$88 Find Cheap Flights from Chicago to Maine - Compare and Save

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 9/2. 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.
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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$277
Bangor
Bangor1 stop$291
Boston
Boston1 stop$166
Portland
Portland2 stops$277
Bangor
Bangor1 stop$291
Boston
Boston1 stop$166

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, Sep 5 - Sun, Sep 6
Frontier Logo
7:44 pm - 9:09 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
12h 25m1 stop Orlando
Frontier Logo
12:45 pm - 8:04 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
8h 19m1 stop Atlanta Hartsfield-Jackson
$166Frontier
Tue, Oct 20 - Tue, Oct 27
Frontier Logo
9:33 pm - 10:52 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
12h 19m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:35 pm - 7:44 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
8h 09m1 stop Atlanta Hartsfield-Jackson
$166Frontier
Sat, Sep 19 - Sat, Sep 26
JetBlue Logo
9:38 am - 1:06 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 28mnonstop
JetBlue Logo
7:00 am - 8:48 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 48mnonstop
$204JetBlue
Sat, Sep 26 - Sat, Oct 3
JetBlue Logo
8:24 pm - 12:09 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 45mnonstop
JetBlue Logo
7:00 am - 8:48 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 48mnonstop
$205JetBlue
Wed, Sep 30 - Sat, Oct 3
United Airlines Logo
9:05 am - 12:48 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 43mnonstop
United Airlines Logo
12:45 pm - 2:37 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 52mnonstop
$207United Airlines
Wed, Sep 23 - Sat, Sep 26
United Airlines Logo
1:55 pm - 5:36 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 41mnonstop
United Airlines Logo
7:01 am - 9:00 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 59mnonstop
$207United Airlines
Sat, Sep 12 - Tue, Sep 15
Southwest Logo
11:25 am - 2:45 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 20mnonstop
Southwest Logo
10:05 am - 11:35 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 30mnonstop
$207Southwest
Tue, Sep 29 - Sat, Oct 3
Southwest Logo
6:40 am - 9:55 amMDW  Chicago Midway-BOS Boston Logan Intl
2h 15mnonstop
Southwest Logo
7:40 am - 9:15 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 35mnonstop
$207Southwest
Sat, Sep 19 - Sat, Sep 26
Delta Logo
7:30 am - 11:01 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 31mnonstop
Delta Logo
1:35 pm - 3:26 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 51mnonstop
$207Delta
Wed, Sep 23 - Sat, Sep 26
Delta Logo
10:29 am - 2:05 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 36mnonstop
Delta Logo
7:30 am - 9:24 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 54mnonstop
$207Delta
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 October.

Flight prices are below average for this route right now.

Flights to Maine from Chicago usually cost between $307 and $455 in October.
The lowest price found in the past 5 days was $277 on Southwest (Oct 27-Oct 30).

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 $271 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 $271.

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 in the afternoon, when round-trip flights cost $312 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Maine is generally in the morning, which is peak travel time and where the average cost of a ticket is $384.

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 March, when tickets cost $317 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $438 and $431 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, Saturday 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 3 weeks before departure, which saves you about 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low season

January

Cheapest flight

$88
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 14% increase in price.
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 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.
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 4218 reviews
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
Airline reviews

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.

10.0 ExcellentDenis, Aug 2026
Read more Southwest reviews

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.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

gate crew was courteous and helpful, flight attendant was nice and friendly once we got going. But we pushed off from the gate relatively on time, then sat there like 10 ft away, for an hour, with no announcement or explanation. Taxiing then took forever, and I get that there was runway congestion, but would be helpful to keep us posted on whats going on

The power outlets were not working for my row. Also felt like the seats have gotten smaller. I was in the window seat and felt like suffocated, as the two passengers next to me were tall and wide.

Terrible. The flight I booked had a convenient departure time. Quick layover. And an arrival timed that worked for the people who had to pick me up. Thanks to delays and rebooking I got none of those things

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

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.