was good except for the seats, not very comfy.

2.5 hour delay sitting in the plane on the tarmac, you tell me how the experience was

This flight didn't happen for me because of overbooking.

Everything was simple and easy. The lady at the gate was super friendly, I wish I had her name to share. She's a little older, dark-haired. You can tell she likes her job and would be a great influence on any young people training with her.

Crammed in like cattle waited 30 mins for late connecting flight (flight didn’t wait for me for me when I missed my connection at 2 different airports on outward journey)

Short delay to Regina from Toronto. No in flight entertainment, but crew were professional in their duties

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.