$84 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 6/6. 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
Portlandnonstop$307
Bangor
Bangor2 stops$291
Boston
Bostonnonstop$167
Portland
Portlandnonstop$307
Bangor
Bangor2 stops$291
Boston
Bostonnonstop$167

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

Tue, Jun 23 - Wed, Jun 24
Southwest Logo
6:05 pm - 9:20 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
$167Southwest
Mon, Jun 1 - Tue, Jun 2
Southwest Logo
9:25 am - 12:40 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
7:20 am - 9:05 am
BOS
-
MDW
2h 45mnonstop
$172Southwest
Fri, Jun 5 - Mon, Jun 8
Southwest Logo
4:00 pm - 7:20 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
6:45 pm - 8:35 pm
BOS
-
MDW
2h 50mnonstop
$177Southwest
Thu, May 28 - Mon, Jun 1
Frontier Logo
12:27 pm - 1:24 am
MDW
-
BOS
11h 57m
1 stop
Frontier Logo
6:00 am - 11:09 am
BOS
-
MDW
6h 09m
1 stop
$180Frontier
Tue, Jul 14 - Thu, Jul 16
Southwest Logo
5:30 pm - 11:20 pm
MDW
-
BOS
4h 50m
1 stop
Southwest Logo
1:10 pm - 2:45 pm
BOS
-
MDW
2h 35mnonstop
$182Southwest
Tue, Jun 9 - Tue, Jun 16
Frontier Logo
12:27 pm - 7:52 am
MDW
-
BOS
18h 25m
1 stop
Frontier Logo
6:00 am - 10:11 pm
BOS
-
MDW
17h 11m
1 stop
$189Frontier
Wed, Aug 19 - Tue, Aug 25
Frontier Logo
12:04 pm - 1:27 am
MDW
-
BOS
12h 23m
1 stop
Frontier Logo
6:00 am - 11:12 am
BOS
-
MDW
6h 12m
1 stop
$190Frontier
Tue, Jun 9 - Tue, Jun 16
Delta Logo
11:05 am - 11:35 pm
MDW
-
BGR
11h 30m
2 stops
Delta Logo
5:05 am - 4:16 pm
BGR
-
MDW
12h 11m
2 stops
$291Delta
Sat, Jun 27 - Mon, Jun 29
Delta Logo
9:54 am - 9:35 pm
MDW
-
BGR
10h 41m
2 stops
Delta Logo
2:45 pm - 10:17 pm
BGR
-
MDW
8h 32m
1 stop
$314Delta
Tue, Jul 21 - Sat, Jul 25
Delta Logo
11:05 am - 11:11 pm
MDW
-
BGR
11h 06m
2 stops
Delta Logo
6:00 am - 3:37 pm
BGR
-
MDW
10h 37m
2 stops
$323Delta
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 $269 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 $269.

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

The average price for all round-trip flights from Chicago Midway Airport 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 evening, when round-trip flights cost $308 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 afternoon, which is peak travel time and where the average cost of a ticket is $387.

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.

No, with an average price for the route of $348, prices are generally cheapest when you fly direct.

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

Find deals

Good to know

Low seasonJanuary
Cheapest flight$84
Best time to beat the crowds but there is an average 42% increase in price.
Most popular time to fly and prices are also 20% 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.

  • How many flights are there between Chicago Midway Airport and Maine per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago Midway Airport and lands in Maine, with an average flight time of 2h 15m. The most common departure time is 6:00 pm and most flights take off in the evening. Each week, there are 7 flights.

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 4298 reviews
7.0Food
7.5Entertainment
8.6Crew
8.1Boarding
8.0Comfort
Airline reviews

I'm glad it wasn't only 75% full because I could get a good seat

8.0 ExcellentBobby, May 2026
BNA - GSP
Read more Southwest reviews

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)