$68 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 4/15. 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
Portland1 stop$231
Bangor
Bangornonstop$261
Boston
Bostonnonstop$135
Portland
Portland1 stop$231
Bangor
Bangornonstop$261
Boston
Bostonnonstop$135

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, Apr 22 - Wed, Apr 29
Delta Logo
6:00 am - 9:26 am
ORD
-
BOS
2h 26mnonstop
Delta Logo
4:55 pm - 6:59 pm
BOS
-
ORD
3h 04mnonstop
$135Delta
Tue, Apr 21 - Wed, Apr 22
Southwest Logo
12:45 pm - 4:05 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
6:20 pm - 8:10 pm
BOS
-
MDW
2h 50mnonstop
$135Southwest
Thu, Apr 30 - Mon, May 4
JetBlue Logo
6:00 am - 9:15 am
ORD
-
BOS
2h 15mnonstop
JetBlue Logo
7:02 am - 8:59 am
BOS
-
ORD
2h 57mnonstop
$137JetBlue
Tue, Apr 21 - Tue, Apr 28
Multiple Airlines Logo
6:08 pm - 1:31 am
ORD
-
BOS
6h 23m
1 stop
Multiple Airlines Logo
7:35 pm - 9:39 pm
BOS
-
ORD
3h 04mnonstop
$138Multiple Airlines
Thu, Apr 30 - Mon, May 4
JetBlue Logo
9:49 am - 1:15 pm
ORD
-
BOS
2h 26mnonstop
JetBlue Logo
7:35 pm - 9:36 pm
BOS
-
ORD
3h 01mnonstop
$141JetBlue
Tue, Apr 21 - Mon, Apr 27
Multiple Airlines Logo
9:41 am - 1:07 pm
ORD
-
BOS
2h 26mnonstop
Multiple Airlines Logo
12:31 pm - 11:01 pm
BOS
-
ORD
11h 30m
1 stop
$143Multiple Airlines
Tue, Apr 21 - Thu, Apr 23
United Airlines Logo
11:17 am - 2:48 pm
ORD
-
BOS
2h 31mnonstop
United Airlines Logo
9:20 am - 11:20 am
BOS
-
ORD
3h 00mnonstop
$145United Airlines
Fri, Apr 10 - Tue, Apr 14
United Airlines Logo
6:00 am - 9:25 am
ORD
-
BOS
2h 25mnonstop
United Airlines Logo
11:00 am - 12:59 pm
BOS
-
ORD
2h 59mnonstop
$147United Airlines
Wed, Aug 19 - Wed, Sep 2
American Airlines Logo
1:01 pm - 4:43 pm
ORD
-
BGR
2h 42mnonstop
American Airlines Logo
12:09 pm - 2:12 pm
BGR
-
ORD
3h 03mnonstop
$261American Airlines
Wed, Aug 19 - Wed, Sep 2
American Airlines Logo
1:01 pm - 4:43 pm
ORD
-
BGR
2h 42mnonstop
American Airlines Logo
7:00 am - 12:14 pm
BGR
-
ORD
6h 14m
1 stop
$271American 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 $209 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 $209.

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 $300 on average. Morning departures are around 3% 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 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 5 weeks before departure, which saves you about 27% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$68
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 4% 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 4331 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

2.0 MediocreStuart, Mar 2026
HOU - STL
Read more Southwest reviews

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

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.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

It was fine. 55 minute flight. No snacks or beverage service offered. Boarding went smoothly and my walker was waiting for me on the jet way.

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

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

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.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

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.