$74 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 4/29. 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$269
Bangor
Bangor2 stops$291
Boston
Boston1 stop$140
Portland
Portlandnonstop$269
Bangor
Bangor2 stops$291
Boston
Boston1 stop$140

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, Apr 29 - Wed, May 6
Frontier Logo
2:15 pm - 1:31 am
MDW
-
BOS
10h 16m
1 stop
Frontier Logo
12:01 pm - 10:02 pm
BOS
-
MDW
11h 01m
1 stop
$140Frontier
Tue, May 12 - Tue, May 12
Southwest Logo
12:45 pm - 4:05 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
6:00 pm - 10:15 pm
BOS
-
MDW
5h 15m
1 stop
$149Southwest
Wed, May 6 - Wed, May 13
Frontier Logo
12:04 pm - 1:24 am
MDW
-
BOS
12h 20m
1 stop
Frontier Logo
12:01 pm - 10:02 pm
BOS
-
MDW
11h 01m
1 stop
$151Frontier
Tue, May 5 - Sat, May 9
Southwest Logo
6:00 pm - 9:20 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
3:30 pm - 5:15 pm
BOS
-
MDW
2h 45mnonstop
$153Southwest
Tue, May 12 - Tue, May 19
Southwest Logo
2:35 pm - 10:40 pm
MDW
-
BOS
7h 05m
2 stops
Southwest Logo
10:45 am - 12:25 pm
BOS
-
MDW
2h 40mnonstop
$154Southwest
Tue, Apr 21 - Tue, Apr 28
Frontier Logo
2:15 pm - 1:31 am
MDW
-
BOS
10h 16m
1 stop
Frontier Logo
12:52 pm - 7:31 pm
BOS
-
MDW
7h 39m
1 stop
$156Frontier
Wed, Apr 29 - Sun, May 3
Southwest Logo
12:45 pm - 4:05 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
10:35 am - 12:15 pm
BOS
-
MDW
2h 40mnonstop
$158Southwest
Wed, May 6 - Wed, May 6
Southwest Logo
5:30 am - 1:40 pm
MDW
-
BOS
7h 10m
1 stop
Southwest Logo
5:55 pm - 9:50 pm
BOS
-
MDW
4h 55m
1 stop
$159Southwest
Wed, May 27 - Sat, May 30
Delta Logo
1:22 pm - 11:33 pm
MDW
-
BGR
9h 11m
2 stops
Delta Logo
6:00 am - 5:56 pm
BGR
-
MDW
12h 56m
2 stops
$291Delta
Tue, Jun 9 - Tue, Jun 16
Delta Logo
12:45 pm - 11:29 pm
MDW
-
PWM
9h 44m
2 stops
Delta Logo
6:00 am - 6:18 pm
PWM
-
MDW
13h 18m
2 stops
$300Delta
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 $259 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 $259.

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 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 $403.

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 $397 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 Wednesday and more expensive on a Thursday. On your return trip to Chicago Midway Airport, you should consider flying back on a Tuesday, and avoid Sundays for better deals.

Good to know

Low seasonJanuary
Cheapest flight$76
Best time to beat the crowds but there is an average 40% increase in price.
Most popular time to fly with an average 1% 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.

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 $102 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 4334 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

It was as expected and I was grateful for the wheel chair help and ease of use.

10.0 ExcellentAnonymous, Apr 2026
LAS - PDX
Read more Southwest reviews

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

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

Information on your arrival and departure airports