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Cheap flights from Chicago Midway Airport to Maine from $52

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Maine departing on 1/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Maine

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to Maine that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to Maine.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to Maine? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Maine, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to Maine

Find recent round-trip train or bus tickets from Chicago Midway Airport to Maine.

All round-trip flight deals to Maine

The cheapest plane tickets to Maine found on KAYAK recently.
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
5:45 am - 1:24 pmBOS-MDW
8h 39m1 stop
$103Frontier
Find Deal
Wed, Dec 11 - Wed, Dec 18
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
$104Frontier
Find Deal
Tue, Dec 10 - Wed, Dec 11
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
6:40 am - 8:25 amBOS-MDW
2h 45mnonstop
$158Southwest
Find Deal
Fri, Dec 13 - Sun, Dec 15
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
8:15 pm - 10:00 pmBOS-MDW
2h 45mnonstop
$179Southwest
Find Deal
Fri, Dec 13 - Sat, Jan 4
5:50 pm - 10:39 pmMDW-PWM
3h 49m1 stop
5:05 am - 8:58 amPWM-MDW
4h 53m1 stop
$228Delta
Find Deal
Sat, Dec 14 - Tue, Dec 17
4:58 pm - 12:08 amMDW-PWM
6h 10m1 stop
6:05 am - 5:01 pmPWM-MDW
11h 56m2 stops
$233Delta
Find Deal
Sat, Dec 14 - Tue, Dec 17
11:48 am - 12:17 pmMDW-PWM
23h 29m3 stops
4:46 pm - 5:47 pmPWM-MDW
26h 01m3 stops
$1,201WestJet
Find Deal
Tue, Dec 31 - Mon, Jan 6
11:48 am - 4:35 pmMDW-PWM
27h 47m3 stops
4:46 pm - 5:47 pmPWM-MDW
26h 01m3 stops
$1,237
Find Deal
Wed, Jan 1 - Mon, Jan 6
4:50 pm - 4:35 pmMDW-PWM
22h 45m3 stops
4:46 pm - 5:47 pmPWM-MDW
26h 01m3 stops
$1,292
Find Deal
Wed, Jan 1 - Mon, Jan 6
9:38 am - 11:49 amMDW-PWM
25h 11m3 stops
4:30 pm - 1:31 pmPWM-MDW
22h 01m3 stops
$1,399WestJet
Find Deal
Thu, Dec 12 - Sun, Dec 15
5:24 pm - 12:30 amMDW-BOS
6h 06m1 stop
$52Frontier
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Tue, Jan 14
5:24 pm - 12:30 amMDW-BOS
6h 06m1 stop
$53Frontier
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Tue, Jan 7
10:05 am - 1:20 pmMDW-BOS
2h 15mnonstop
$79Southwest
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Mon, Feb 3
5:40 am - 8:55 amMDW-BOS
2h 15mnonstop
$95Southwest
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Thu, Nov 28
5:50 pm - 10:39 pmMDW-PWM
3h 49m1 stop
$114Delta
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Sat, Dec 14
1:30 pm - 12:10 amMDW-PWM
9h 40m2 stops
$119Delta
Find Deal
Wed, Dec 18
9:21 am - 9:07 pmMDW-BOS
34h 46m3 stops
Tue, Jan 7
9:21 am - 4:54 pmMDW-BOS
30h 33m3 stops
Thu, Jan 30
10:19 am - 4:44 pmMDW-PWM
29h 25m3 stops
$372WestJet
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Wed, Feb 12
10:19 am - 4:43 pmMDW-PWM
29h 24m3 stops
$373WestJet
Find Deal
Mon, Jan 13
6:48 pm - 12:31 amMDW-BOS
4h 43m1 stop
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
$208Frontier
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Tue, Nov 26 - Tue, Dec 10
6:48 pm - 12:31 amMDW-BOS
4h 43m1 stop
12:38 pm - 9:02 pmBOS-MDW
9h 24m1 stop
$218Frontier
Find Deal
Tue, Nov 26 - Fri, Dec 6
6:48 pm - 12:31 amMDW-BOS
4h 43m1 stop
6:00 am - 5:18 pmBOS-MDW
12h 18m1 stop
$228Frontier
Find Deal
Tue, Nov 26 - Thu, Dec 5
8:25 pm - 11:35 pmMDW-BOS
2h 10mnonstop
6:00 pm - 7:45 pmBOS-MDW
2h 45mnonstop
$303Southwest
Find Deal
Tue, Nov 26 - Tue, Dec 3
5:25 am - 11:35 amMDW-BOS
5h 10m1 stop
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
$312Southwest
Find Deal
Tue, Nov 26 - Tue, Dec 3
3:19 pm - 11:42 pmMDW-BOS
7h 23m1 stop
5:20 am - 8:58 amBOS-MDW
4h 38m1 stop
$341Delta
Find Deal
Tue, Nov 26 - Sun, Dec 8
4:55 pm - 12:58 amMDW-BOS
7h 03m1 stop
8:00 am - 1:35 pmBOS-MDW
6h 35m1 stop
$346Delta
Find Deal
Sat, Nov 23 - Wed, Nov 27
9:21 am - 8:50 pmMDW-BOS
34h 29m3 stops
10:38 am - 8:45 amBOS-MDW
23h 07m3 stops
Tue, Nov 26 - Tue, Dec 3
10:10 am - 8:04 amMDW-BOS
20h 54m2 stops
10:38 am - 8:45 amBOS-MDW
23h 07m3 stops
Tue, Nov 26 - Tue, Dec 3
9:30 am - 12:11 pmMDW-PWM
25h 41m3 stops
6:10 am - 6:32 pmPWM-MDW
13h 22m3 stops
$1,639WestJet
Find Deal
Tue, Nov 26 - Sat, Nov 30
8:05 am - 11:20 amMDW-BOS
2h 15mnonstop
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
$158Southwest
Find Deal
Sat, Dec 7 - Thu, Dec 12
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
8:15 pm - 10:00 pmBOS-MDW
2h 45mnonstop
$179Southwest
Find Deal
Fri, Dec 13 - Sat, Jan 4
8:00 am - 11:15 amMDW-BOS
2h 15mnonstop
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
$188Southwest
Find Deal
Sun, Dec 8 - Tue, Jan 7
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
8:00 pm - 9:45 pmBOS-MDW
2h 45mnonstop
$195Southwest
Find Deal
Wed, Dec 25 - Sun, Dec 29
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
6:25 am - 8:15 amBOS-MDW
2h 50mnonstop
$199Southwest
Find Deal
Wed, Dec 18 - Sun, Dec 29
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
5:50 am - 7:50 amBOS-MDW
3h 00mnonstop
$208Southwest
Find Deal
Wed, Dec 25 - Sat, Jan 11
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
$218Southwest
Find Deal
Wed, Dec 18 - Wed, Dec 25
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
$238Southwest
Find Deal
Wed, Dec 4 - Thu, Dec 5
8:25 pm - 11:35 pmMDW-BOS
2h 10mnonstop
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
$247Southwest
Find Deal
Mon, Dec 23 - Thu, Jan 23
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
$248Southwest
Find Deal
Tue, Dec 3 - Wed, Dec 4

Frontier flights from Chicago Midway Airport to Maine

Our best Frontier deals on Chicago Midway Airport to Maine flight tickets
Frontier
Dec 11
MDW12:57 pmChicago Midway
10h 33m
1 stop
BOS12:30 amBoston Logan Intl
Dec 18
BOS5:45 amBoston Logan Intl
8h 39m
1 stop
MDW1:24 pmChicago Midway
Frontier
Dec 10
MDW12:57 pmChicago Midway
10h 33m
1 stop
BOS12:30 amBoston Logan Intl
Dec 11
BOS6:00 amBoston Logan Intl
6h 42m
1 stop
MDW11:42 amChicago Midway
Frontier
Jan 21
MDW5:31 pmChicago Midway
6h 08m
1 stop
BOS12:39 amBoston Logan Intl
Jan 28
BOS6:00 amBoston Logan Intl
11h 16m
1 stop
MDW4:16 pmChicago Midway

Southwest flights from Chicago Midway Airport to Maine

Our best Southwest deals on Chicago Midway Airport to Maine flight tickets
Southwest
Dec 13
MDW8:30 pmChicago Midway
2h 10m
BOS11:40 pmBoston Logan Intl
Dec 15
BOS6:40 amBoston Logan Intl
2h 45m
MDW8:25 amChicago Midway
Southwest
Nov 28
MDW8:10 amChicago Midway
2h 15m
BOS11:25 amBoston Logan Intl
Dec 7
BOS5:05 amBoston Logan Intl
2h 50m
MDW6:55 amChicago Midway
Southwest
Dec 13
MDW8:30 pmChicago Midway
2h 10m
BOS11:40 pmBoston Logan Intl
Jan 4
BOS8:15 pmBoston Logan Intl
2h 45m
MDW10:00 pmChicago Midway

See travel insights to Maine from

How to get the cheapest flight ticket from Chicago Midway Airport to Maine

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Maine?

The cheapest day to depart from Chicago Midway Airport to Maine is on a Wednesday. Travelers who choose to depart for Maine on a Wednesday will often find tickets for as low as $0. Flights from Chicago Midway Airport to Maine on a Friday will generally be more expensive and average around $506. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest Chicago Midway to Maine flight route?

Fly from Chicago Midway to Portland for the best Chicago Midway - Maine flight prices

What cabin class options are available on Chicago Midway to Maine flights?

There are 1 cabin classes available to choose from on Chicago Midway to Maine flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Maine flights?

You could potentially save up to 34% on your flight if you consider stops on a Chicago Midway Airport to Maine flight.

Cheap Chicago Midway Airport to Maine flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Maine

Best Price Found

$52

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Maine

2 airports
The best one-way flight to Maine from Chicago Midway Airport in the past 72 hours is $52. The best round-trip flight deal from Chicago Midway Airport to Maine found on momondo in the last 72 hours is $103.
The fastest flight from Chicago Midway Airport to Maine takes 2h 10m
Direct flights go from Chicago Midway Airport to Maine every day.
There are 2 airports near Maine: Boston Logan Intl (BOS), Portland (PWM)

  • When did momondo last update prices for flights from Chicago Midway Airport to Maine?

    Prices for flights from Chicago Midway Airport to Maine are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to Maine?

  • How old do you have to be to fly from Chicago Midway Airport to Maine?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Maine.

  • What documentation or ID do you need to fly to Maine?

    The travel and health documents required for your trip to Maine can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Maine. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago Midway Airport to Maine?


Best airlines flying from Chicago Midway Airport to Maine

Compare and see reviews for airlines that fly from Chicago Midway Airport to Maine with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $196Free CancellationRating
8.0
8,755 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Maine?

It is quick and easy to find Chicago to Maine flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Maine that suits you.

Can I find flights from Chicago to Maine with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Maine flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Maine?

momondo provides multiple filters to help you find the best flight to Maine from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Maine right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Maine flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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