$81 Find Cheap Flights from Illinois to Maine

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Low seasonJanuary
Cheapest flight$81
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Chicago O'Hare Airport to Boston

FAQs for booking flights from Illinois to Maine

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

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Illinois to Maine.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Maine?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Illinois to Maine is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Illinois to Maine?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Illinois to Maine with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois to Maine?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Illinois to Maine up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines fly most frequently to Maine?

    Illinois and Maine are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (35 flights per week), United Airlines (34 flights per week), and Air New Zealand (31 flights per week).

  • How many airports are there in Maine?

    There are 6 airports in Maine. The busiest airport is Portland Airport (PWM), with 67% of all flights arriving there.

  • Which is the cheapest airport to fly into in Maine?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Maine is Portland Airport (PWM), with an average flight price of $213.

  • What is the cheapest day to fly to Maine?

    Based on KAYAK data, the cheapest day to fly to Maine is Tuesday where round-trip tickets can be as cheap as $302. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $391 on average.

  • What is the cheapest time of day to fly to Maine?

    The cheapest time of day to fly to Maine is generally at night, when round-trip flights cost $301 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Maine is generally in the morning, which is peak travel time and where the average cost of a ticket is $371.

  • What is the cheapest flight to Maine?

    The cheapest ticket to Maine from Illinois found in the last 72 hours was to Portland, at $269 round-trip. The most popular route is Chicago Midway Airport (MDW) to Portland (PWM) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $269.

  • What is the cheapest month to fly from Illinois to Maine?

    The cheapest month for flights from Illinois to Maine is March, when tickets cost $301 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $471 and $414 respectively.

  • How far in advance should I book a flight from Illinois to Maine?

    To get a below average price on the flight from Illinois to Maine, you should book around 4 weeks before departure, which saves you about 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

  • How many cities have direct flights to Maine?

    From Illinois, there are direct flights to Maine from 1 city. This city is Chicago and there are 116 direct flights each week.

  • How many direct flights to Maine are there each day?

    There are around 17 direct flights from within Illinois to Maine every day. Most flights (43%) depart in the evening.

  • How many direct flights to Maine are there each week?

    Each week there are around 116 direct flights from within Illinois to Maine. The most common day for departures is Sunday, with 18% of flights taking off on this day.

  • How long is the flight to Maine?

    An average nonstop flight from Illinois to Maine takes 7h 49m, covering a distance of 1005 miles. The shortest route is Chicago Midway Airport (MDW) to Portland (PWM) with an average flight time of 2h 10m.

  • How many long-haul flights are there to Maine each week?

    There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Maine. Instead, there are 116 short-haul flights (up to 3 hour flight duration), with the most arriving from Chicago.

  • What are the most popular destinations in Maine?

    Based on KAYAK flight searches, the most popular destination is Boston (74% of total searches to Maine). The next most popular destinations are Portland (16%) and Bangor (9%). Searches for flights to Bar Harbor (0%), to Rockland (0%) and to Augusta (0%) are also popular.

Reviews of the top 4 airlines serving from Illinois to Maine

 
Need help choosing which airline to fly with from Illinois to Maine? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4314 reviews
8.1Boarding
7.0Food
7.5Entertainment
8.6Crew
8.0Comfort
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

Everything you need to know for your flight to Maine

Cabin class types available on flights to Illinois

Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.