$79 Find Cheap Flights from Chicago to Maine

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Maine departing on 8/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Maine

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maine, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Maine, as well as popular online travel agencies
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Cheap Flights from Chicago to Maine

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland2 stops$239
Bangor
Bangornonstop$261
Boston
Bostonnonstop$146
Portland
Portland2 stops$239
Bangor
Bangornonstop$261
Boston
Bostonnonstop$146

Book Cheap Chicago to Maine Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Maine that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Maine

Wed, Aug 5 - Wed, Aug 12
JetBlue Logo
10:56 am - 2:23 pm
ORD
-
BOS
2h 27mnonstop
JetBlue Logo
8:10 am - 10:06 am
BOS
-
ORD
2h 56mnonstop
$146JetBlue
Sat, May 30 - Wed, Jun 3
Delta Logo
7:00 am - 10:35 am
ORD
-
BOS
2h 35mnonstop
Delta Logo
5:35 am - 10:16 am
BOS
-
ORD
5h 41m
1 stop
$147Delta
Sat, May 23 - Tue, May 26
American Airlines Logo
7:20 pm - 10:54 pm
ORD
-
BOS
2h 34mnonstop
American Airlines Logo
6:36 pm - 9:00 pm
BOS
-
ORD
3h 24mnonstop
$148American Airlines
Tue, May 19 - Tue, May 26
Southwest Logo
7:45 am - 11:00 am
MDW
-
BOS
2h 15mnonstop
Southwest Logo
7:20 am - 9:05 am
BOS
-
MDW
2h 45mnonstop
$148Southwest
Tue, May 19 - Tue, May 26
Southwest Logo
1:55 pm - 10:20 pm
MDW
-
BOS
7h 25m
1 stop
Southwest Logo
10:45 am - 12:25 pm
BOS
-
MDW
2h 40mnonstop
$149Southwest
Wed, May 13 - Sat, May 16
Multiple Airlines Logo
9:49 am - 1:20 pm
ORD
-
BOS
2h 31mnonstop
Multiple Airlines Logo
12:01 pm - 7:51 pm
BOS
-
ORD
8h 50m
1 stop
$154Multiple Airlines
Thu, Aug 20 - Wed, Aug 26
United Airlines Logo
7:33 am - 11:07 am
ORD
-
BOS
2h 34mnonstop
United Airlines Logo
12:30 pm - 2:21 pm
BOS
-
ORD
2h 51mnonstop
$155United Airlines
Tue, Aug 11 - Tue, Aug 18
United Airlines Logo
6:25 pm - 10:01 pm
ORD
-
PWM
2h 36mnonstop
United Airlines Logo
6:00 am - 7:55 am
PWM
-
ORD
2h 55mnonstop
$242United Airlines
Wed, Aug 19 - Wed, Sep 2
American Airlines Logo
8:03 am - 11:39 am
ORD
-
BGR
2h 36mnonstop
American Airlines Logo
12:09 pm - 2:12 pm
BGR
-
ORD
3h 03mnonstop
$261American Airlines
Fri, May 15 - Fri, May 22
Multiple Airlines Logo
8:30 am - 9:26 am
ORD
-
BGR
23h 56m
1 stop
Multiple Airlines Logo
12:05 pm - 12:23 pm
BGR
-
ORD
25h 18m
1 stop
$264Multiple Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Maine flights

Get data-powered insights and trends into flights from Chicago to Maine to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Maine?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Maine departing in May.

What is the cheapest Chicago to Maine flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Maine from Chicago found in the last 72 hours was to Portland, at $269 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) 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 time of day to fly to Maine?

The average price for all round-trip flights from Chicago to Maine depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

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% cheaper than evening flights, on average. The most expensive time of day to fly to Maine is generally in the evening, which is peak travel time and where the average cost of a ticket is $374.

Can I save money by flying with a layover from Chicago to Maine?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $368, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Maine?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Maine, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Maine is September, when tickets cost $307 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $404 and $397 respectively.

What’s the cheapest day of the week to fly from Chicago to Maine?

The average price of all round-trip flights from Chicago to Maine clicked on KAYAK for each day over the last 12 months.

For Chicago to Maine, Tuesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Maine back to Chicago, the best deals are generally found on Thursday, with Sunday being the most expensive.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Maine, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago 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.

Good to know

Low seasonJanuary
Cheapest flight$79
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Chicago O'Hare Airport to Boston

FAQs - booking Maine flights

  • How does KAYAK find such low prices on flights from Chicago 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 Chicago to Maine.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 Chicago 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 Chicago 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 Chicago 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 Chicago to Maine up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Chicago to Maine

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Maine. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 4327 reviews
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

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

10.0 ExcellentJasmine, Apr 2026
LGB - HNL
Read more Southwest reviews

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 seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

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.

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

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.

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.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

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

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Everything you need to know for your flight from Chicago to Maine

Cabin class types available on flights to Maine

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