$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 9/15. 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

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
Portland1 stop$251
Bangor
Bangor2 stops$259
Boston
Bostonnonstop$137
Portland
Portland1 stop$251
Bangor
Bangor2 stops$259
Boston
Bostonnonstop$137

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

Fri, Oct 3 - Mon, Oct 6
Southwest Logo
9:20 pm - 12:40 amMDW-BOS
2h 20mnonstop
Southwest Logo
9:35 pm - 11:15 pmBOS-MDW
2h 40mnonstop
$137Southwest
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Sat, Dec 13 - Wed, Dec 17
Southwest Logo
12:50 pm - 4:05 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:35 pm - 9:05 pmBOS-MDW
4h 30m1 stop
$143Southwest
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Fri, Sep 26 - Sat, Oct 4
Frontier Logo
6:21 am - 8:11 amMDW-BOS
24h 50m1 stop
Frontier Logo
8:56 am - 12:44 pmBOS-MDW
28h 48m1 stop
$144Frontier
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Sat, Oct 25 - Wed, Oct 29
Southwest Logo
6:30 am - 2:30 pmMDW-BOS
7h 00m1 stop
Southwest Logo
5:15 am - 6:55 amBOS-MDW
2h 40mnonstop
$147Southwest
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Fri, Sep 26 - Sat, Oct 4
Frontier Logo
6:21 am - 8:11 amMDW-BOS
24h 50m1 stop
Frontier Logo
8:56 am - 12:44 pmBOS-MDW
28h 48m1 stop
$150Frontier
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Fri, Nov 7 - Sun, Nov 9
Frontier Logo
3:32 pm - 8:28 amMDW-BOS
15h 56m1 stop
Frontier Logo
10:04 am - 10:03 pmBOS-MDW
12h 59m1 stop
$151Frontier
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Mon, Sep 8 - Thu, Sep 11
Logo
8:19 am - 1:48 pmMDW-BOS
28h 29m1 stop
Logo
2:53 pm - 8:53 amBOS-MDW
19h 00m1 stop
$211
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Mon, Sep 15 - Tue, Sep 23
Logo
7:50 pm - 9:43 amMDW-BOS
12h 53m1 stop
Logo
6:10 am - 3:58 pmBOS-MDW
10h 48m2 stops
$233
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Wed, Oct 22 - Sat, Oct 25
Delta Logo
6:00 am - 12:22 pmMDW-PWM
5h 22m1 stop
Delta Logo
11:41 am - 5:43 pmPWM-MDW
7h 02m1 stop
$251Delta
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Wed, Oct 22 - Sat, Oct 25
Delta Logo
6:00 am - 12:22 pmMDW-PWM
5h 22m1 stop
Delta Logo
12:00 pm - 10:14 pmPWM-MDW
11h 14m2 stops
$256Delta
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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 $360 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 $360.

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 $368 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 Saturdays for better deals.

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Good to know

Low seasonJanuary
Cheapest flight$69
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 18% 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 $371 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 $68 one-way - $99 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 4241 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

2.0 MediocreMike, Aug 2025AUS - BWI
Read more Southwest reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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