$68 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 5/30. 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
Portland1 stop$209
Bangor
Bangor1 stop$285
Boston
Boston1 stop$125
Portland
Portland1 stop$209
Bangor
Bangor1 stop$285
Boston
Boston1 stop$125

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, Apr 4 - Sat, Apr 11
Southwest Logo
6:25 am - 1:45 pm
MDW
-
BOS
6h 20m
1 stop
Southwest Logo
1:50 pm - 3:30 pm
BOS
-
MDW
2h 40mnonstop
$125Southwest
Sat, Apr 11 - Mon, Apr 13
Southwest Logo
11:25 am - 2:45 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
3:45 pm - 5:30 pm
BOS
-
MDW
2h 45mnonstop
$126Southwest
Sat, Apr 4 - Sat, Apr 11
Southwest Logo
6:45 pm - 10:00 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
1:50 pm - 3:30 pm
BOS
-
MDW
2h 40mnonstop
$136Southwest
Sat, Apr 11 - Tue, Apr 14
Southwest Logo
7:45 am - 11:00 am
MDW
-
BOS
2h 15mnonstop
Southwest Logo
10:45 am - 12:25 pm
BOS
-
MDW
2h 40mnonstop
$137Southwest
Wed, Mar 25 - Sat, Mar 28
Southwest Logo
12:10 pm - 3:20 pm
MDW
-
BOS
2h 10mnonstop
Southwest Logo
6:30 am - 8:20 am
BOS
-
MDW
2h 50mnonstop
$140Southwest
Sat, May 9 - Wed, May 13
Southwest Logo
4:20 pm - 11:40 pm
MDW
-
BOS
6h 20m
2 stops
Southwest Logo
7:20 am - 9:05 am
BOS
-
MDW
2h 45mnonstop
$141Southwest
Sun, Aug 30 - Sat, Sep 5
Delta Logo
6:00 am - 1:35 pm
MDW
-
BGR
6h 35m
1 stop
Delta Logo
2:40 pm - 9:46 pm
BGR
-
MDW
8h 06m
1 stop
$285Delta
Fri, Apr 17 - Sat, Apr 25
Delta Logo
1:24 pm - 11:31 pm
MDW
-
BGR
9h 07m
2 stops
Delta Logo
6:00 am - 12:43 pm
BGR
-
MDW
7h 43m
2 stops
$340Delta
Sat, Aug 29 - Sat, Sep 5
Delta Logo
6:00 am - 1:35 pm
MDW
-
BGR
6h 35m
1 stop
Delta Logo
2:40 pm - 9:46 pm
BGR
-
MDW
8h 06m
1 stop
$350Delta
Thu, Mar 26 - Mon, Mar 30
Multiple Airlines Logo
9:10 am - 7:13 pm
MDW
-
BGR
9h 03m
1 stop
Multiple Airlines Logo
6:54 pm - 8:54 pm
BGR
-
MDW
27h 00m
2 stops
$369Multiple Airlines
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 $434 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 $434.

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 $410 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 Mondays for better deals.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$68
Best time to beat the crowds but there is an average 43% increase in price.
Most popular time to fly with an average 4% 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.

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 4319 reviews
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)