Find cheap flights from Chicago Midway Airport to Maine

Find cheap flights from Chicago Midway Airport to Maine

Round-trip
Economy
Chicago (MDW)
Maine
Sun 11/29
Sun 12/6
Any month
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Top tips for finding cheap flights to Maine

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be October, November and December. The cheapest month to fly to Maine is August.
  • Morning departure is around 515% more expensive 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 - booking Maine flights

How long is the flight to Maine from Chicago Midway?

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Are there Maine travel restrictions currently due to Coronavirus?

How does KAYAK find such low prices on flights to Maine?

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What is the Hacker Fare option on flights to Maine?

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Top airlines flying Chicago Midway to Maine

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,796 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "Decent entertainment options and snack offerings."
Cons: "Last 6-8 rows were vacant and for some reason Someone was still seated directly next to me. Why on earth the flight attendants (otherwise great) didn’t make an announcement that there was no need to share a row and encourage people to spread out is beyond me. I mean this is the only flight I can remember in a decade that wasn’t nearly or fully booked, you’d think they’d emphasize that. Instead I got to be trapped like it was a full flight next to a guy with no concept of personal space."

Pros: "The crew was good"
Cons: "The plane was extremely hot."

Cons: "Flight was delayed and completely packed so our family could not get seats together"

Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."

Pros: "The entertainment"
Cons: "Space between"

Cons: "Stop being LATE!!!!"

Pros: "Food &entertainment"
Cons: "Mechanical problems flight delayed 2 1/2 hours"

Pros: "The crew was very polite and accommodating."
Cons: "Seats are uncomfortable and tight."

Cons: "Plane was way too hot and stuffy, wasn't until about 20 min into flight before started to cool down."

Cons: "At least one hour late"

Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."

Pros: "wonderfu crew... very helpul`"
Cons: ".."

Pros: "Flight was on time and arrived a little early."
Cons: "I was seated next to a very large man (6’5” he said) and had no room in my seat. Thankfully the seats in front of us were empty and the flight attendant moved him."

Pros: "great service, easy to get on and off, snack options and drinks were all great"

Pros: "Friendly crew"
Cons: "Business class seats were short whdn lay flat. Metal footrest at the end made it uncomfortable to hang feet off the end. Little privacy"

Cons: "Ran out of snacks by the time they got to my row"

Pros: "The flight left on time and landed 15 mins early. Staff was nice and attentive."
Cons: "The organization for boarding in zones."

Pros: "Uneventful and on time"

Cons: "We were on the tarmac for almost 2 hours. It's probably LaGuardia but the experience was very bad."

Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."

Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"

Pros: "Friendly and courteous attendants."
Cons: "Had a seat that did not recline...not broken just one of those seats."

Pros: "Short flight"
Cons: "In SLC they boarded by row numbers and not zones. Weird..."

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: "Good customer service"

Pros: "The flight is short"
Cons: "Delayed from 930pm to 6am. Didn't tell us till almost midnight. Because of scheduling issues not weather or anything. The check in people had no idea what I was talking about when I tried to check in for my 6am rescheduled flight."

Pros: "Quick friendly service from crew and captain."
Cons: "First class seat was broken was reclined and super uncomfortable the whole flight the plane was super outdated and old."

Cons: "Flight was delayed nearly 2 hours without any compensation to the passengers. I frequently fly jet blue and whenever they are that delayed not weather related the staff frequently gives the passengers a complimentary cocktail. Also your boarding process makes little sepnse to me why board from the front of the plane more sensible to board back to front"

Pros: "Seats are comfortable. These short haul flights often have worn out, painful seats."
Cons: "They do a bad job of screening people with bags too large for the overhead bins and then those people have to check one they have already tried to board and it slow things down."

Cons: "All was well"

Pros: "Delta auto-booked me so I didn't have that worry once I arrived in Atlanta."
Cons: "Their system gives too-short layovers so any delay at the point of origin means a risk of missing connections. Many people on my flight were worried about connections because Delta delayed our start by over 30 minutes to "change a switch," whatever that means. Then for passengers with short connection times, they should NEVER be seated in the rear of the plane when it takes 20-30 minutes for the rear-seated passengers. Not very consumer-oriented."

Pros: "Free meals! Free snacks! Free movies! Comfortable seats and friendly flight attendants!"

Pros: "Everything was excellent."
Cons: "Cant get used to cookies and drink service on long haul flight. Do not care for salable food choices so packed a sandwich."

Pros: "Service was excellent. The food was great. The in-flight entertainment was a impressive and a life saver. We will fly Delta again."
Cons: "Nothing negative to say."

Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."

Cons: "Everything that could have gone wrong with my flights, went wrong. On my way from LA to Raleigh (through Atlanta), I was affected by the weather conditions at Atlanta. I understand that the weather is beyond Delta's scope of control, but customer service is not. I had to wait in line at LAX for 8 hours to even get information on what had happened, and what solutions were available. The customer service call center was collapsed, and at the airport counters at one point there was ONLY ONE DELTA REPRESENTATIVE serving a line of more than 100 upset customers. This IS Delta's fault, and it is unacceptable. This definitely was under Delta's control, but in order to save a few dollars in overtime for emergency staff Delta was willing to let its customers make terribly long lines, miss their flights, their connections and consequently their commitments. It is disappointing to observe how Delta believes that a few dollars saved on extra staff and emergency measures can offset the irreparable long term damage to its business due to upset customers. My way back from Raleigh to Los Angeles was also a disaster. Without any type of explanation and nothing more than an email announcing the change, the nonstop flight I bought was replaced by a 1-stop flight with connection in Atlanta. This was NOT THE PRODUCT I PURCHASED. There is a reason I paid a premium for a nonstop flight, and Delta did not hesitate in providing me with a less valuable product without any explanation or refund. Delta prioritizes its operational metrics - an obsession to fill and overbook its capacity - over its customers' experience, one again under the foolish belief that short term savings in any way offset the long term damage of disappointed and alienated customers. I will NEVER FLY DELTA AGAIN. I will do whatever I can to transmit my experience to everyone I know. At a time where major airline carriers are in the spotlight due to abusive practices (i.e. the United passenger case), I still find hope in knowing that alternatives such as Southwest still put their customers first, over the ethereal benefits that a few-dollar savings in operational expenses can provide."

Cons: "Boarding was ok however person sitting next to me, her seat was double booked. Luckily the other person also got Comfort seat."

Cons: "Agents at the ticketing countet were the rudest i have ever encountered in my years of flying. Had a problem and when i asked for their assistance was given the Delta 800 number and told to call and they walked off. When i called it was a 2 hour wait for an agent. Thank goodness for their app as i was able to.change my flight with the My Delta app. Also they had overbooked the flight and rather than giving assurance to people just told us to wait and "line up orderly"."

Pros: "One of the male flight attendants was very nice"
Cons: "No food was provided, there was a throw up stain on my first flight to Atlanta then on my connecting flight there was crumbs on my table, my boyfriends table did not want to close so that caused discomfort to the person in front of us. Boarding time took a very very long time"

Pros: "Length of flight was good, one of the flight attendants was very nice"
Cons: "Flight attendant arguing and having words with a passenger BEFORE the flight even took off was very alarming, the attendant had walked past the seat, we saw her face change, she halted and walked back to the passenger and a very heated and negative exchange ensued, then another flight attendant came out and threatened to evict the passenger from the flight, this was before the flight even took place .... all passengers were like just remove them already ... t his is a short flight and most of use were connecting from a long flight from overseas ...."

Pros: "Flight attendants were competent."
Cons: "Air conditioning was extremely noisy."

Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."

Pros: "Good experience given that it was a long flight."
Cons: "How about meal service on the 5hr flight from Atlanta to Portland? The food for purchase options left much to be desired."

Pros: "Food and wine"
Cons: "Seats are difficult to sleep in"

Pros: "Smooth boarding, no delays, quiet easy flight, arrived on time and quick deplaning."

Pros: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."

Pros: "Just absolutely uneventful and quick."
Cons: "TSA"

Pros: "Overall flight was nice, but almost miss my flight!"
Cons: "Almost miss my flight due to Delta being short staffed at the ticket counter in the early am. Had a small issue to validate my passport in the automated cheek-in botths and waited over an hour to get them to personally validate. terrible experience. There were several of us with the same problem. I chose Delta given their prestige for great customer service, but they definitely need to do something about some of the folks at Logan's terminal."

Pros: "I liked nothing about my flight. It was like being waterboarded and held up for my money at the same time. How can you fit so many tiny seats on one plane. And then have 80 year old woman berate us if we as much as have to go to the bathroom. I understand that there is a profit margin,but treating people so poorly is a nice way to do it."
Cons: "The service, the tiny seats, the filthy plane, the gross food( why even bother?) the rude flight attendants and being told I was flying Air France when actually it was a horrible American carrier."

Pros: "They sat my family together and the crew was amazing."
Cons: "The seats are really uncomfortable and the flight was really packed with all this covid stuff."

Pros: "I liked the price and that it was a direct flight"
Cons: "Everyone was moved around a lot to try to social distance so I was closer to more people than I would have been on a regular flight."

Cons: "I had problems with baggage and Allegiant staff at the airport were very unhelpful."

Pros: "Quickness, efficiency"
Cons: "Nothing. I received all I expected."

Pros: "Crew and plane ride."
Cons: "The seats hurt us."

Cons: "I would have liked to have a drink of water for free!!"

Pros: "Fantastic! Smooth sailing!"

Pros: "Left on time, arrived early, deplaned quickly because no one had bag"
Cons: "Reclinable seats"

Pros: "Cheap and direct no frills"

Pros: "Direct flight was very nice. Took off on time and arrived slightly early. Flight crew was friendly and efficient."
Cons: "Baggage check not staffed until 2 hrs before flight and then it's a 20-30 minute wait to check a bag. Seats were uncomfortable, but tolerable for 2 hrs."

Pros: "The crew were very friendly."
Cons: "the seats were pretty uncomfortable, that was my main problem with the flight."

Pros: "Price of ticket. Crew was efficient."
Cons: "Baggage limitations are not clear: especially when the ticket says no carryon luggage. What they mean is anything that fits under your seat and is under 20 lbs is OK. Seat did not recline. Leg room was poor."

Cons: "Everything went quickly and smoothly. Great flight; even the weather was less turbulent than expected."

Pros: "Nothing is good on this flight. It was delayed by 7 hours and the communication is not proper"
Cons: "Customer service"

Cons: "Very uncomfortable"

Cons: "They would not refund the charge for a carry on I made in error. I did not have a carry on. Would not give me info as to where I could take my complaint so I guess I took it here. The guy at the desk was HORRIBLE"

Cons: "it was very hard to hear the stewardess"

Pros: "Everything was done right"
Cons: "The landing was rough"

Pros: "The prices are good. That's pretty much it. I can't say anything else"
Cons: "you get what you pay for. Both flights delayed. One delayed for 12 hours. limited days to fly out"

Pros: "All went well. No real disappointments!"
Cons: "A little cramped but not terrible. Would like to know kayak fee up front before booking and all hidden charges!"

Pros: "Smooth timely flight without incident."
Cons: "As retired military we were to have assigned seats since we purchased our tickets but somehow our return tickets separated us by 2 rows & opposite sides of plane. We were supposed to be in an isle seat & a window seat in the same side & row. We do appreciate all Allegiant Air does for the military. Wish all airlines did what they do."

Pros: "Stewardess moved me to a more comfortable seat without me asking."

Pros: "Nothing, honestly. Constantly delayed, cheap airline with forced fees, only one I could take and I can’t believe you exist. You have horrible customer service"
Cons: "I will never fly you again. Sure you don’t care."

Pros: "The flight attendants, the space on the plane, the prompt departure and arrival!"
Cons: "Media has not been reflective of my great experience."

Pros: "Crew was very friendly, very polite unlike the United flights I have taken. I was told the space would be uncomfortable but it was absolutely fine for the short flight."
Cons: "No beverage service. Not even water is offered."

Pros: "Timing was good"
Cons: "Not a glass of water was offered. Who wants alcohol in the morning?"

Cons: "4 hours late. No explanation. I have flown Allegiant 3 times. Late twice."

Pros: "Quick non stop."

Pros: "No Delays All went smooth & arrived early!"

Pros: "After the delay, we were treated to complimentary soft drinks and snack mix. This was after sitting in the plane for over an hour, though."
Cons: "We spent two hours of the delay in the airport and then eventually boarded. However, another problem with the plane developed and we waited for at least an hour more in the incredibly cramped plane. The seats are bearable for a short flight, but they’re hard to endure with multiple delays. The boarding was also disorganized. There were two announcements: one for people who needed extra time to board and another for the final call. Nothing in between."

Cons: "parking my car 2 weeks in Asheville Long term was $96. I should have gone to Charlotte, parked at my friend's house and paid AA the same rate for a nicer seat and cabin leg room. a la carte pricing ran my bill up even with NO checked luggage. Asheville doesn't have a shuttle service for the long-term parking."

Pros: "Could,nt Have went any better."

Pros: "New plane!"
Cons: "Boarded too early!"

Pros: "Excellent value. They had hard time with the head count which delayed our take off. Arrived just a few minutes Late."

Cons: "Lands in South Terminal of Austin’s airport, meaning you have to shuttle 8 miles to get to main terminal or long term parking. Unbelievable! Very inconvenient..."

Pros: "Plane, staff, made best of bad situation. Seats are only OKAY to Good, but NO airlines are really comfortable so by comparison they were good"
Cons: "The delay - this time not due to the airlines, so thus the good review."

Pros: "Direct flight to my Destination"
Cons: "Rental car I paid for on Allegiant website didn't include $50 in airport and sales taxes making it look like the Allegiant rentals were about the same as renting directly from rental car companies. Problem is that Allegiant didn't include taxes in the quote or amount I paid online. Surprise when I got to my destination and was told it would be $50 more. Alamo agent said I wasn't the first person to have that problem. Then on return my bag was damaged and was told I could place a claim at the ticket counter. It would have been helpful to have an agent there or a way to contact an agent. No such luck. After bag charges, poor service and hidden fees Allegiant isn't really a great deal."

Pros: "Fast and efficient!"
Cons: "Everything was great!"

Cons: "Flight was delayed for hours then canceled"

Pros: "No frills inexprnsive"
Cons: "No services"

Pros: "Flew 2 different legs with Allegiant, both of which were delayed for maintenance stuff. 2nd leg, we sat in the plane for an hour waiting for a maintenance guy, so my wife went to the bathroom. No toilet paper! When my wife asked about it, she was told "we won't be getting toilet paper for this flight." Inexpensive is one thing, but...dear lord!"

Cons: "No wifi"

Pros: "Comfort and speed of the flight. Attentive staff!"
Cons: "Need one craft beer"

Pros: "Everything they could control went very well."
Cons: "The flight had a lot of turbulence, but that's not their fault. I thought the pullout handled the situation well."

Cons: "Bad service. Long waits. No directions at airport from the airline and counter service slow"

Pros: "That fact that they did not suply even one free bottle or cup of water is awful. I was very thirsty but did not get a drink because they chaged $2.00 for one bottle of water, and the is just plain wrong."

Pros: "Arrived an hour before flight. Check in took 25 min and tsa 30 minutes. Tried to go through expedite line but agent refused to let me even though flight was leaving in 30 minutes. I have received better treatment in new York airports than here in Myrtle Beach. Who would have thought. There were 3 others that missed the flight. Why would they not just let's be expedited?"
Cons: "See above"

Cons: "No complaints."

Pros: "Great price ."
Cons: "Landing in Austin and having to walk down a wet slippery ramp and then across the tarmac in a thunderstorm ... got VERY wet . How about a cover ?"

Pros: "Flight attendants were very kind."

Read more about Delta

Book cheap flights from Chicago Midway Airport to Maine

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