$59 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 12/24. 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$284
Bangor
Bangor2 stops$259
Boston
Bostonnonstop$122
Portland
Portland2 stops$284
Bangor
Bangor2 stops$259
Boston
Bostonnonstop$122

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, Dec 6 - Tue, Dec 9
Southwest Logo
5:35 pm - 8:50 pmMDW-BOS
2h 15mnonstop
Southwest Logo
1:35 pm - 3:20 pmBOS-MDW
2h 45mnonstop
$122Southwest
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Thu, Dec 11 - Sun, Dec 14
Frontier Logo
3:10 pm - 9:57 amMDW-BOS
17h 47m1 stop
Frontier Logo
11:28 am - 6:12 pmBOS-MDW
7h 44m1 stop
$124Frontier
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Thu, Dec 4 - Sun, Dec 7
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
Southwest Logo
5:15 am - 7:00 amBOS-MDW
2h 45mnonstop
$127Southwest
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Thu, Dec 11 - Mon, Dec 15
Frontier Logo
3:10 pm - 9:57 amMDW-BOS
17h 47m1 stop
Frontier Logo
11:23 am - 10:12 pmBOS-MDW
11h 49m1 stop
$128Frontier
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Fri, Feb 6 - Sun, Feb 8
Frontier Logo
5:01 pm - 1:13 amMDW-BOS
7h 12m1 stop
Frontier Logo
6:00 am - 11:45 amBOS-MDW
6h 45m1 stop
$129Frontier
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Wed, Dec 3 - Sun, Dec 7
Frontier Logo
2:49 pm - 10:22 amMDW-BOS
18h 33m1 stop
Frontier Logo
11:28 am - 10:12 pmBOS-MDW
11h 44m1 stop
$130Frontier
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Sat, Dec 20 - Tue, Dec 30
Southwest Logo
8:40 pm - 11:55 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:15 am - 7:00 amBOS-MDW
2h 45mnonstop
$131Southwest
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Mon, Dec 15 - Wed, Dec 17
Southwest Logo
1:30 pm - 4:45 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:35 pm - 9:05 pmBOS-MDW
4h 30m1 stop
$132Southwest
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Tue, Jan 13 - Sat, Jan 17
Delta Logo
11:21 am - 11:25 pmMDW-BGR
11h 04m2 stops
Delta Logo
1:09 pm - 10:07 pmBGR-MDW
9h 58m2 stops
$259Delta
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Tue, Mar 3 - Wed, Mar 4
Delta Logo
12:46 pm - 12:20 amMDW-PWM
10h 34m2 stops
Delta Logo
12:15 pm - 5:37 pmPWM-MDW
6h 22m1 stop
$284Delta
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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 $591 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 $591.

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 $591 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.

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Good to know

Low seasonJanuary
Cheapest flight$59
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 11% lower on average.
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 $372 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.

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 4248 reviews
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

10.0 ExcellentIlevba, Nov 2025DCA - DAL
Read more Southwest reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

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.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)