MDW

$64 Find Cheap Flights from Maine to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 1/18. 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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Everything you should know

Cheapest round-trip
$128
Overall average: $217
Frontier
Wed 1/28Tue 2/3
BOS - MDW • 1 stop
Cheapest non-stop
$132
Typical prices: $158-$347
Southwest
Thu 1/1Thu 1/8
BOS - MDW • Non-stop
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We hope you love your trip to Midway!
Flight Deals
Useful Info
Flight Deals

Cheap Flights from Maine to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Maine to Midway 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 Maine to Midway

Wed, Jan 28 - Tue, Feb 3
Frontier Logo
6:00 am - 12:05 pm
BOS
-
MDW
7h 05m1 stop
Frontier Logo
1:20 pm - 1:03 am
MDW
-
BOS
10h 43m1 stop
$128Frontier
Thu, Jan 1 - Thu, Jan 8
Southwest Logo
5:30 am - 7:15 am
BOS
-
MDW
2h 45mnonstop
Southwest Logo
2:00 pm - 5:10 pm
MDW
-
BOS
2h 10mnonstop
$132Southwest
Mon, Feb 9 - Tue, Feb 10
Southwest Logo
5:20 am - 7:10 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
5:35 pm - 8:50 pm
MDW
-
BOS
2h 15mnonstop
$137Southwest
Thu, Jan 15 - Mon, Jan 19
Multiple Airlines Logo
3:43 pm - 9:09 am
BOS
-
MDW
18h 26m1 stop
Multiple Airlines Logo
7:20 pm - 4:19 pm
MDW
-
BOS
19h 59m1 stop
$138Multiple Airlines
Wed, Jan 7 - Sat, Jan 10
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
10:15 am - 1:30 pm
MDW
-
BOS
2h 15mnonstop
$142Southwest
Wed, Jan 21 - Mon, Jan 26
Frontier Logo
6:00 am - 12:05 pm
BOS
-
MDW
7h 05m1 stop
Frontier Logo
5:01 pm - 1:13 am
MDW
-
BOS
7h 12m1 stop
$145Frontier
Wed, Jan 28 - Thu, Jan 29
Frontier Logo
6:00 am - 12:05 pm
BOS
-
MDW
7h 05m1 stop
Frontier Logo
5:01 pm - 1:13 am
MDW
-
BOS
7h 12m1 stop
$146Frontier
Sat, Jan 10 - Sat, Jan 10
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
10:15 am - 1:30 pm
MDW
-
BOS
2h 15mnonstop
$147Southwest
Tue, May 5 - Tue, May 12
Delta Logo
12:50 pm - 6:31 pm
PWM
-
MDW
6h 41m1 stop
Delta Logo
9:30 am - 4:15 pm
MDW
-
PWM
5h 45m1 stop
$279Delta
Sat, Jan 17 - Mon, Jan 19
Delta Logo
12:50 pm - 10:07 pm
PWM
-
MDW
10h 17m2 stops
Delta Logo
1:26 pm - 11:22 pm
MDW
-
PWM
8h 56m2 stops
$289Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$64
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Boston to Chicago Midway Airport

FAQs for booking Maine to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Maine to Chicago Midway Airport?

    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 Maine to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Maine to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from 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 Maine to Chicago Midway Airport?

    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 to Chicago Midway Airport with an airline and back to Maine with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Maine to Chicago Midway Airport?

    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 to Chicago Midway Airport from Maine up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)