$157 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 10/26. 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.
Flight Deals
Cheap Flights from Midway to Maine
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysBook 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, Oct 24 - Wed, Oct 28
4:10 pm - 7:25 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$353Southwest
Mon, Oct 26 - Tue, Oct 27
6:40 pm - 9:55 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$353Southwest
Wed, Oct 28 - Wed, Oct 28
7:45 am - 10:55 amMDW Chicago Midway-PWM Portland
2h 10mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$353Southwest
Mon, Oct 26 - Wed, Oct 28
6:40 pm - 9:55 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$353Southwest
Tue, Oct 27 - Wed, Nov 4
7:45 am - 10:55 amMDW Chicago Midway-PWM Portland
2h 10mnonstop
12:45 pm - 6:55 pmPWM Portland-MDW Chicago Midway
7h 10m1 stop Baltimore/Washington
$363Southwest
Sat, Oct 24 - Tue, Oct 27
4:10 pm - 7:25 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
11:35 am - 4:55 pmPWM Portland-MDW Chicago Midway
6h 20m1 stop Nashville Intl
$363Southwest
Mon, Oct 26 - Tue, Oct 27
6:40 pm - 9:55 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
5:40 am - 11:20 amPWM Portland-MDW Chicago Midway
6h 40m1 stop Baltimore/Washington
$363Southwest
Sat, Oct 24 - Wed, Oct 28
6:45 am - 2:50 pmMDW Chicago Midway-PWM Portland
7h 05m1 stop Nashville Intl
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$363Southwest
Mon, Oct 26 - Wed, Oct 28
6:25 pm - 11:55 pmMDW Chicago Midway-PWM Portland
4h 30m1 stop Baltimore/Washington
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$363Southwest
Wed, Oct 21 - Sat, Oct 31
7:45 am - 10:55 amMDW Chicago Midway-PWM Portland
2h 10mnonstop
7:20 am - 1:20 pmPWM Portland-MDW Chicago Midway
7h 00m1 stop Baltimore/Washington
$363Southwest
Recent one-way flight deals from Midway to Maine
Mon, Oct 26
6:15 am - 4:24 pmMDW Chicago Midway-PWM Portland
33h 09m2 stops Atlanta Hartsfield-Jackson Raleigh-Durham
$157Multiple Airlines
Tue, Oct 27
9:53 am - 4:24 pmMDW Chicago Midway-PWM Portland
29h 31m2 stops Atlanta Hartsfield-Jackson Raleigh-Durham
$163Multiple Airlines
Mon, Nov 16
6:16 am - 9:08 amMDW Chicago Midway-PWM Portland
49h 52m2 stops Atlanta Hartsfield-Jackson Orlando
$167Multiple Airlines
Sun, Nov 1
6:16 am - 1:57 pmMDW Chicago Midway-PWM Portland
30h 41m2 stops Atlanta Hartsfield-Jackson Columbus
$168Multiple Airlines
Mon, Nov 2
6:16 am - 9:08 amMDW Chicago Midway-PWM Portland
49h 52m2 stops Atlanta Hartsfield-Jackson Orlando
$168Multiple Airlines
Tue, Nov 17
6:08 am - 9:08 amMDW Chicago Midway-PWM Portland
26h 00m2 stops Atlanta Hartsfield-Jackson Orlando
$168Multiple Airlines
Sun, Nov 1
6:16 am - 1:57 pmMDW Chicago Midway-PWM Portland
30h 41m2 stops Atlanta Hartsfield-Jackson Columbus
$169Multiple Airlines
Tue, Oct 27
9:53 am - 4:24 pmMDW Chicago Midway-PWM Portland
29h 31m2 stops Atlanta Hartsfield-Jackson Raleigh-Durham
$172Multiple Airlines
Mon, Oct 19
6:15 am - 4:24 pmMDW Chicago Midway-PWM Portland
33h 09m2 stops Atlanta Hartsfield-Jackson Raleigh-Durham
$176Multiple Airlines
Mon, Oct 26
6:40 pm - 9:55 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
$177Southwest
Recent last minute flight deals from Midway to Maine
Sat, Oct 3 - Wed, Oct 7
4:50 pm - 10:10 pmMDW Chicago Midway-PWM Portland
4h 20m1 stop Baltimore/Washington
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$427Southwest
Sat, Oct 3 - Wed, Oct 7
11:55 am - 10:10 pmMDW Chicago Midway-PWM Portland
9h 15m2 stops Tampa Baltimore/Washington
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$432Southwest
Sat, Oct 3 - Wed, Oct 7
1:19 pm - 11:56 pmMDW Chicago Midway-PWM Portland
9h 37m2 stops Detroit Metropolitan Wayne County New York John F Kennedy Intl
11:55 am - 4:47 pmPWM Portland-MDW Chicago Midway
5h 52m1 stop Minneapolis St Paul
$442Delta
Sat, Oct 3 - Wed, Oct 7
11:55 am - 10:10 pmMDW Chicago Midway-PWM Portland
9h 15m2 stops Tampa Baltimore/Washington
5:40 am - 2:40 pmPWM Portland-MDW Chicago Midway
10h 00m2 stops Baltimore/Washington Orlando
$462Southwest
Sat, Oct 3 - Wed, Oct 7
4:10 pm - 7:20 pmMDW Chicago Midway-PWM Portland
2h 10mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$467Southwest
Sun, Oct 4 - Tue, Oct 6
7:50 pm - 11:05 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$467Southwest
Tue, Oct 6 - Sat, Oct 10
7:45 am - 10:55 amMDW Chicago Midway-PWM Portland
2h 10mnonstop
4:35 pm - 6:10 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$467Southwest
Sun, Oct 4 - Wed, Oct 7
7:50 pm - 11:05 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$467Southwest
Mon, Oct 5 - Tue, Oct 6
6:40 pm - 9:55 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$467Southwest
Sat, Oct 3 - Mon, Oct 5
4:10 pm - 7:20 pmMDW Chicago Midway-PWM Portland
2h 10mnonstop
5:20 am - 10:00 amPWM Portland-MDW Chicago Midway
5h 40m1 stop Baltimore/Washington
$477Southwest
Recent direct flight deals from Midway to Maine
Sat, Oct 24 - Wed, Oct 28
4:10 pm - 7:25 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$353Southwest
Mon, Oct 26 - Wed, Oct 28
6:40 pm - 9:55 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$353Southwest
Wed, Oct 28 - Wed, Oct 28
7:45 am - 10:55 amMDW Chicago Midway-PWM Portland
2h 10mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$353Southwest
Mon, Oct 26 - Tue, Oct 27
6:40 pm - 9:55 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$353Southwest
Sat, Oct 24 - Tue, Oct 27
4:10 pm - 7:25 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$371Southwest
Mon, Oct 26 - Fri, Oct 30
6:40 pm - 9:55 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
6:30 am - 8:05 amPWM Portland-MDW Chicago Midway
2h 35mnonstop
$371Southwest
Tue, Oct 20 - Tue, Oct 27
7:45 am - 10:55 amMDW Chicago Midway-PWM Portland
2h 10mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$385Southwest
Fri, Oct 23 - Tue, Oct 27
6:40 pm - 9:55 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$389Southwest
Sun, Oct 25 - Wed, Oct 28
7:50 pm - 11:05 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$435Southwest
Sat, Oct 17 - Wed, Oct 21
4:10 pm - 7:25 pmMDW Chicago Midway-PWM Portland
2h 15mnonstop
6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway
2h 35mnonstop
$449Southwest
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.
Prices
Airlines
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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 $381 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 $381.
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 100% cheaper than evening flights, on average. The most expensive time of day to fly to Maine is generally in the evening, which is peak travel time and where the average cost of a ticket is $348.
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 $442 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 Friday and more expensive on a Saturday. On your return trip to Chicago Midway Airport, you should consider flying back on a Friday, and avoid Sundays for better deals.
How long does a flight from Chicago Midway Airport to Maine take?
The duration of a flight to Maine depends on your arrival airport. The shortest routes to Maine from Chicago Midway Airport are to Portland, which takes 2h 10m, and Bangor, which takes 8h 26m.
Which cabin class options are there for flights between Chicago Midway Airport and Maine?
The average price of round-trip flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.
What’s the earliest departure time from Chicago Midway Airport to Maine?
The earliest flight from Chicago Midway Airport to Maine departs at 7:45 am, landing in Portland at 10:55 am.
What’s the latest departure time from Chicago Midway Airport to Maine?
If you prefer to fly at night, the latest flight from Chicago Midway Airport to Maine jets off at 7:50 pm and lands in Portland at 11:05 pm.
Good to know
Low season | January |
|---|---|
High season | October |
Cheapest flight | $157 |
FAQs - booking Maine flights
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Information on your arrival and departure airports
Cabin class types available on flights to Midway
Cabin classes available on flights to Maine. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from domestic origins to Midway
Flights from all regions of Midway to Maine. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.