$66 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 2/18. 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
Portland
Portland2 stops$240
Bangor
Bangor2 stops$422
Boston
Boston1 stop$132
Portland
Portland2 stops$240
Bangor
Bangor2 stops$422
Boston
Boston1 stop$132

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

Sat, Feb 7 - Sun, Feb 8
Southwest Logo
6:25 am - 12:20 pm
MDW
-
BOS
4h 55m
1 stop
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
$132Southwest
Tue, Feb 17 - Wed, Feb 25
Frontier Logo
6:00 am - 1:13 am
MDW
-
BOS
18h 13m
1 stop
Frontier Logo
6:00 am - 7:07 pm
BOS
-
MDW
14h 07m
1 stop
$134Frontier
Tue, Feb 17 - Fri, Feb 27
Frontier Logo
6:00 am - 1:13 am
MDW
-
BOS
18h 13m
1 stop
Frontier Logo
6:00 am - 6:38 pm
BOS
-
MDW
13h 38m
1 stop
$135Frontier
Sat, Feb 14 - Sat, Feb 21
Southwest Logo
2:10 pm - 11:00 pm
MDW
-
BOS
7h 50m
1 stop
Southwest Logo
5:15 am - 7:00 am
BOS
-
MDW
2h 45mnonstop
$136Southwest
Mon, Feb 16 - Mon, Feb 23
Southwest Logo
6:05 am - 9:25 am
MDW
-
BOS
2h 20mnonstop
Southwest Logo
5:20 am - 7:10 am
BOS
-
MDW
2h 50mnonstop
$137Southwest
Mon, Feb 16 - Wed, Feb 18
Southwest Logo
6:05 am - 9:25 am
MDW
-
BOS
2h 20mnonstop
Southwest Logo
1:20 pm - 6:35 pm
BOS
-
MDW
6h 15m
2 stops
$138Southwest
Sat, Feb 7 - Sun, Feb 8
Southwest Logo
6:25 am - 12:20 pm
MDW
-
BOS
4h 55m
1 stop
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
$141Southwest
Tue, Feb 17 - Thu, Feb 19
Southwest Logo
6:35 pm - 9:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:20 am - 7:10 am
BOS
-
MDW
2h 50mnonstop
$142Southwest
Wed, Feb 18 - Wed, Mar 4
Delta Logo
12:45 pm - 12:18 am
MDW
-
PWM
10h 33m
2 stops
Delta Logo
2:35 pm - 10:31 pm
PWM
-
MDW
8h 56m
2 stops
$240Delta
Mon, Feb 2 - Tue, Feb 3
Delta Logo
1:26 pm - 11:22 pm
MDW
-
PWM
8h 56m
2 stops
Delta Logo
12:10 pm - 5:55 pm
PWM
-
MDW
6h 45m
1 stop
$274Delta
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 $384 on average.

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 Tuesday and more expensive on a Thursday. On your return trip to Chicago Midway Airport, you should consider flying back on a Thursday, and avoid Sundays for better deals.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$66
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 8% 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 afternoon, when round-trip flights cost $387 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 $411.

Top tips for finding cheap flights to Maine

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Boston $78 one-way - $197 round-trip

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 4267 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
7.0Food
8.6Crew
Airline reviews

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

6.0 Goodha, Jan 2026
LAS - HOU
Read more Southwest reviews

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)