$78 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 5/8. 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
Portlandnonstop$269
Bangor
Bangor2 stops$259
Boston
Bostonnonstop$150
Portland
Portlandnonstop$269
Bangor
Bangor2 stops$259
Boston
Bostonnonstop$150

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

Sat, May 23 - Sun, May 24
JetBlue Logo
1:56 pm - 5:27 pm
ORD
-
BOS
2h 31mnonstop
JetBlue Logo
6:00 am - 8:00 am
BOS
-
ORD
3h 00mnonstop
$150JetBlue
Sat, May 2 - Sun, May 3
JetBlue Logo
6:00 am - 9:15 am
ORD
-
BOS
2h 15mnonstop
JetBlue Logo
7:02 am - 8:59 am
BOS
-
ORD
2h 57mnonstop
$151JetBlue
Wed, May 6 - Sat, May 9
Frontier Logo
12:04 pm - 1:24 am
MDW
-
BOS
12h 20m
1 stop
Frontier Logo
12:01 pm - 10:02 pm
BOS
-
MDW
11h 01m
1 stop
$151Frontier
Tue, Apr 28 - Thu, Apr 30
American Airlines Logo
5:39 pm - 9:12 pm
ORD
-
BOS
2h 33mnonstop
American Airlines Logo
6:30 am - 8:44 am
BOS
-
ORD
3h 14mnonstop
$155American Airlines
Sat, May 9 - Sat, May 16
Southwest Logo
6:05 pm - 9:25 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
7:15 am - 9:05 am
BOS
-
MDW
2h 50mnonstop
$167Southwest
Sat, May 9 - Sun, May 10
Southwest Logo
7:45 am - 11:00 am
MDW
-
BOS
2h 15mnonstop
Southwest Logo
6:10 am - 7:55 am
BOS
-
MDW
2h 45mnonstop
$172Southwest
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
Wed, Aug 19 - Wed, Sep 2
Delta Logo
5:30 am - 4:01 pm
ORD
-
BGR
9h 31m
2 stops
Delta Logo
4:50 pm - 10:43 pm
BGR
-
ORD
6h 53m
1 stop
$286Delta
Tue, Jun 2 - Thu, Jun 11
Delta Logo
6:30 pm - 12:43 am
ORD
-
PWM
5h 13m
1 stop
Delta Logo
6:57 pm - 11:59 pm
PWM
-
ORD
6h 02m
1 stop
$289Delta
Sun, Jul 19 - Wed, Jul 22
United Airlines Logo
6:08 pm - 9:41 pm
ORD
-
PWM
2h 33mnonstop
United Airlines Logo
6:00 am - 8:00 am
PWM
-
ORD
3h 00mnonstop
$296United 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 June.

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 $249 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 $249.

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 2% 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 $375.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $368 on average.

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 Sunday is the most expensive. Flying from Maine back to Chicago, the best deals are generally found on Wednesday, 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 21% 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$77
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 Midway 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 4328 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
Airline reviews

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

10.0 ExcellentAnonymous, Apr 2026
LAS - OKC
Read more Southwest reviews

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.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

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)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

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.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

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.