$79 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 9/2. 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$240
Bangor
Bangor2 stops$305
Boston
Bostonnonstop$148
Portland
Portlandnonstop$240
Bangor
Bangor2 stops$305
Boston
Bostonnonstop$148

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, May 19 - Tue, May 26
Southwest Logo
7:45 am - 11:00 am
MDW
-
BOS
2h 15mnonstop
Southwest Logo
7:20 am - 9:05 am
BOS
-
MDW
2h 45mnonstop
$148Southwest
Tue, May 19 - Tue, May 26
Southwest Logo
1:55 pm - 10:20 pm
MDW
-
BOS
7h 25m
1 stop
Southwest Logo
10:45 am - 12:25 pm
BOS
-
MDW
2h 40mnonstop
$149Southwest
Tue, May 12 - Tue, May 19
Southwest Logo
3:15 pm - 6:35 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
10:45 am - 12:25 pm
BOS
-
MDW
2h 40mnonstop
$151Southwest
Tue, Jun 9 - Thu, Jul 2
Southwest Logo
6:05 pm - 9:20 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:25 am - 7:00 am
BOS
-
MDW
2h 35mnonstop
$156Southwest
Tue, Jun 2 - Wed, Jun 10
Delta Logo
6:36 pm - 11:29 pm
MDW
-
BOS
3h 53m
1 stop
Delta Logo
5:30 am - 9:14 am
BOS
-
MDW
4h 44m
1 stop
$157Delta
Tue, May 12 - Wed, May 13
Southwest Logo
1:55 pm - 10:20 pm
MDW
-
BOS
7h 25m
1 stop
Southwest Logo
2:25 pm - 4:05 pm
BOS
-
MDW
2h 40mnonstop
$158Southwest
Sat, May 9 - Mon, May 11
Southwest Logo
11:25 am - 2:45 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
6:55 pm - 8:45 pm
BOS
-
MDW
2h 50mnonstop
$159Southwest
Thu, May 7 - Tue, May 12
Frontier Logo
12:19 pm - 1:24 am
MDW
-
BOS
12h 05m
1 stop
Frontier Logo
6:00 am - 11:09 am
BOS
-
MDW
6h 09m
1 stop
$160Frontier
Tue, Jun 9 - Mon, Jun 15
Delta Logo
9:17 am - 4:00 pm
MDW
-
PWM
5h 43m
1 stop
Delta Logo
11:48 am - 6:18 pm
PWM
-
MDW
7h 30m
1 stop
$243Delta
Tue, Jun 9 - Tue, Jun 16
Delta Logo
11:05 am - 11:29 pm
MDW
-
PWM
11h 24m
2 stops
Delta Logo
6:00 am - 12:00 pm
PWM
-
MDW
7h 00m
1 stop
$248Delta
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 $269 on average. Morning departures are around 41% 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 Thursday. On your return trip to Chicago Midway Airport, you should consider flying back on a Saturday, and avoid Sundays for better deals.

Good to know

Low seasonJanuary
Cheapest flight$79
Best time to beat the crowds but there is an average 40% increase in price.
Most popular time to fly with an average 2% 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 $110 one-way - $221 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 4327 reviews
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

10.0 ExcellentJasmine, Apr 2026
LGB - HNL
Read more Southwest reviews

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

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

Information on your arrival and departure airports