$69 Find Cheap Flights from Chicago Midway Airport 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 Midway to Maine departing on 4/9. 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 Midway to Maine

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Bostonnonstop$127
Bangor
Bangor2 stops$430
Portland
Portland1 stop$229
Boston
Bostonnonstop$127
Bangor
Bangor2 stops$430
Portland
Portland1 stop$229

Book Cheap Midway 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 Midway 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 Midway to Maine

Wed, Mar 25 - Wed, Apr 1
Southwest Logo
6:10 pm - 9:25 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
2:00 pm - 3:45 pm
BOS
-
MDW
2h 45mnonstop
$127Southwest
Sat, Apr 4 - Tue, Apr 7
Southwest Logo
4:35 pm - 11:55 pm
MDW
-
BOS
6h 20m
1 stop
Southwest Logo
2:25 pm - 4:05 pm
BOS
-
MDW
2h 40mnonstop
$130Southwest
Wed, Apr 8 - Wed, Apr 15
Southwest Logo
6:00 pm - 9:20 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
7:20 am - 9:05 am
BOS
-
MDW
2h 45mnonstop
$132Southwest
Sat, Mar 28 - Thu, Apr 2
Southwest Logo
6:45 pm - 10:00 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
7:15 am - 9:10 am
BOS
-
MDW
2h 55mnonstop
$133Southwest
Tue, Mar 24 - Tue, Mar 31
Southwest Logo
2:35 pm - 5:45 pm
MDW
-
BOS
2h 10mnonstop
Southwest Logo
6:00 pm - 7:50 pm
BOS
-
MDW
2h 50mnonstop
$137Southwest
Sat, Apr 4 - Sat, Apr 11
Southwest Logo
4:35 pm - 11:55 pm
MDW
-
BOS
6h 20m
1 stop
Southwest Logo
7:15 am - 9:05 am
BOS
-
MDW
2h 50mnonstop
$146Southwest
Thu, Apr 9 - Mon, Apr 13
Delta Logo
9:35 am - 4:06 pm
MDW
-
PWM
5h 31m
1 stop
Delta Logo
12:46 pm - 5:58 pm
PWM
-
MDW
6h 12m
1 stop
$233Delta
Tue, Mar 24 - Tue, Mar 31
Delta Logo
1:10 pm - 11:12 pm
MDW
-
PWM
9h 02m
2 stops
Delta Logo
12:51 pm - 5:54 pm
PWM
-
MDW
6h 03m
1 stop
$245Delta
Thu, Mar 19 - Sun, Mar 22
Multiple Airlines Logo
2:41 pm - 6:14 pm
MDW
-
BGR
26h 33m
2 stops
Multiple Airlines Logo
7:53 pm - 2:21 pm
BGR
-
MDW
19h 28m
1 stop
$430Multiple Airlines
Thu, May 21 - Sun, May 24
Delta Logo
6:30 am - 4:24 pm
MDW
-
BGR
8h 54m
2 stops
Delta Logo
6:00 am - 12:42 pm
BGR
-
MDW
7h 42m
2 stops
$529Delta
Booking Insights

KAYAK's insights & trends for Midway to Maine flights

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

What is the cheapest Chicago Midway Airport 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 Midway Airport found in the last 72 hours was to Portland, at $434 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Portland (PWM), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $434.

Can I save money by flying with a layover from Chicago Midway Airport 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 1 stop layover the cheapest option at $410 on average.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport 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 Midway Airport to Maine is July, when tickets cost $247 (return) on average. On the other hand, the most expensive months are January and February, when the average cost of round-trip tickets is $414 and $321 respectively.

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

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

Your flight ticket price will generally be cheaper if you fly to Maine on a Saturday and more expensive on a Sunday. On your return trip to Chicago Midway Airport, you should consider flying back on a Wednesday, and avoid Sundays for better deals.

How far in advance should I book a flight from Chicago Midway Airport 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 Midway Airport 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 Midway Airport to Maine, you should book around 3 weeks before departure, which saves you about 43% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$69
Best time to beat the crowds but there is an average 42% increase in price.
Most popular time to fly with an average 6% increase in price.
Flight from Chicago Midway Airport to Boston

FAQs - booking Maine flights

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

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

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

  • What is the cheapest time of day to fly to Maine?

    The cheapest time of day to fly to Maine is generally in the evening, when round-trip flights cost $211 on average. Morning departures are around 20% more expensive than evening flights, on average. 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 $253.

Reviews of the top airline flying from Midway 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 Midway 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 4300 reviews
8.1Boarding
8.6Crew
7.0Food
7.5Entertainment
8.0Comfort
Airline reviews

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

10.0 ExcellentTy&Steph, Feb 2026
CLT - STL
Read more Southwest reviews

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)