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Find cheap flights from Newfoundland and Labrador to Chicago

Find cheap flights from Newfoundland and Labrador to Chicago

Round-trip
Economy
Boston (BOS)
Chicago All airports
Wed. 20/1
Wed. 27/1
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Good to know

Low season

August Best time to beat the crowds (3% less expensive on average)

High season

December Most popular time to fly (8% more expensive on average)

Average price round-trip

C$ 435 (avg. price over the last 2 weeks)

Good deal round-trip

C$ 203 or less

Good deal one-way

C$ 145 or less

FAQs for booking flights from Newfoundland and Labrador to Chicago

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Top airline flying from Newfoundland and Labrador to Chicago

Scores according to KAYAK customer reviews

7.1
Air Canada
Overall score based on 24,775 reviews
7.3
Boarding
7.0
Comfort
7.7
Crew
6.9
Entertainment
6.5
Food
Airline reviews

Pros: "Seats were nice to recline and the in flight tv is much nicer than tablets etc. The in flight safety video is good and quick easy"
Cons: "Seriously? No free snacks? It's ridiculous that you want us to purchase snacks. Something small should be complimentary. Staff was in ok moods but a little edgy. The air was too cold."

Cons: "At the gate, we were told our plane would leave soon. An hour later, they announced the flight was cancelled and we were briskly escorted out of the terminal, told to go through customs and pick up our luggage, which had never even made it on to the plane. They were not re-booking flights at the airport, and the phone lines went to a voice mail message telling us to call back in a few days. I was stranded in Toronto with no phone and no where to stay. It's a week later and I still have not heard anything from from, even though I've called and emailed and sent snail mail."

Pros: "The flight arrived about 30 minutes early. Also, it left a little late. For me, the less time on the plane the better."
Cons: "Guy next to wanted to charge phone a laptop in USB port in front of me b/c his was our of order. This worked out OK but in a small space it's not so good. He was bare foot too. Take of your shoes but wear socks, please....Plane was not hot, actual a litter chilly."

Pros: "I enjoyed the crew, the food and the entertainment. The crew did give us peanuts for our extra 5 hours on the plane."
Cons: "We were 3 hours late for departure and took 2 extra hours in the air because of re-routing. The seats were abnormally stiff and went back so little that it was extremely hard to fall asleep during the 18 hours we were on board. The crew was unwillng to let us bring our instruments on board and thus, they cracked from the air pressure during the flight."

Pros: "Service flight on time food"
Cons: "No movies for 7 hour flight"

Pros: "Low fare"
Cons: "Flight delayed initially due to weather. When weather cleared flight delayed half hour because they could not find the pilot."

Pros: "Departure was orderly and staff interactions good"

Pros: "Boarding was good, but pretty bad flights overall. One of the worst I ever had in my life! The plane seats we had had so little cushion that is was painful to sit. My husband was avoiding touching the back by leaning on his arms and he is great shape, don't think elderly and in pain by himself...Entertainment simply non-existent and food as well... The crew were borderline okay. Plus the plane drove for about 20 minutes at Montreal and about 20 in Chicago before we left and after we landed...Let's say I saw parts of O'Hare in Chicago, I didn't even know existed!!!"
Cons: "Pretty bad flights overall. One of the worst I ever had in my life! The plane seats we had had so little cushion that is was painful to sit. My husband was avoiding touching the back by leaning on his arms and he is great shape, don't think elderly and in pain by himself...Entertainment simply non-existent and food as well... The crew were borderline okay. Plus the plane drove for about 20 minutes at Montreal and about 20 in Chicago before we left and after we landed...Let's say I saw parts of O'Hare in Chicago, I didn't even know existed!!!"

Cons: "no entertainment and poor seat selection"

Pros: "Love the individual entertainment & the friendly staff team"

Pros: "The flight attendant was very nice and smiling."

Pros: "$800 reimbursement 1st class"
Cons: "They overbooked the flight by 2 passengers."

Pros: "service on the plane was good and the crew was very nice to be patient while we boarded the plane with 3 little kids"

Cons: "I arrived at the gate and looked at my ticket to see "GTE" where the seat number usually is. I was informed upon arriving at the desk at the gate that that meant Air Canada has also decided to participate in the ridiculous practice of overbooking their flights and that even though I purchased my ticket roughly 8 weeks prior, there was a chance I might miss my flight to my friend's WEDDING. The lady who was working the desk was as unhelpful and dismissive as you could possibly imagine, refusing to look at me and giving me attitude for merely waiting in the area to see if anyone had missed the flight so I could get on. It was surreal; the only way I could describe her incomprehensible behavior would be to say it was as if her boss were right in front of her and she was trying her damnedest to get fired. It was one of those situations where you could tell this miserable, miserable person was enjoying the power trip she was on and doing everything in her power to make me feel helpless and angry. I made my flight, miraculously, but it was the worst customer service experience I have ever had in my life, airport or not."

Pros: "Nothing"
Cons: "Everything. Plane was ready to leave on time but had a delay of almost an hour due to construction in Toronto. Connecting flight was held in Toronto and despite getting to gate almost an hour before departure, they changed passengers to another flight causing total delay of four hours. Air Canada staff were indifferent and uncaring. Unfortunately with no real choice in airlines to Newfoundland we are stuck with Air Canada."

Pros: "Professional fight attendants, very nice."
Cons: "The flight took off late but most of the lost time was made up during the flight time."

Cons: "Flight was late so I missed my connection. Then my luggage was delayed by five hours behind me. Generally poor service."

Cons: "Kid crying and yelling the whole flight"

Cons: "Flight delayed, service with discrimination, pride, specially male crew, this is a really bad flight experience."

Cons: "very comfortable flight with free movies."

Cons: "It was so late, I almost missed my connecting flight. They were not helpful. They did not communicate well and they refused to take any responsibility."

Cons: "Very bad cabin pressure -- lots of ear pain."

Pros: "Again, nice selection of entertainment and great crew."

Cons: "There was some dripping from the ceiling on those of us in the back of the plane. It might have been condensation from the air conditioning or air flow nozzles. In the groove of the ceiling immediately over the seats there seemed to be some dirt or mold."

Pros: "Not much can go wrong on a flight shorter than 90 minutes."
Cons: "3 delays that added up to 1 hr, but counter personnel kept us informed."

Pros: "I . was impressed with the food and service.over all the whole trip was very good"
Cons: "there was nothing I did not like"

Cons: "Moving through security and customs in the Toronto airport was incredibly slow, with 4 or 5 checkpoints, all with lines. Staff were polite but there were not enough of them. We almost missed our connecting flight, and our bags apparently did miss it, because they have not yet arrived in Chicago (see previous comments). Air Canada should have seen the problem in terms of timing with the connecting flight and expedited better. Will try to avoid Air Canada in the future, especially if there are connections in Toronto."

Pros: "All went smoothly"

Pros: "We left and arrived early, the seat was surprisingly comfortable (it helped that there were lots of empty seats, including next to me), my full-size carry-on fit easily in the overhead bin, despite it being a small plane, the in-flight entertainment was always on and pretty good... everything went well."
Cons: "Only the things I've grown to expect on any domestic service (e.g., no food)."

Cons: "if you get in a que, then the computer goes down , your dead, AC line will be 1.5 hours to get to rebook. then you have 2 day to stay before you can get out. if you decide to go on delta because staying 2 day in hotel is more expensive than buying a new ticket ac will not refund you. Air Canada is the least flexible airline in the world relative to refund."

Pros: "Tv in all seats, individual air controls, the crew was nice and I offered up my bag to go on the checked bags when asked and it was the first one out on the bagged claim"
Cons: "I'm 5'8 and my legs hardly fit when sitting straight in the seat"

Pros: "was forced to spend the night in Toronto because Air Canada didn't seem to know that there would be a huge crowd at the airport that evening. I was told as I exited my flight that I would not make the connecting flight and I had to spend the night in Toronto. I will never fly Air Canada again"

Pros: "The crew members in both the flights were amazing. they seemed like they enjoyed their job. Its not very common at Air Canada."
Cons: "The flight from Chicago to Toronto was delayed by half hour. But the boarding gate agents did not even mention the delay."

Cons: "after wetting half hour in the line they said i didn't pay for my ticket and tell me to parches a new ticket"

Pros: "Nothing"
Cons: "Air Canada service"

Pros: "It was comfy. Individual screen."
Cons: "We took off 25 minutes late and no food was served, not even a snack. I had to pay 25$ to check in my suitcase."

Cons: "Flight was late"

Pros: "Run by united but more efficient than a recent Air Canada flight."
Cons: "3 hour flight and had to pay extra for entertainment. Only two biscuits given for food. Cramped seats for anyone 6ft tall."

Cons: "I could not check in online for both legs of the flight. Stuck in the middle seat even though I was ready to check in 24 hrs prior."

Pros: "Overall it was good. The crew was very friendly. The plane was small and it was a short flight, so everything else was average as expected for a short flight."

Pros: "Flights on time"

Pros: "The crew was good and the in-flight entertainment options were decent."
Cons: "Plane took forever to take off because we were waiting for people late from layovers. Got one drink, no snacks, nothing else. Plane arrived over an hour late."

Cons: "It was a United flight and everywhere it said it was Air Canada instead of United. Hopping terminals and running through them last minute is not fun. To top it off the flight got delayed a ton of times and messed up our schedules completely."

Pros: "Everithing-----Ramesh"
Cons: "Ramesh"

Cons: "delayed 2-3 hours in Vancouver so missed connection, had to rent a vehicle to get home. Everytime, United into O'Hare… never again!"

Pros: "Cancellation came with a new flight and coucher for sleeping overnight at a O'Hare Hotel which was very well organized and went smoothly. Staff at ORD were waiting for us and very helpful."
Cons: "Was unable to check in my Air Canada flight the day before to find out the next day, at the airport that the flight was cancelled. The Air Canada flight was operated by United and no such information was provided in my reservation on Kayak or at the Air Canada counter in SAN airport, so I had to guess that another Star Alliance member would be taking over."

Pros: "The flight was on time"

Cons: "Gate was changed after check-in, but lack of announcements nearly caused my 84 year old mother to miss her flight, which was changed from gate 80 to 62."

Pros: "Was somewhat of a comfortable flight not much leg room at all and there was no earphone jack to be seen for my seat. The cost of food is ridiculous and if you wanted WiFi you had to pay for it. With the prices we pay for tickets and seat selection you would think that they'd offer at least a sandwich for free. Crew were great though very pleasant."

Read more about Air Canada
COVID-19 information

Safety measures for airlines flying from Newfoundland and Labrador to Chicago

Airlines flying from Newfoundland and Labrador to Chicago 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 Newfoundland and Labrador to Chicago

Mandatory masks

Masks required on board, masks provided on flights from Newfoundland and Labrador to Chicago

Social distancing seating

Middle seats unavailable to book on flights from Newfoundland and Labrador to Chicago

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Newfoundland and Labrador to Chicago

Book cheap flights from Newfoundland and Labrador to Chicago

Recent round-trip flight deals

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