$93 Find Cheap Flights from Chicago Midway Airport to Maine - Compare and Save

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 9/8. 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

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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
Portland2 stops$301
Bangor
Bangor1 stop$281
Boston
Boston1 stop$170
Portland
Portland2 stops$301
Bangor
Bangor1 stop$281
Boston
Boston1 stop$170

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

Fri, Sep 11 - Mon, Sep 14
Southwest Logo
9:20 am - 5:05 pm
MDW
-
BOS
6h 45m
1 stop
Southwest Logo
8:20 pm - 10:00 pm
BOS
-
MDW
2h 40mnonstop
$170Southwest
Wed, Aug 12 - Sat, Aug 22
Southwest Logo
6:40 am - 9:55 am
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:30 am - 9:30 am
BOS
-
MDW
5h 00m
1 stop
$172Southwest
Wed, Aug 19 - Wed, Aug 19
Southwest Logo
8:15 am - 2:00 pm
MDW
-
BOS
4h 45m
1 stop
Southwest Logo
4:55 pm - 8:45 pm
BOS
-
MDW
4h 50m
1 stop
$173Southwest
Sat, Aug 1 - Mon, Aug 3
Southwest Logo
5:25 am - 8:40 am
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:25 am - 7:00 am
BOS
-
MDW
2h 35mnonstop
$175Southwest
Sat, Aug 1 - Wed, Aug 12
Southwest Logo
5:45 pm - 9:10 pm
MDW
-
BOS
2h 25mnonstop
Southwest Logo
5:35 am - 11:50 am
BOS
-
MDW
7h 15m
1 stop
$176Southwest
Sat, Aug 22 - Mon, Aug 24
Southwest Logo
9:05 am - 12:25 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
6:40 pm - 8:20 pm
BOS
-
MDW
2h 40mnonstop
$178Southwest
Sun, Aug 9 - Sat, Aug 22
Southwest Logo
7:55 am - 11:25 am
MDW
-
BOS
2h 30mnonstop
Southwest Logo
8:40 am - 10:15 am
BOS
-
MDW
2h 35mnonstop
$179Southwest
Tue, Aug 18 - Tue, Aug 25
Southwest Logo
6:30 am - 2:40 pm
MDW
-
BOS
7h 10m
1 stop
Southwest Logo
7:15 pm - 8:50 pm
BOS
-
MDW
2h 35mnonstop
$180Southwest
Sat, Oct 17 - Sat, Oct 24
Delta Logo
6:00 am - 1:34 pm
MDW
-
BGR
6h 34m
1 stop
Delta Logo
2:40 pm - 10:25 pm
BGR
-
MDW
8h 45m
1 stop
$281Delta
Tue, Aug 25 - Tue, Sep 1
Delta Logo
12:46 pm - 11:40 pm
MDW
-
BGR
9h 54m
2 stops
Delta Logo
5:20 am - 3:44 pm
BGR
-
MDW
11h 24m
2 stops
$291Delta
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 5 days was to Portland, at $390 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 5 days was $390.

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 $348 on average. Morning departures are around 18% 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 $410.

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 $390, 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 Saturday and more expensive on a Sunday. On your return trip to Chicago Midway Airport, you should consider flying back on a Friday, 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 36% increase in price.
Most popular time to fly with an average 10% 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.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)