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Flight Deals
Cheap Flights from Chicago to Maine
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysBook 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, Feb 3 - Thu, Feb 11
11:00 am - 2:44 pmORD Chicago O'Hare Intl-PWM Portland
2h 44mnonstop
7:49 am - 10:00 amPWM Portland-ORD Chicago O'Hare Intl
3h 11mnonstop
$289United Airlines
Tue, Feb 2 - Thu, Feb 11
11:00 am - 2:44 pmORD Chicago O'Hare Intl-PWM Portland
2h 44mnonstop
7:49 am - 10:00 amPWM Portland-ORD Chicago O'Hare Intl
3h 11mnonstop
$289United Airlines
Wed, Feb 3 - Thu, Feb 11
2:56 pm - 9:43 pmORD Chicago O'Hare Intl-PWM Portland
5h 47m1 stop Washington, D.C. Reagan-National
12:15 pm - 2:31 pmPWM Portland-ORD Chicago O'Hare Intl
3h 16mnonstop
$299American Airlines
Tue, Feb 2 - Thu, Feb 11
10:30 am - 6:53 pmORD Chicago O'Hare Intl-PWM Portland
7h 23m1 stop Newark
7:49 am - 10:00 amPWM Portland-ORD Chicago O'Hare Intl
3h 11mnonstop
$299United Airlines
Wed, Feb 3 - Thu, Feb 11
2:26 pm - 9:03 pmORD Chicago O'Hare Intl-PWM Portland
5h 37m1 stop Newark
7:10 am - 1:15 pmPWM Portland-ORD Chicago O'Hare Intl
7h 05m1 stop Newark
$309United Airlines
Wed, Nov 25 - Fri, Dec 4
3:59 pm - 11:31 pmORD Chicago O'Hare Intl-PWM Portland
6h 32m1 stop Atlanta Hartsfield-Jackson
4:00 pm - 9:36 pmPWM Portland-ORD Chicago O'Hare Intl
6h 36m1 stop New York John F Kennedy Intl
$334Delta
Wed, Nov 25 - Fri, Dec 4
3:59 pm - 11:31 pmORD Chicago O'Hare Intl-PWM Portland
6h 32m1 stop Atlanta Hartsfield-Jackson
12:49 pm - 7:45 pmPWM Portland-ORD Chicago O'Hare Intl
7h 56m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$339Delta
Wed, Feb 3 - Thu, Feb 11
1:54 pm - 11:10 pmORD Chicago O'Hare Intl-PWM Portland
8h 16m2 stops Detroit Metropolitan Wayne County New York LaGuardia
6:00 am - 11:19 amPWM Portland-ORD Chicago O'Hare Intl
6h 19m1 stop New York LaGuardia
$339Delta
Wed, Nov 25 - Fri, Dec 4
2:52 pm - 10:39 pmORD Chicago O'Hare Intl-PWM Portland
6h 47m1 stop Washington, D.C. Reagan-National
12:44 pm - 3:00 pmPWM Portland-ORD Chicago O'Hare Intl
3h 16mnonstop
$349American Airlines
Fri, Dec 4 - Sun, Dec 6
5:00 pm - 11:49 pmORD Chicago O'Hare Intl-PWM Portland
5h 49m1 stop Washington, D.C. Reagan-National
12:44 pm - 3:00 pmPWM Portland-ORD Chicago O'Hare Intl
3h 16mnonstop
$349American Airlines
Recent one-way flight deals from Chicago to Maine
Fri, Dec 11
8:26 am - 11:58 amORD Chicago O'Hare Intl-PWM Portland
2h 32mnonstop
$145American Airlines
Thu, Feb 11
8:10 am - 11:45 amORD Chicago O'Hare Intl-PWM Portland
2h 35mnonstop
$145American Airlines
Wed, Dec 9
8:26 am - 11:58 amORD Chicago O'Hare Intl-PWM Portland
2h 32mnonstop
$145American Airlines
Fri, Dec 11
6:10 pm - 11:55 pmMDW Chicago Midway-PWM Portland
4h 45m1 stop Baltimore/Washington
$155Southwest
Wed, Dec 9
8:50 am - 4:39 pmORD Chicago O'Hare Intl-PWM Portland
6h 49m1 stop New York LaGuardia
$155Delta
Fri, Feb 5
3:00 pm - 11:26 pmORD Chicago O'Hare Intl-PWM Portland
7h 26m1 stop Atlanta Hartsfield-Jackson
$155Delta
Wed, Jan 13
9:56 am - 4:16 pmORD Chicago O'Hare Intl-PWM Portland
5h 20m1 stop Washington, D.C. Reagan-National
$155American Airlines
Wed, Nov 25
6:18 pm - 9:51 pmORD Chicago O'Hare Intl-PWM Portland
2h 33mnonstop
$177United Airlines
Fri, Dec 25
11:59 am - 3:31 pmORD Chicago O'Hare Intl-PWM Portland
2h 32mnonstop
$177United Airlines
Wed, Nov 25
6:18 pm - 9:51 pmORD Chicago O'Hare Intl-PWM Portland
2h 33mnonstop
$177United Airlines
Recent last minute flight deals from Chicago to Maine
Tue, Nov 10 - Tue, Nov 17
6:18 pm - 9:51 pmORD Chicago O'Hare Intl-PWM Portland
2h 33mnonstop
5:08 pm - 7:05 pmPWM Portland-ORD Chicago O'Hare Intl
2h 57mnonstop
$399United Airlines
Tue, Nov 10 - Tue, Nov 17
3:36 pm - 11:21 pmORD Chicago O'Hare Intl-PWM Portland
6h 45m1 stop Newark
5:08 pm - 7:05 pmPWM Portland-ORD Chicago O'Hare Intl
2h 57mnonstop
$409United Airlines
Tue, Nov 10 - Tue, Nov 17
4:51 pm - 10:29 pmORD Chicago O'Hare Intl-PWM Portland
4h 38m1 stop Washington, D.C. Reagan-National
6:00 am - 11:04 amPWM Portland-ORD Chicago O'Hare Intl
6h 04m1 stop Philadelphia
$419American Airlines
Fri, Nov 6 - Sun, Nov 8
8:25 am - 11:53 amORD Chicago O'Hare Intl-PWM Portland
2h 28mnonstop
12:50 pm - 3:00 pmPWM Portland-ORD Chicago O'Hare Intl
3h 10mnonstop
$419American Airlines
Sat, Nov 7 - Tue, Nov 10
6:15 pm - 9:48 pmORD Chicago O'Hare Intl-PWM Portland
2h 33mnonstop
5:08 pm - 7:05 pmPWM Portland-ORD Chicago O'Hare Intl
2h 57mnonstop
$419United Airlines
Fri, Nov 6 - Tue, Nov 10
6:18 pm - 9:52 pmORD Chicago O'Hare Intl-PWM Portland
2h 34mnonstop
8:47 am - 10:47 amPWM Portland-ORD Chicago O'Hare Intl
3h 00mnonstop
$419United Airlines
Tue, Nov 10 - Tue, Nov 17
7:05 am - 4:38 pmORD Chicago O'Hare Intl-PWM Portland
8h 33m2 stops Detroit Metropolitan Wayne County New York LaGuardia
2:05 pm - 7:05 pmPWM Portland-ORD Chicago O'Hare Intl
6h 00m1 stop Atlanta Hartsfield-Jackson
$424Delta
Tue, Nov 10 - Tue, Nov 17
8:29 am - 4:38 pmORD Chicago O'Hare Intl-PWM Portland
7h 09m2 stops Detroit Metropolitan Wayne County New York LaGuardia
4:50 pm - 11:54 pmPWM Portland-ORD Chicago O'Hare Intl
8h 04m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$429Delta
Thu, Nov 5 - Mon, Nov 9
8:25 am - 11:53 amORD Chicago O'Hare Intl-PWM Portland
2h 28mnonstop
4:10 pm - 11:30 pmPWM Portland-ORD Chicago O'Hare Intl
8h 20m1 stop Washington, D.C. Reagan-National
$429American Airlines
Sat, Nov 7 - Wed, Nov 11
6:10 am - 1:51 pmORD Chicago O'Hare Intl-PWM Portland
6h 41m1 stop New York John F Kennedy Intl
6:00 am - 12:20 pmPWM Portland-ORD Chicago O'Hare Intl
7h 20m1 stop Atlanta Hartsfield-Jackson
$439Delta
Recent direct flight deals from Chicago to Maine
Wed, Feb 3 - Thu, Feb 11
11:00 am - 2:44 pmORD Chicago O'Hare Intl-PWM Portland
2h 44mnonstop
7:49 am - 10:00 amPWM Portland-ORD Chicago O'Hare Intl
3h 11mnonstop
$289United Airlines
Tue, Feb 2 - Thu, Feb 11
11:00 am - 2:44 pmORD Chicago O'Hare Intl-PWM Portland
2h 44mnonstop
7:49 am - 10:00 amPWM Portland-ORD Chicago O'Hare Intl
3h 11mnonstop
$289United Airlines
Fri, Dec 4 - Sun, Dec 6
8:26 am - 11:58 amORD Chicago O'Hare Intl-PWM Portland
2h 32mnonstop
12:44 pm - 3:00 pmPWM Portland-ORD Chicago O'Hare Intl
3h 16mnonstop
$349American Airlines
Thu, Feb 11 - Mon, Feb 15
8:10 am - 11:45 amORD Chicago O'Hare Intl-PWM Portland
2h 35mnonstop
12:15 pm - 2:31 pmPWM Portland-ORD Chicago O'Hare Intl
3h 16mnonstop
$359American Airlines
Thu, Nov 19 - Sun, Nov 22
6:18 pm - 9:51 pmORD Chicago O'Hare Intl-PWM Portland
2h 33mnonstop
8:47 am - 10:47 amPWM Portland-ORD Chicago O'Hare Intl
3h 00mnonstop
$359United Airlines
Tue, Nov 24 - Fri, Nov 27
6:18 pm - 9:51 pmORD Chicago O'Hare Intl-PWM Portland
2h 33mnonstop
8:29 am - 10:29 amPWM Portland-ORD Chicago O'Hare Intl
3h 00mnonstop
$359United Airlines
Fri, Nov 20 - Fri, Nov 27
6:18 pm - 9:52 pmORD Chicago O'Hare Intl-PWM Portland
2h 34mnonstop
8:29 am - 10:29 amPWM Portland-ORD Chicago O'Hare Intl
3h 00mnonstop
$359United Airlines
Mon, Nov 23 - Sat, Dec 5
8:29 am - 11:56 amORD Chicago O'Hare Intl-PWM Portland
2h 27mnonstop
12:34 pm - 2:50 pmPWM Portland-ORD Chicago O'Hare Intl
3h 16mnonstop
$359American Airlines
Thu, Dec 24 - Thu, Dec 31
6:50 pm - 10:45 pmORD Chicago O'Hare Intl-PWM Portland
2h 55mnonstop
4:28 pm - 6:40 pmPWM Portland-ORD Chicago O'Hare Intl
3h 12mnonstop
$369United Airlines
Mon, Nov 23 - Sat, Dec 5
8:29 am - 11:56 amORD Chicago O'Hare Intl-PWM Portland
2h 27mnonstop
12:34 pm - 2:50 pmPWM Portland-ORD Chicago O'Hare Intl
3h 16mnonstop
$369American 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.
Prices
Airlines
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 November.
Flight prices are typical for this route right now.
Flights to Maine from Chicago usually cost between $326 and $505 in November.The lowest price found in the past 5 days was $334 on Delta (Nov 25-Dec 4).
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 5 days was to Portland, at $307 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 5 days was $307.
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 $312 on average. Morning departures are around 4% 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 $410.
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 April, when tickets cost $334 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $481 and $463 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, Wednesday 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 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.
Which airlines fly non-stop between Chicago and Maine?
Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Chicago to Maine.
There are 2 airlines that fly nonstop from Chicago to Maine. They are American Airlines and United Airlines. The cheapest airline for this route is American Airlines, with the best round-trip deal found costing $229 and arriving in Portland (PWM). On average, American Airlines offers the best prices for nonstop flights between Chicago and Maine.
Which airlines fly most frequently between Chicago and Maine?
Air New Zealand connects Chicago to Maine with 14 flights per week. United Airlines also offers 14 flights per week, while American Airlines follows with 7 flights per week.
How long does a flight from Chicago to Maine take?
The duration of a flight to Maine depends on your arrival airport. The shortest routes to Maine from Chicago are to Portland, which takes 3h 21m, and Bangor, which takes 5h 49m.
Which cabin class options are there for flights between Chicago and Maine?
The average price of round-trip flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.
What’s the earliest departure time from Chicago to Maine?
The earliest flight from Chicago to Maine departs at 8:00 am, landing in Portland at 11:28 am.
What’s the latest departure time from Chicago to Maine?
If you prefer to fly at night, the latest flight from Chicago to Maine jets off at 6:18 pm and lands in Portland at 9:51 pm.
Good to know
Low season | January |
|---|---|
High season | July |
Cheapest flight | $145 |
FAQs - booking Maine flights
Reviews of the top 3 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.
8.0
SouthwestOverall score based on 4214 reviews
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
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
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.
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.
It was great. The staff is always helpful and polite. The app is great and makes the whole trip and process so easy. They even offer a step to step guide to your correct terminal. And they keep all the information you'll need updated. Anything you can think of! Great experience.
Price was crazy watch it if you Chan he your flight
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.
DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.
AA was fine....the overall experience was subpar, but not due to the airline due to broader issues
More options for your flight from Chicago to Maine
Complete your trip to Maine with a hotel stay or car rental
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.
Flights from other airports in Chicago to Maine
Flights from all airports in Chicago to Maine. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from Chicago to popular cities in Maine
Flights from Chicago to Bangorfrom $379
Flights from Chicago to Bostonfrom $185
Flights from Chicago to Portlandfrom $289