$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 2/14. 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$229
Bangor
Bangor2 stops$285
Boston
Bostonnonstop$135
Portland
Portland1 stop$229
Bangor
Bangor2 stops$285
Boston
Bostonnonstop$135

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, Feb 17 - Mon, Feb 23
Southwest Logo
9:40 am - 12:55 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:20 am - 7:10 am
BOS
-
MDW
2h 50mnonstop
$135Southwest
Wed, Mar 4 - Wed, Mar 11
Southwest Logo
2:00 pm - 5:10 pm
MDW
-
BOS
2h 10mnonstop
Southwest Logo
6:00 pm - 7:50 pm
BOS
-
MDW
2h 50mnonstop
$137Southwest
Fri, Apr 3 - Sun, Apr 5
Southwest Logo
7:00 pm - 10:15 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
7:05 am - 9:00 am
BOS
-
MDW
2h 55mnonstop
$142Southwest
Wed, Feb 18 - Fri, Feb 20
Southwest Logo
5:35 pm - 8:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
7:05 pm - 8:55 pm
BOS
-
MDW
2h 50mnonstop
$146Southwest
Thu, Feb 26 - Sun, Mar 1
Southwest Logo
7:40 pm - 10:55 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
6:30 am - 10:35 am
BOS
-
MDW
5h 05m
1 stop
$147Southwest
Wed, Mar 4 - Wed, Mar 11
Multiple Airlines Logo
7:15 am - 11:44 pm
MDW
-
BOS
15h 29m
2 stops
Multiple Airlines Logo
3:54 pm - 1:41 pm
BOS
-
MDW
22h 47m
1 stop
$149Multiple Airlines
Wed, Feb 25 - Fri, Feb 27
Southwest Logo
5:35 pm - 8:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
12:50 pm - 7:50 pm
BOS
-
MDW
8h 00m
2 stops
$152Southwest
Wed, Apr 29 - Wed, May 13
Delta Logo
9:27 am - 3:57 pm
MDW
-
PWM
5h 30m
1 stop
Delta Logo
12:52 pm - 6:14 pm
PWM
-
MDW
6h 22m
1 stop
$229Delta
Wed, Apr 29 - Wed, May 13
Delta Logo
12:53 pm - 11:24 pm
MDW
-
PWM
9h 31m
2 stops
Delta Logo
12:52 pm - 6:14 pm
PWM
-
MDW
6h 22m
1 stop
$234Delta
Mon, Mar 2 - Mon, Mar 9
Delta Logo
9:50 am - 11:20 pm
MDW
-
PWM
12h 30m
2 stops
Delta Logo
2:30 pm - 10:31 pm
PWM
-
MDW
9h 01m
2 stops
$259Delta
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.

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 $384 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 Sundays for better deals.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$68
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly with an average 7% 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 $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 $411.

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 4274 reviews
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

10.0 ExcellentMeghan, Feb 2026
MCO - DEN
Read more Southwest reviews

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)