$94 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 5/29. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Maine

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portlandnonstop$302
Bangor
Bangor2 stops$286
Boston
Bostonnonstop$176
Portland
Portlandnonstop$302
Bangor
Bangor2 stops$286
Boston
Bostonnonstop$176

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, Jun 6 - Tue, Jun 9
Southwest Logo
5:25 am - 8:40 am
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:30 pm - 7:20 pm
BOS
-
MDW
2h 50mnonstop
$176Southwest
Sat, Jun 6 - Mon, Jun 8
Southwest Logo
5:45 pm - 9:05 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
4:45 pm - 6:35 pm
BOS
-
MDW
2h 50mnonstop
$181Southwest
Tue, Jun 9 - Wed, Jun 10
Southwest Logo
9:00 am - 12:15 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
7:30 am - 9:10 am
BOS
-
MDW
2h 40mnonstop
$187Southwest
Wed, Jul 29 - Wed, Aug 5
Frontier Logo
12:11 pm - 1:23 am
MDW
-
BOS
12h 12m
1 stop
Frontier Logo
6:00 am - 11:07 am
BOS
-
MDW
6h 07m
1 stop
$190Frontier
Sun, Jun 7 - Wed, Jun 10
Southwest Logo
5:15 am - 8:25 am
MDW
-
BOS
2h 10mnonstop
Southwest Logo
3:45 pm - 5:30 pm
BOS
-
MDW
2h 45mnonstop
$192Southwest
Wed, Jun 10 - Thu, Jun 11
Southwest Logo
2:40 pm - 6:00 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
5:25 am - 7:00 am
BOS
-
MDW
2h 35mnonstop
$196Southwest
Mon, Aug 17 - Wed, Aug 26
Frontier Logo
12:11 pm - 1:23 am
MDW
-
BOS
12h 12m
1 stop
Frontier Logo
6:00 am - 11:09 am
BOS
-
MDW
6h 09m
1 stop
$204Frontier
Wed, Sep 2 - Sat, Sep 5
Delta Logo
1:05 pm - 11:28 pm
MDW
-
BGR
9h 23m
2 stops
Delta Logo
2:40 pm - 9:46 pm
BGR
-
MDW
8h 06m
1 stop
$286Delta
Tue, Aug 25 - Tue, Sep 1
Delta Logo
12:46 pm - 11:40 pm
MDW
-
BGR
9h 54m
2 stops
Delta Logo
6:00 am - 12:30 pm
BGR
-
MDW
7h 30m
2 stops
$291Delta
Mon, Sep 7 - Sat, Sep 12
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
$295Delta
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 7 days was to Portland, at $289 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 7 days was $289.

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 31% more expensive than evening flights, 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.

No, with an average price for the route of $386, 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 Tuesday, and avoid Sundays for better deals.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$93
Best time to beat the crowds but there is an average 43% 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.

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 $108 one-way - $216 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.
7.9
SouthwestOverall score based on 4277 reviews
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
7.5Entertainment
Airline reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

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.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)