Find cheap flights from Chicago to Regina

CHI - YQR

Find cheap flights from Chicago to Regina

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Chicago (CHI)
Regina
Thu 12/2
Thu 12/9
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Good to know

Low season

March

High season

February

Average price round-trip

$624

Good deal round-trip

$426
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 20% increase in price.
(avg. price over the last 2 weeks)
or less

When to book flights from Chicago to Regina

Estimated round-trip price
Average price per month

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $426 or less round-trip.
  • High season is considered to be January, February and March. The cheapest month to fly is March.

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Top airlines flying Chicago to Regina

Scores according to KAYAK customer reviews

7.7
WestJet
Overall score based on 9,062 reviews
8.1
Boarding
7.7
Comfort
8.5
Crew
7.0
Entertainment
7.1
Food
Airline reviews

"seamless experience, thank you."

Pros: "Nothing same useable"
Cons: "No need"

Pros: "Crew was amazing"
Cons: "sing us to be about an hour late @2:15am"

Cons: "Cramped seats entertainment"

Pros: "Arrived early."
Cons: "Uncomfortable seating for a tall person. Cut out the drink and snack service. People can toughen up. Just offer water without using the snack cart."

Pros: "Crew."
Cons: "Entertainment aka movies.. this was an older plane - should have brought a book as I’m used too movie screens"

Cons: "Bathroom had no light Seats hard and uncomfortable Did not offer any entertainment rental like Air Canada"

Pros: "Crew."
Cons: "Timing. The flight was delayed by an hour."

Cons: "Sat in Plus. Horrible service. No hot towels. Had to ask for 2nd drink and was refused a coffee and Baileys with at least an hour left in flight. No snacks offered or served. The attendant spent most of her flight hiding in her seat and reading a novel. Brutal!"

Pros: "The flight crew was excellent. Pilot definitely had his passengers in mind. Landing in windy Regina was perfect"
Cons: "The cabin person upon entering sucked a lemon apparently"

Pros: "Our l;uggage did not make it to palmSprins, our final destination It seems they found it, but has not delivered to as as of 11:00am, 1/5//2019. We arrived Palm Springs 1/4/2019. 12:20am. Still waiting!"

Pros: "The crew was great overal. Great sport and attitude with humor."
Cons: "The flight in Ottawa was delayed twice which made me change my plans twice. The plane was also a little cold heading to Toronto. Otherwise the help from Paul getting checked in was fantastic. He made the bad situation of a delay worth it just talking with him and apologizing for the delay with true empathy . Thank you Paul"

Pros: "Very friendly and helpful staff at both baggage check-in and during flight. That is why I fly WJ."
Cons: "Leg room on plane."

Cons: "Plane was delayed. Wanted to sleep during flight but couldn’t because flight attendants were chatting loudly amongst themselves"

Cons: "Morning flight but flight was late leaving even though the plane was at the terminal. Sat on the tarmac for a half hour waiting in line to takeoff."

Cons: "Super Cold airplane and it’s not the only west Ket that was freezing. the crew kept skipping my row for drinks for some reason. the landing was rough."

Pros: "The stewardess was awesome."

Pros: "Airport services were excellent. Wait at check in and security were very little, just a few minutes. We had an awesome experience on both Calgary and Montreal sides"

Cons: "Crew not so friendly"

Pros: "Upbeat crew!"
Cons: "Leaving from the basement of YYC airport"

Pros: "Great staff and helpful with checking bags."

Cons: "Being late"

Pros: "Flight delayed but gate agent sped up boarding to make up lost time"
Cons: "Q400 not a comfortable aircraft. Lack of baggage space."

Pros: "Everybody was nice. It was my second time flying and they sure do make you feel comfortable."
Cons: "Nothing I didn't like. It was great all around!"

Pros: "Staff are very welcoming and helpful."
Cons: "Two worst landings I have experienced. Boarding is always chaotic on Westjet"

Pros: "The flight was on time both boarding and landing. My checked baggage was there when we arrived at the baggage spot. This was the best part."

Cons: "No movies available"

Pros: "I liked the timeliness of boarding."
Cons: "Crew was not the nicest, especially when asking for non purchase items like water."

Pros: "GREAT CREW"
Cons: "BOARDING FROM OUTSIDE-VERY COLD OUT IF I KNEW I WAS BOOKED ON A PROP PLANE I WOULD HAVE BOOKED DIRECT SEAT SIZE-CRAMPPED-I ASK THE GUY BESIDE ME IF HE WANTED THE AILSE BECAUSE HE WAS TALL AND SQUISHED CALL ME ANYTIME 306-551-3251 THAT WAY I WILL KNOW THE VALUE OF THIS SURVEY"

Pros: "The professionalism. The crew were wonderful. Thank you for the great service."
Cons: "The only problem we had with Westjet was the ramps from the plane to the terminal in Calgary. Pretty steep and my husband tripped on the metal platform on the carpet. He banged his head and hurt his leg. Westjet crew were fabulous! They tended to him right away. The paramedics were called and he's in hospital right now."

Pros: "Re-booked on Westjet after my WOW airlines was cancelled. Didn't know what to expect - pleasantly surprised, Great service from top to bottom leaving Gatwick Airport. Will make them my top preference in searching future flights out that way."
Cons: "Nothing - the entire experience (check-in, flight, deplaning) exceeded my expectations."

Pros: "Wonderful service!"

Cons: "I was given a ticket with the seat 3A (one of the plus seats); I didn't ask for it or pay for it, I just got that seat when I was checking. After I found out it was a plus seat, I acknowledged to nearby the flight attendants and nearby passengers I didn't pay for this, that there was a mistake, and I could move if there was someone who did pay for it. What I received from the flight attendants are accusatory remarks/comments about how shouldn't be there because I didn't pay for it (after I acknowledged this before anyone even had an issue about it) and passive excuses that didn't make much sense when I asked them why there ws this issue in the first place. I was fine with moving seats from what I was initially assigned to, I was fine with being moved twice thereafter (first moving to 21E, then to 23E). What I was not fine with was 1. the accusatory tone by the flight attendants that I tried to take someone else's seat 2. even though I was given the seat by the person at the check-in desk when I didn't even ask for it and 3. after I was the one who initially brought up this issue in the first place and was willing to changet seats with he rightful passenger. Please learn to take responibility for your actions and mistakes and errors rather than blaming it on a passenger who just wants a safe flight home. Thanks."

Pros: "Direct flights...friendly staff...well kept aircraft..."
Cons: "Long wait to board due to people checking in on line and having to show passports at the last moment...delaying boarding for everyone else..."

Pros: "I liked the ease in getting through security."
Cons: "Indidn’t Like that that the flight was delayed by more than 1 hour. I really do mean t believe that it was because the pilot was late. I think that it was a way to arrive at the Regina airport when other planes arrived to save airport fees."

Pros: "Overall flight and connections were good. Board process was smooth and flight departed and arrived on time. Watch for baggage delays when arriving in Fort McMurray as they can sometimes be excessive. No entertainment provided on the smaller planes but most people have some form of entertainment with them."

Cons: "Screen was broken Not much room for kegs"

Pros: "the westjet app is great. however the flight home did not have it.."
Cons: "on our westjet to Puerto Vallarta the air conditioning vent above my brother's seat dripped all over him. on the trip back the screen on the back of the seat in front of my other brother didn't work so we had to share. not terrible, but a little annoying considering the amount we pay for tickets."

Pros: "The airline attendants were very friendly"

Pros: "Friendliest crew, good entertainment system. Comfortable seating"
Cons: "Desperately need a lounge facility in terminal 5 Chicago"

Cons: "The media system barely worked."

Pros: "I felt comfortable"
Cons: "Hearing announcements weren't clear"

Pros: "Staff"

Pros: "Screaming movies"
Cons: "Arriving over a hour late then staying on the tarmac in Orlando for another 45 minutes as the gate wasn't working when there was plenty of other gates available."

Pros: "Always a good experience travelling with west jet"

Cons: "Good airlines"

Cons: "Took 30 minutes from push-back to runway in TO. Cabin was unpleasantly hot."

Pros: "Really fast"

Pros: "Fast and efficient service, new plane with nicer seating."
Cons: "That you have to pay for coffee and drinks that are normally complimentary."

Cons: "Good flight"

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."

Pros: "Attendant Wendy was fantastic in service and friendliness."
Cons: "Once again big guy put into seat 33F. Seat doesnt go back and no legroom."

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."

Read more about WestJet
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 travelers. 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

Book cheap flights from Chicago to Regina

Recent round-trip flight deals

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