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1 adult
Economy
0 bags
Thu 3/9
Thu 3/16

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Good to know

Low season

March

High season

April

Cheapest flight

$474

Average price round-trip

$639

Good deal one-way

$297
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from St John's to Chicago Midway
(price for this month)
or less

FAQs for booking flights from Newfoundland and Labrador to Chicago

Top airline flying from Newfoundland and Labrador to Chicago

Scores according to KAYAK customer reviews
7.7
Porter AirlinesOverall score based on 2702 reviews
7.8Boarding
7.8Comfort
8.3Crew
6.8Entertainment
7.8Food
Airline reviews
Pros: "Nothing"
Cons: "Porter declined re-booking the flight due to weather conditions and forced us to purchase new tickets. Reservations made through anything other than Porter are treated poorly, service can be declined due to overbooking."
Read more about Porter Airlines
Pros: "Nothing"
Cons: "Porter declined re-booking the flight due to weather conditions and forced us to purchase new tickets. Reservations made through anything other than Porter are treated poorly, service can be declined due to overbooking."
Pros: "Efficient check in. Liked the shuttle bus service from subway to airport."
Cons: "As expected this is a commuter flight so very stripped down in terms of amenities. Tight plane seating and those overhead bins just barely accommodate the carry on."
Pros: "The crew was very professional."
Cons: "For a quick hop from Boston to toronto this was ideal."
Pros: "The crew was helpful and everything was on time."
Cons: "The ride was a bit rough at the end if the flight."
Pros: "Friendly crew"
Cons: "All good"
Pros: "It was absurd to pay $42 to check a small carry on backpack. The crew was rude, the air conditioning was unbearably cold, the flight was delayed several times and as a result I missed the event in New York that was the whole reason I booked this flight. My flight back to Toronto was also delayed."
Cons: "Free carry on bag, gracious crew, no delays, comfortable temperature. I will not be flying with Porter again after the experience I had."
Pros: "The crew is lovely"
Cons: "Porters flights out of Toronto have been significantly delayed every time I’ve flown"
Cons: "Flight was delayed"
Pros: "n/A"
Cons: "Was not offered a flight back to Ottawa, had to find a ride from Toronto to Ottawa once we landed .6 hours driving. See above."
Pros: "All ok"
Cons: "Not a thing"
Pros: "Fast and convenient"
Pros: "First time in 10 flights in 3 months flying with Porter in time - what a miracle!"
Pros: "Free bar nuts while delayed 10 hours"
Cons: "Kicked us out of the airport when connection cancelled, NEVER fly Porter!!!! The horror stories are true as could be"
Pros: "Nice quick flight - very comfortable."
Pros: "Clearing security was a breeze, the lounge is convenient, boarding easy and the plane was orders of magnitude more comfortable than what Air Transat offers."
Cons: "We sat on the runway for a while waiting to take off."
Pros: "Once we got on the flight it was fine."
Cons: "Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages."
Pros: "It was hassle free. Trace and arrival times were perfect. Thank you for caring."
Cons: "Got to Billy Bishop, only to find out flight is delayed 2 hours."
Pros: "Convenient, easy boarding, snacks and free wine on leg from toronto to chicago"
Cons: "Major delays that were poorly handled."
Cons: "Delay"
Pros: "fast"
Cons: "no TSA precheck"
Pros: "I liked the lounge"
Cons: "There were a lot of people and not enough outlets"
Cons: "Good"
Pros: "The flight was early!"
Cons: "It was uncomfortable because the flight was so long, and I couldn't stretch out very much"
Pros: "Nothing"
Cons: "Everything"
Pros: "Onboard crew was very nice"
Cons: "Crew didn't answer any of my questions, were snappy, and rude."
Pros: "Polite crew"
Cons: "Would like a sandwich instead of nuts"
Pros: "Efficient"
Cons: "Late flight"
Cons: "3 different delays. Sat on runway for over 3 hours in Toronto and then Newark. The one bathroom on the plane was full and started to overflow so we were sitting on runway for an hour and a half with no bathroom and could not get off."
Pros: "Liked the fact that I flew out of Toronto Islands airport, was fast and easy with complimentary snacks while waiting at the gate. I had an early morning flight and so beat the traffic, as I'm sure that picks up later in the day. Online checkin was easy and simple. I did not have any check-in luggage, only carry-on, suspect that also made it easier. The Porter airlines support call center was very helpful and friendly There were complimentary coffee and snacks at the gate... was a really nice feeling. Liked the waiting area at the gates, comfortable seating. Plane was on time. No issues"
Cons: "I had an early morning flight, so traffic was very light, but suspect that later in the day. So taking a later flight on Porter may be problematic as getting to the airport would be more difficult. The language in the email ticket confirmation made me a little concerned, as it mentioned having to re-confirm the booking and being at the airport at least 3 hours ahead even though the flight time was only 1:05 hours etc. But after calling in to the support center, the concerns were cleared up."
Pros: "Although our flight was delayed about 40 mins., the lounge was comfortable and with privacy between seating areas. There was also complimentary coffee, tea, water and cookies. Boarding was quick and easy and the flight was comfortable."
Cons: "If Porter was a budget airline the dreadful customer service might be partially understood, but it's not. Somebody needs to put passenger considerations into operational planning for situations where travel plans are disrupted, especially when they are because of mechanical or airline problems."
Pros: "Quick and convenient boarding, terrific airport, generous terminal lounge for relaxing pre-flight."
Cons: "Louder than a usual commercial flight, probably due to being a turboprop aircraft."
Pros: "There were mechanical delays, so Porter gave an $8 voucher to spend in the airport, which was a nice touch since I had never received that from other airlines who also had mechanical delays."
Pros: "It was on time"
Cons: "We had to make a second pass at Halifax due to a glitch"
Pros: "Porter Airlines is the best I've been on within North America. Delighted that my 2nd flight was still Porter."
Pros: "Breakfast, bars, etcnithin"
Cons: "Nada"
Pros: "Lounge with free drinks (soda, coffee, water) and cookies/snacks! Glass drinks glasses on the plane! And leg room!"
Cons: "I fly weekly for work, but last week I got to fly to Toronto for pleasure to see my fiancé. In all of my years of traveling, I have missed a flight maybe 5 times due to traffic, weather, or other uncontrollable factors. It happened to be that on my way to Chicago Midway, there was an accident on the road that stopped traffic dead for 40 minutes. When I arrived at the airport, I begged for people to help me out by letting me cut security lines so that I wouldn't be late, but alas...others were also rushed and the TSA agents weren't too helpful. I arrived at the gate for my flight about 3 minutes late in defeat. Oh well - it happens! What was really unpleasant was that nobody would help me out. I was charged $150 to "change" my flight instead of just getting rebooked on the next one the way any other airline would happily do. And to top it all off, I was given the runaround with 3 different Porter employees diffusing responsibility. I will be moving to Toronto after the wedding but will still work out of Chicago - which means that I could provide business to Porter Airlines for the next few decades! Because of this poor service, you have lost my business. I would rather fly with another airline where customer service is a priority. Losing years of a customer's weekly business over a $150 fee seems to me to be a rather poor business model and I am sorry that the bureaucratic rules in this case could not be bent."
Cons: "The crew were mostly great except one female flight attendant who was unnecessarily rude on two occasions on the short flight."
Cons: "The fee for my bag was too high!"
Pros: "Not sure if this is Porter Airlines or the airport, but the lounge at Billy Bishop Airport is fantastic. Free water, coffee, and snacks - it is so home-y in there, which is amazing when you are away from home :)"
Cons: "N/A"
Pros: "Departing from Billy Bishop is amazing. Incredibly quick and convenient. Complimentary nacks and drinks in the gate area?!"
Pros: "Porter lounge in Toronto"
Cons: "Nothing!"
Pros: "Nothing"
Cons: "As I was waiting at my gate for my flight, I notice that It's almost time to board the plane & there is no plane at my gate. I walk over the the lady's at the stand and ask if I'm at the right gate and this is when I'm told that my flight had been CANCELLED and no one thought to inform me. One of the ladies goes "You should have received an email" but I know that I'm not the only who was unaware of the flight cancellation as I found out later that 3 other people had been going through the same thing. On top of the terrible communication, once I finally got booked on the next flight out, I was sat beside the most obnoxiously loud & irritating person I have ever met. He was swearing and raising his voice the whole flight and the flight attendants completely ignored it. There was a small girl in front of me with her father and he tried to confront this man and tell him to lower his voice & still, the crew payed no mind. Also, I am an 18 year old girl flying by myself for the first time... This man kept poking me in the arm and leg trying to get my attention and was trying to get all this personal information out of me. This is harassment and if I had flown with a bigger airline, this dude would have been off the plane before it even took off. I was petrified the whole flight as he kept telling people that if the plane didn't take off in 30 seconds, it was going to CRASH. I had one of the worst anxiety attacks of my life & the whole situation was ignored by the crew. I WILL NEVER FLY WITH PORTER AGAIN."
Pros: "The service"
Cons: "The flight deleyed"
Pros: "Service. Location of both Toronto Island and Chicago Midway are closer to downtown than the bigger airports in each city."
Cons: "Porter was a nice, small, well-kept secret. Now they have expanded quite a bit and the lounge is always full, to the extent that people are sitting all over the ground. Flights are almost always late to take-off. I guess all good things must come to an end."
Pros: "Excellent. Polite service, free (and tasty) food + beverages, (dry and otherwise) comfortable seats, other customers polite, bilingual announcements, fast + efficient. Really impressed! Good price too."
Cons: "Nothing, really! No in-flight entertainment besides a magazine, but all short flights anyway."
Pros: "I took Porter many times in the past. Many delays, never major, and I found landing at city airport were convenient enough to Override the annoyance of the delays."
Cons: "This time my flight was cancelled. For no particular reasons (not due to weather). That was the only flight that was cancelled of the whole day. All other were flying. They did not say why. My guess is not enough passenger on the flight to make it worth it to fly for them. They rebooked me 24 hours later. I called customer service to ask for support and I received no support at all. I explained I was having a high risk pregnancy and was out of medication and needed to be at my DR appointment I had the next morning in Chicago. They said that there's nothing they can do. They also said additionally we also want to mention that we do not support for accomadation cost. I did not even ask but it's like they wanted to highlight that no support is given. I asked to speak to a supervisor. Told him I would like support to rebook a non Porter flight to get on time to Chicago. Again he said I am sorry we don't do that. I mentioned I was shocked that they don't even care that I was saying it was a medical reason and I asked for his name saying I will hold Porter responsible if any difficulty would happen because of this. At that point they searched for a solution. He said ok you can be on a flight but you need to board in 30 minutes. Impossible for me to do where I was but this should have been proposed to me earlier so I could have made it. And I would have done it. Second solution he gave me was to be in Ottawa boarding in 1 hour. Again impossible I was in Montreal with no car. He said you cannot hold me responsible if anything happen with your pregnancy I offered you solutions. Thank you Porter all impossible to do at the time you offered them. If you offered them all to me on time that would have maybe be possible. Anyway they made me miss 2 days of work + my doctor appointment I had to go without medication for a few days + paid for a extra hotel room. Next time I am taking air canada delta or United . I will pay more but at least I will have the guarantee to be taken in charge by their customer service if delays or cancellations happen."

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Recent round-trip flight deals

6/14Wed
2 stopsPorter Airlines
11h 17mYYT-MDW
6/23Fri
2 stopsPorter Airlines
9h 20mMDW-YYT
$474
6/14Wed
1 stopPorter Airlines
10h 47mYYT-MDW
6/23Fri
1 stopPorter Airlines
8h 50mMDW-YYT
$697
6/14Wed
1 stopPorter Airlines
10h 47mYYT-MDW
6/23Fri
1 stopPorter Airlines
8h 50mMDW-YYT
$698

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