ORD - YQR

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ORD — YQR
25 Jan — 1 Feb1
Return
1 adult
Economy
0 bags
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Tue 25/1
Tue 1/2

When to book flights from Chicago to Regina

Estimated round-trip price
Average price per month
Flight prices as travel date approaches

Top tips for finding a cheap flight

  • Morning departure is around 56% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking Chicago to Regina flights

Top airlines flying Chicago O'Hare Intl to Regina

Scores according to KAYAK customer reviews
7.9
DeltaOverall score based on 30305 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.5Food
Airline reviews

They made us check carry ons despite the entire aircraft overhead space being empty

Read more about Delta

They made us check carry ons despite the entire aircraft overhead space being empty

Cons: "We arrived around 39 minutes early and the whole process was very smooth"
Pros: "Crew was friendly, seats really comfortable!"
Cons: "Headphones sold for $ 2. Headphones preferably free"
Pros: "Crew was attentive and accommodating."
Cons: "Gates switched 3 times and all bags had to be checked because of a small aging plane."
Pros: "Calm and safe, just like I like it."
Pros: "Short lines"
Cons: "Seating arrangements"
Cons: "The carrots were hard and the bread was cold."
Pros: "Comfortable plane due to few passengers"
Cons: "7 hour delay after flight postponed."
Cons: "I would ask that the gate does not share in detail reason for delay in seat assignment is related to getting a family sitting together when the basic rules should apply unilaterally."
Pros: "Got to my destination without any issues"
Cons: "Seats/seating area are too small, and I'm not a big person."
Pros: "All good."
Cons: "Price"
Pros: "The flight was on time, the crew was pleasant and looked like they enjoyed working in the air."
Cons: "Our second time on a 787 Dreamliner across the Atlantic as about the same as the the first. The seat pitch is very tight so when a passenger reclines into the next row the seatback nearly touches your face. The Dreamliner seats seem to be very hard and it's difficult to get comfortable."
Cons: "No AC for an hour before takeoff - very uncomfortable. Audio for tv did not work."
Pros: "Son got wings, so was happy."
Cons: "No entertainment."
Cons: "Seat assignment for me and my traveling companion was done at gate. We had to sit in 2 different rows."
Pros: "Crew was nice and welcoming"
Cons: "Well, if our plane had been leaving on time it would've been superb."
Cons: "Notify the delay quickly"
Pros: "Helpful"
Cons: "More print media to read on"
Pros: "Crew was great."
Cons: "Couldn’t hear/understand the pilot"
Pros: "Flight attendant in first class was amazing."
Pros: "The boarding was fast and very well handled."
Cons: "It was delayed"
Pros: "N/A"
Cons: "Chinese Eastern did not try to help and solve my problem."
Pros: "There was a bit of a mixup in boarding the plane but otherwise the flight was good. There was no entertainment system on this short flight. The flight attendants were very pleasant & efficient. They only served snacks on this short flight but were very good at ensuring everyone had at least one or more beverages. The premium seats were very comfortable ."
Pros: "Short flight"
Cons: "Flight attendant was not willing to go above and beyond as he stated he would. My husband asked for a coke and the flight attendant told him he could only get water."
Pros: "It was a smooth boarding, flight and exit out of the plane."
Pros: "Snacks, cleanliness and crew"
Cons: "N/A"
Pros: "Nothing"
Cons: "They take them forever to find me another fly ,make miss my other fly, my work my time and my sleep"
Cons: "Entertainment app from Go Go didn’t Work."
Pros: "It was a normal flight as well expected."
Pros: "I was with my friend"
Cons: "Delayed 12+ hours"
Pros: "We had a 2 1/2 delay due to mechanical issues but the crews, flight and ground, did a great job. Thanks."
Pros: "Staff were friendly and boarding was and getting off was easy because flight was super empty. Timeliness was appreciated too."
Cons: "Seats don't recline far enough."
Pros: "I was given a complimentary upgrade."
Cons: "It takes time and worries to find the air train and Aeroflot registration."
Pros: "My flight was great. Boarding was easy and the seats were comfortable."
Pros: "I needed to run real fast to the connection flight and gladly got there on time."
Pros: "The service was amazing , the staff was honestly friendly and nice"
Pros: "Great service, nice agent friendly"
Pros: "Very friendly and professional gate agent and flight attendant"
Cons: "I was unable to fly at all due to a spelling error on my ticket. The airline refused to alter the ticket. Worst experience of my life, ruined my Christmas"
Pros: "Very nice flight and attentive staff. Enjoyed the view of NYC as we flew up the East River, then looped over Nassau County to approach LGA."
Cons: "The male flight attendant who handed out the complimentary drinks and snacks acted a bit strangely. I was very thirsty, and I asked him if I could keep the rest of the can of soda. He neither said yes nor no, but rather completely ignored what I said and just poured my drink and moved on. I was a mildly annoyed, but figured maybe it was policy and he was shy and didn't want to debate the matter. When he took care of the older couple behind us, however, things got really strange. He asked them whether they wanted pretzels or peanuts, but they misheard him and asked for a ginger ale. I happened to know that he did have ginger ale, since my wife had just gotten one, but rather than just pouring the old folks a drink, he repeated himself. "Peanuts or pretzels?" They misheard again and asked him whether he had a diet ginger ale. Again, rather than just pour them the drink, he repeated himself. "Peanuts or pretzels?" This went round and round a few more times -- like a poorly designed computer UI that refuses to accept anything except the correct input -- before the old couple finally figured out the disconnect and picked their snacks before their drinks. Very weird."
Pros: "Nothing"
Cons: "Cancelled my flight because I lost one of the arms"
Cons: "Layover"
Pros: "Short flight"
Cons: "Too cold Not friendly boarding agent"
Pros: "N/A"
Cons: "2.5 hour delay for no apparent reason at first (supposed mechanical issues with plane) and then waited on plane at gate for a missing pilot who never got picked up from his airport and got stuck in Chicago traffic trying to get to O'Hare. Eventually had to take pilot from another flight before leaving at 8:45 when flight was scheduled for 6:00am."
Cons: "Had a death in the family and no one would help me get back home"
Cons: "Plane was sat broken at gate and needed part to be flown in. 150 minutes delayed. Not acceptable."
Cons: "One hour late after a stay over already 4 hours."
Cons: "I am a 5'3" 125# woman who, unfortunately, had a middle seat assignment. The passenger to my right, on the aisle, weighed approximately 375# and took up 1/3 of my seat. The arm was not able to go down comfortably, and when it did it was not usable . The passenger on my left, window seat, was probably 6'7" and had to sit with a man spread in order to fit. I could not move and was extremely uncomfortable. The plane was overbooked so I was unable to move. Therefore, worst flight ever. Plus, I paid for a full seat and was only able to occupy half of it."
Cons: "They loose my luggage!!!!!!"
Pros: "Staff put in awful position to deal with upset clients Dealt with it as best as can be expected."
Cons: "Every time we have travelled from Chicago to Toronto, the flight gets cancelled. Had to leave 0230 to get to airport only to find that flight at 0800 was cancelled. Ugh!"
Pros: "Seating is more spacious then most"
Cons: "Customa in yul is a bit of a hassle, but not that bad."
Pros: "There wasn't anything that stood out that I could say I liked."
Cons: "I didn't care for the attitudes if the stage working in the Toronto airport. Things really aren't clear there for first-timers and much of the staff was acting like I should already know to do a lot of things when there weren't any clearly posted signs saying so. There is also a huge lack of organization."
Pros: "I got upgraded to first class!"
Pros: "N A"
Cons: "price online when i booked the ticket was different. Air Canada charged me extra for seating as well which was showing free at the time of booking Some thing is not right. Extta charges of $16 does not sounds good specially when its not disclosed."
Pros: "Very short flight, not much to say"
Cons: "The flight was delayed twice causing us to miss our connecting flight to Copenhagen. Air Canada then put us on a flight to London and then connecting to Copenhagen we arrived at 4 PM instead of 10AM ."
Cons: "They airline cancelled our return flight and booked us on another flight more than 2 hours later. We had an event to attend that night so we asked if they could book us on United so we wouldn't miss it. The agent outright lied and said there were no other United flights before then. As we were waiting for our flight, we heard the agents call the final call for a flight to Chicago. Truly disgusted with Air Canada - will never fly them again!"
Pros: "Extremely helpful and accommodating! Thanks to all!"
Cons: "Departure was late, causing me to have to run to the next gate"
Cons: "We were walking towards our seats near the end of the aircraft when this flight attendant stopped us from loading our hand luggage in the overhead bins. She made us stuff them under the seats in front of us. There was space im the overhead bin, but there was a bunch of stuff that belonged to the cabin crew. Rude."
Cons: "See above."
Pros: "The pilot seemed good and the staff on the plane were nice overall"
Cons: "Customer service from the group staff that checked us in was horrendous... (Lisa from Chicago ). We were not aware one of us needed eTA to fly through Canada and the agent was so belittling, rude and plane wrong with her information, that if it had not for our smarts, we might have not made it to our destination. I do not spend so much money to fly with an airline, whose agents treat it me like this! She really should be fired for her terrible manners and for giving customers wrong information..the second supervisor we talked to helped us, but the impression we got from the agent was so terrible, that it was hard to feel any good...no food on a flight during lunch hour, seems unfitting."
Cons: "My original flight was delayed by 3 hours, causing me to miss my connecting flight. Instead of arriving at 9:30 at my final destination I arrived at 1:30 am. Exhausted."
Pros: "I am sad to say I have little positive things to say about this experience."
Cons: "To begin, our flight was delayed an hour into Toronto. We asked the flight attendant about our connecting flight and they said they would find an answer. It ended up that we landed just as the flight was scheduled to leave. Why they could delay pur flight but would not hold another flight by 20 minutes is very questionable. Then we got to customer service, the rep told us that we could only get on the next flight going out tomorrow at the same time which meant 24 hours lost. Of our vacation- which hotels already booked and tours already booked. When I asked if there was anyway we could get in earlier the service person told me "I should be grateful because some people have had to wait multiple days to get to their destinations." When we finally did board the flight the next day we were not served any food, no snacks, and no drink for the entire overnight flight."
Cons: "There was a 90min delay on all flights going to toronto due to construction in toronto yet air canada (knowing this) boarded everyone on time anyway and made us sit on the runway for over an hour. They could have left us in the lounge until they were ready. Parents with babies do not appreciate such thoughtlessness. But hey, as far as air canada was concerned, they left the gate on time."
Cons: "Seats are to close. There is no leg room."
Pros: "In the airport Chicago to Montreal I met a nice person he made my boarding pass to me. I love the service !!!!!! Said Thank you so much for your time to getting. Dory Clothilde"
Pros: "Seats, entertainment"
Cons: "We had to change planes, after boarding the original aircraft, and were delayed almost an hour. We thought the airline (Air Canada) could have recognized the inconvenience with a free drink or extra snack."
Pros: "I liked that we got a lot of food, and the movies were very good. Groups for boarding made sense and we boarded quickly"
Cons: "it was late and despite being 4.5 hours there were no free snacks or food. Only one toilet which we could never use bc of constant turbulence."
Cons: "Airline list baggage. Had to wait 3 hours to get luggage which was put it the next flight"
Pros: "Poor airline, always delayed, dreadful and unfriendly customer service. The only reason I flew with them this short trip was due to price"
Cons: "We were in Toronto for an entire week without our bag and Air Canada showed no concern at all for our well being. I travelled with my one year old son, I needed supplies for him and Air Canada gave me dead end numbers to call, websites that didn't work and even hung up on us when we were trying to find out about our bags. They treated us terribly. I will never fly them again."
Pros: "When there were unforseen delays. They just said too bad, here is a phone number you can call. It then took 2 hours to try and get someone on the phone. Once I finally was talking with someone, they said it would cost $200 to rectify the problem. I then got put on hold. When they came back they said it would be over $2000 to get home. Talk about trying to cash is on people's hard situations. I ended up flying WestJet. They were amazing."
Cons: "My flight was changed and I wasn't informed - I cleerly checked my information beforehand but it would be nice if flights were to change by two hours, to know in advance so arrangements could be made"
Cons: "It was so great we didn't go. Got a refund you retards"
Pros: "Nothing"
Cons: "Flight was late from Barcelona to Mintreal by an hour. I needed a wheelchair - didn't show up! Then pulled a muscle trying to get through customs and they barely held my flight to Chicago. Made it, with No Help. Late into Chicago and still no wheelchair. There was no one from whom to get help. Finally a United Airlines employee took pity on me and got a wheelchair to me and got me to the flight - again, just barely. Over 20 hours in the air, no assistance and poor food. I will never fly air canada again - ever. Not worth the savings. I've spent an entire week recovering and spent the savings on physical therapy due to the damage to my legs."
Cons: "horrible"
Pros: "The crew was attentive."
Cons: "The head phone slot did not work. Then the TVs went out which did not matter because I could not listen to them anyway."
Pros: "In flight entertainment. Friendly staff."
Cons: "Slight delay but related to the weather and not to the airline."
Pros: "luggage intact and well kept"
Cons: "No good refreshment on flight"
Pros: "There was nothing redeeming about this flight."
Cons: "Delay caused us to almost miss our flight to Dublin. Rude staff, and overall disappointing. I will not be flying on Air Canada again."
Cons: "Delayed"
Pros: "Plane was super old...peeling paint, barely any full size luggage space, no in flight tv and always late or delayed. 4/4 flights we took were delayed. This airline is the worst and were terrible at keeping us updated on delays or cancellations."
Pros: "Staff was friendly"
Cons: "Uncomfortable seating"
Pros: "Nothing to like about this airline. Horrible people especially in toronto, really unhelpful, extremely rude."
Cons: "Air line decided they didn't want me to take my connecting flight. Removed my luggage without consulting with me. Offered me a disgusting hotel. Forced me to pay out of pocket for food, taxis, transfers and my own hotel choice. Staff were so rude. No explanation to why they removed my bags. I made it in plenty of time for my connecting flight but airline had just decided. No staff member was interested in answering my questions or helping. They all just wanted to sod off home. they just didn't care."
Pros: "The plane was new and pretty clean"
Cons: "Food was horrible. Crew was useless. No organization."
Cons: "The departure time for the flight was 6:00am and there was no one in the check in counter until 4:15am. There was a long queue for the check in. Not a pleasant waiting time for the check in"
Pros: "Must bring your own electronic device"
Cons: "The temperature in the cabin was Frigid, even with blanket, 2 pairs of socks my coat & scarf I was freezing!"
Pros: "Quick flight"
Cons: "Delays"
Pros: "The food was very good, and the alcohol was free even the second time around which i liked"
Pros: "Very friendly staff."
Cons: "Left late so missed connection. Was put up in a mediocre hotel."
Cons: "Not enough time to go through customs. Missed connection."
Cons: "Deplaning and entering the terminal was delayed substantially."
Pros: "The crew was very nice."
Cons: "It was like flying in 1995. They may want to consider buying more modern planes."
Cons: "No free alcohol. Lights didn't turn off ever so I could get some sleep."
Pros: "The crew on the flight was nice, and the entertainment was good."
Cons: "Our first Air Canada flight was 2hr delayed due to mechanical error. After a 2hr delay, we finally flew for 1hr, had awful turbulence on the way down, and got to Toronto only to find out there was no customer service desk. We missed our connection with Luftanza and had to fly Air Canada again. First off, we couldn't get on another flight until the next morning. Then the desk never called the hotel they gave us the voucher for, so when we showed up at midnight the hotel was fully booked and had no room for us. We had to fly into Heathrow instead of Gatwick (final destination was Brighton for an international conference). We missed the entire first day of the meeting and had to rent a car for 65 pounds each to take us to Brighton from Heathrow, finally arriving at our hotel by midnight. The customer service was non-existent for Air Canada. We literally are going to have to email them."
Pros: "The flight was comfortable. Entertainment choices were varied and generous."
Cons: "o'Hare needs an upgrade."
Pros: "The crew was good!"
Cons: "I wished that there were opportunities given for beverages. I also would have liked more explanations on how to connect to the entertainment."
COVID-19 information

Safety measures for airlines flying from Chicago to Regina

Airlines flying from Chicago to Regina have enacted additional safety measures and adjusted policies to better accommodate travellers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago to Regina

Mandatory masks

Masks required on board, masks provided on flights from Chicago to Regina

Social distancing seating

Middle seats unavailable to book on flights from Chicago to Regina

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago to Regina

Flexible cancellations

Waiving of change fees. Search flexible flights from Chicago to Regina

Book cheap flights from Chicago to Regina

Recent round-trip flight deals

22/7Fri
1 stopAir Canada
7h 07mORD-YQR
26/7Tue
2 stopsAir Canada
10h 21mYQR-ORD
C$ 570
22/7Fri
2 stopsAir Canada
9h 27mORD-YQR
26/7Tue
2 stopsAir Canada
10h 21mYQR-ORD
C$ 575
22/7Fri
1 stopAir Canada
7h 17mORD-YQR
26/7Tue
1 stopAir Canada
8h 00mYQR-ORD
C$ 586
22/7Fri
1 stopAir Canada
8h 07mORD-YQR
26/7Tue
2 stopsAir Canada
10h 21mYQR-ORD
C$ 613
22/7Fri
2 stopsAir Canada
12h 47mORD-YQR
26/7Tue
2 stopsAir Canada
8h 21mYQR-ORD
C$ 619
9/3Wed
1 stopAir Canada
6h 39mORD-YQR
16/3Wed
2 stopsAir Canada
17h 56mYQR-ORD
C$ 620
12/3Sat
1 stopAir Canada
6h 39mORD-YQR
18/3Fri
1 stopAir Canada
7h 48mYQR-ORD
C$ 630
6/3Sun
1 stopAir Canada
6h 39mORD-YQR
19/3Sat
2 stopsAir Canada
8h 49mYQR-ORD
C$ 635
10/3Thu
1 stopAir Canada
9h 59mORD-YQR
13/3Sun
1 stopAir Canada
7h 48mYQR-ORD
C$ 657
11/3Fri
2 stopsAir Canada
19h 24mORD-YQR
19/3Sat
1 stopAir Canada
7h 48mYQR-ORD
C$ 663
12/2Sat
1 stopAir Canada
6h 19mORD-YQR
19/2Sat
1 stopAir Canada
8h 43mYQR-ORD
C$ 668
11/2Fri
2 stopsMultiple Airlines
16h 29mORD-YQR
18/2Fri
2 stopsMultiple Airlines
17h 56mYQR-ORD
C$ 684
10/3Thu
1 stopAir Canada
9h 59mORD-YQR
16/3Wed
2 stopsAir Canada
17h 56mYQR-ORD
C$ 691
12/2Sat
2 stopsAir Canada
19h 19mORD-YQR
16/2Wed
2 stopsAir Canada
17h 56mYQR-ORD
C$ 696
8/2Tue
1 stopAir Canada
6h 19mORD-YQR
16/2Wed
1 stopAir Canada
8h 43mYQR-ORD
C$ 709
11/2Fri
2 stopsMultiple Airlines
20h 31mORD-YQR
18/2Fri
1 stopMultiple Airlines
15h 43mYQR-ORD
C$ 716
12/2Sat
1 stopAir Canada
6h 19mORD-YQR
20/2Sun
2 stopsAir Canada
21h 13mYQR-ORD
C$ 731
11/2Fri
3 stopsMultiple Airlines
25h 55mORD-YQR
18/2Fri
3 stopsMultiple Airlines
31h 20mYQR-ORD
C$ 831
23/7Sat
2 stopsDelta
12h 34mORD-YQR
27/7Wed
2 stopsDelta
9h 47mYQR-ORD
C$ 1,060
21/7Thu
2 stopsDelta
12h 34mORD-YQR
25/7Mon
2 stopsDelta
11h 33mYQR-ORD
C$ 1,166

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17/2Thu
1 stopAir Canada
6h 19mORD-YQR
C$ 294
17/2Thu
2 stopsDelta
10h 15mORD-YQR
C$ 298
17/2Thu
3 stopsMultiple Airlines
16h 37mORD-YQR
C$ 474

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Chicago - Regina Flights

Departure:

Chicago (ORD)United States

Destination:

Regina (YQR)Canada

Return flight deals:

Regina - Chicago

Cabin classes:

Browse origins:

C$ 684

Browse destinations:

C$ 684