$88 Find Cheap Flights from Illinois to Maine

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Good to know

Low seasonJanuary
Cheapest flight$84
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 11% 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 (27 flights per week), United Airlines (22 flights per week), and Air New Zealand (21 flights per week).

  • How many airports are there in Maine?

    There are 6 airports in Maine. The busiest airport is Portland Airport (PWM), with 65% 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 $203.

  • 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 $311. 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 $304 on average. Morning departures are around 1% more expensive than evening flights, on average. 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 $372.

  • What is the cheapest flight to Maine?

    The cheapest ticket to Maine from Illinois found in the last 72 hours was to Portland, at $268 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 $268.

  • 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 $408 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 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 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 84 direct flights each week.

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

    There are around 12 direct flights from within Illinois to Maine every day. Most flights (35%) depart in the morning.

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

    Each week there are around 84 direct flights from within Illinois to Maine. The most common day for departures is Sunday, with 15% of flights taking off on this day.

  • How long is the flight to Maine?

    An average nonstop flight from Illinois to Maine takes 7h 38m, covering a distance of 1005 miles. The shortest route is Chicago Midway Airport (MDW) to Boston (BOS) 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 84 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 (72% of total searches to Maine). The next most popular destinations are Portland (19%) and Bangor (9%). Searches for flights to Bar Harbor (0%), to Rockland (0%) and to Augusta (0%) are also popular.

Reviews of the top 3 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 4299 reviews
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

2.0 MediocreAnonymous, May 2026
MCO - MDW
Read more Southwest reviews

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

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.

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.

Pretty awful. 2 hours late due to operational issues and finally deboarded around 2am.

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.

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.