$130 Find Cheap Flights from Chicago to Maine - Compare and Save

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Cheap Flights from Chicago to Maine

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Bangor
2h 41mNonstop
from $341per person
Portland
2h 17mNonstop
from $349per person
Augusta
24h 35m2 stops
from $613per person
Booking Insights

Price, demand and travel trends for Chicago to Maine flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Chicago to Maine recently?

The cheapest fares from Chicago to Maine on KAYAK in the last week were to Bangor (BGR) from $341 round-trip and to Portland (PWM) from $349 round-trip.

How do fares into airports in Maine compare?

According to KAYAK data from the last 12 months, the cheapest airports to fly into Maine from Chicago are:

• Portland (PWM) (avg. price $384)
• Bangor (BGR) (avg. price $395)
• Augusta (AUG) (avg. price $483)

What's the cheapest month to fly from Chicago to Maine?

April is typically the cheapest month to fly from Chicago to Maine, with round-trip fares averaging $319. December and November are usually the most expensive, averaging $507 and $441, respectively.

How do fares from Chicago to Maine vary by day of the week?

On average, Saturday is the cheapest day to fly from Chicago to Maine and Sunday is the most expensive. Looking at the past 12 months of KAYAK data, it's 27% more expensive to fly on a Sunday compared to Saturday.

What's the best time of day to fly from Chicago to Maine?

It's cheapest to fly to Maine in the afternoon with average prices of $355. The morning is the most expensive time to fly, with average prices of $411.

What's the best time to book a flight from Chicago to Maine?

Book your flights 13 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 26% compared to booking at the last minute (within 2 weeks of departure).

Key details for Chicago to Maine flights

Low season

December

Cheapest flight

$130
Beat the crowds with an average 72% drop in travelers.
The most popular month to fly with an average 90% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to Portland

Your Chicago to Maine flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Chicago to Maine?

    Fares from Chicago to Maine are around their usual level right now. A round-trip under $315 is considered a good deal, so it's worth keeping an eye out, or setting a Price Alert to catch fare changes.

  • How much should I budget for a flight from Chicago to Maine?

    Over the past 12 months, round-trip fares from Chicago to Maine have typically cost between $315 and $481.

  • What are the main airports serving Maine?

    There are 7 airports in Maine. 73% of KAYAK users choose Portland (PWM) as their arrival airport, while 27% choose Bangor (BGR).

  • Which airlines fly nonstop from Chicago to Maine?

    Based on the flight schedule for the next 3 months, 2 airlines offer nonstop flights on this route:

    • United Airlines
    • American Airlines

  • Which destinations in Maine can I fly nonstop from Chicago?

    Based on the flight schedule for the next 3 months, you can fly nonstop from Chicago to just one destination in Maine: Portland.

  • Is it cheaper to fly with a layover from Chicago to Maine?

    Yes, nonstop flights from Chicago to Maine average $388 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • New York John F Kennedy Intl (JFK) (avg. price $304)
    • Atlanta Hartsfield-Jackson (ATL) (avg. price $379)
    • Washington, D.C. Dulles Intl (IAD) (avg. price $380)

  • How long is a flight from Chicago to Maine?

    Nonstop flights from Chicago to Maine take 2h 37m on average. All flights fly into Portland (PWM).

  • Which cabin classes are available from Chicago to Maine?

    On flights from Chicago to Maine you can book Economy Class or First Class.

  • What are the earliest and latest flights from Chicago to Maine?

    The earliest nonstop flight from Chicago to Maine departs at 8:00 am and the latest leaves at 6:50 pm. Nonstop flights take about 2h 37m.

Your guide to booking Chicago to Maine flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 13 weeks before your trip. KAYAK data shows fares in this window are around 26% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • Flexible with your dates? Fly in April to save some money. It's typically the cheapest month on this route, while flights in December will cost you the most.
  • Fly out on a Saturday to get the cheapest fares. Avoid Sunday flights, which are about 27% more expensive.
  • If you're watching your budget, fly into Portland (PWM) which has the lowest average airfare in the region. Just remember to budget for any onward travel by bus, car or domestic flight.
  • Start your trip in Portland, the most popular destination in Maine. From there, it's easy to continue on to other popular spots such as Bar Harbor, Ogunquit and Old Orchard Beach.
  • Whether you're trying to save time or money, Portland (PWM) is usually your best option from Chicago.

Reviews of the top 3 airlines serving from Chicago to Maine

 
Need help choosing which airline to fly with from Chicago 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 4222 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

8.0 ExcellentEmmalee, Oct 2026
Read more Southwest reviews

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack

I like the staff members they were super nice and helpful very sweet people :)

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Very uncomfortable and cramped seats. Everything else was okay, the crew members were nice but nothing was exceptional.

Waited on tarmac for approximately 15-25 minutes before taking off. When landing, the time it took to taxi to our gate was the also 15-25 minutes.

Connection times always good online, but not in reality when first leg is delayed (2 out of 2 times this trip).

It was good flight was smooth, little cold on the plane but other wise good.

Great flight and crew. Need more legroom and DO NOT allow seats to recline.

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

The TVs on the plane were all broken and inoperable. No snacks or food were served. Plane was very old and uncomfortable.

Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

The seats are very small, that is all the staff did a good job.

All good. Flight crew was super friendly at the end of a long day

The food in first class has taken a big downturn

Flight was fine. Just delays leaving due to mechanical issues. But flight crew were kind and professional. Seats were spacious. American doesn't need to have 9 groups for boarding.

Both departure and return flights had mechanical delays. Their planes are antiquated resulting in a two hour flight taking almost four hours to complete.

Crew were helpful, pilot kept us informed about turbulence, snack choice was awesome!

It was one of the worst I have ever had. The plane was over booked, and I did not have a seat. When I questioned why because I had booked this weeks in advance. I was brushed off to be advised they are trying to find someone to give up their seat. Only to be advised I would be boarding last. I had priority boarding in group 1-4. When I asked why I had to be last because that is not what I paid for I was advised it doesn't matter you will get a seat. The ticket person was very rude and unprofessional. The gate changed several times and it was going from one area to another area far away from where we were at. I feel like I should have been compensated in some kind of way because of the way I was treated. The ticket agent acted like it was my fault that the plane was over booked. Not one time was I apologized to for this inconvenience.

I have posted the comments in the first flight leg.

First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.

My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.

The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.

More options for your flight from Chicago to Maine

Complete your trip to Maine with a hotel stay or car rental