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Cheap flights from Maine to Chicago Midway Airport 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 Maine to Chicago Midway Airport departing on 12/17. 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 Maine to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Maine to Chicago 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 Maine to Chicago.

Cheap last minute flights

Planning a quick getaway from Maine to Chicago? 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 Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Maine to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
6:00 am - 5:54 pmBOS-MDW
12h 54m1 stop
10:50 am - 12:39 amMDW-BOS
12h 49m1 stop
$100Frontier
Find Deal
Tue, Dec 17 - Wed, Dec 18
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
6:49 pm - 12:39 amMDW-BOS
28h 50m1 stop
$104Frontier
Find Deal
Tue, Dec 10 - Tue, Dec 17
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
$158Southwest
Find Deal
Thu, Dec 12 - Mon, Dec 16
5:10 am - 7:00 amBOS-MDW
2h 50mnonstop
10:05 am - 1:20 pmMDW-BOS
2h 15mnonstop
$179Southwest
Find Deal
Sat, Jan 4 - Wed, Jan 8
5:34 am - 11:59 amPWM-MDW
7h 25m1 stop
9:34 am - 4:06 pmMDW-PWM
5h 32m1 stop
$228Delta
Find Deal
Tue, Jan 21 - Fri, Jan 31
6:00 am - 5:47 pmPWM-MDW
12h 47m2 stops
9:34 am - 4:06 pmMDW-PWM
5h 32m1 stop
$233Delta
Find Deal
Wed, Jan 8 - Sat, Jan 11
12:01 pm - 6:32 pmPWM-MDW
31h 31m3 stops
9:38 am - 4:35 pmMDW-PWM
29h 57m3 stops
Mon, Dec 9 - Wed, Dec 11
4:30 pm - 1:31 pmPWM-MDW
22h 01m3 stops
2:15 pm - 11:49 amMDW-PWM
20h 34m3 stops
$1,405WestJet
Find Deal
Thu, Dec 12 - Sun, Dec 15
4:30 pm - 1:31 pmPWM-MDW
22h 01m3 stops
2:15 pm - 11:49 amMDW-PWM
20h 34m3 stops
$1,408WestJet
Find Deal
Thu, Dec 12 - Sun, Dec 15
1:55 pm - 1:31 pmPWM-MDW
24h 36m3 stops
9:38 am - 4:35 pmMDW-PWM
29h 57m3 stops
$1,417
Find Deal
Sat, Dec 7 - Wed, Dec 11
8:01 am - 1:09 pmBOS-MDW
6h 08m1 stop
$52Frontier
Find Deal
Tue, Dec 17
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
$53Frontier
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Wed, Dec 11
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
$79Southwest
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Wed, Feb 5
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
$89Southwest
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Tue, Feb 25
5:05 am - 8:50 amPWM-MDW
4h 45m1 stop
$114Delta
Find Deal
Wed, Dec 25
6:00 am - 5:47 pmPWM-MDW
12h 47m2 stops
$119Delta
Find Deal
Tue, Jan 7
10:44 am - 5:30 pmBOS-MDW
31h 46m3 stops
Wed, Feb 26
12:35 pm - 5:51 pmBOS-MDW
30h 16m3 stops
Wed, Jan 1
5:25 pm - 5:47 pmPWM-MDW
25h 22m3 stops
$356WestJet
Find Deal
Thu, Jan 9
5:25 pm - 5:47 pmPWM-MDW
25h 22m3 stops
$367WestJet
Find Deal
Thu, Jan 9
5:45 pm - 11:15 pmBOS-MDW
6h 30m1 stop
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
$275Southwest
Find Deal
Mon, Dec 2 - Fri, Dec 6
11:35 am - 9:59 pmBOS-MDW
11h 24m1 stop
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
$278Frontier
Find Deal
Thu, Nov 28 - Wed, Dec 4
6:30 am - 8:15 amBOS-MDW
2h 45mnonstop
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
$283Southwest
Find Deal
Thu, Nov 28 - Wed, Dec 4
12:37 pm - 7:32 pmBOS-MDW
7h 55m1 stop
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
$301Frontier
Find Deal
Mon, Dec 2 - Tue, Dec 10
12:10 pm - 4:10 pmBOS-MDW
5h 00m1 stop
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
$312Southwest
Find Deal
Thu, Nov 28 - Wed, Dec 4
5:45 pm - 11:15 pmBOS-MDW
6h 30m1 stop
6:20 am - 3:30 pmMDW-BOS
8h 10m1 stop
$319Southwest
Find Deal
Mon, Dec 2 - Wed, Dec 4
5:45 pm - 11:15 pmBOS-MDW
6h 30m1 stop
1:30 pm - 10:10 pmMDW-BOS
7h 40m1 stop
$331Southwest
Find Deal
Mon, Dec 2 - Wed, Dec 4
5:20 am - 8:50 amBOS-MDW
4h 30m1 stop
9:31 am - 3:50 pmMDW-BOS
5h 19m1 stop
$339Delta
Find Deal
Sat, Nov 30 - Tue, Dec 3
5:00 am - 8:50 amPWM-MDW
4h 50m1 stop
1:30 pm - 11:47 pmMDW-PWM
9h 17m2 stops
$363Delta
Find Deal
Sat, Nov 30 - Wed, Dec 4
6:10 am - 6:32 pmPWM-MDW
13h 22m3 stops
9:30 am - 11:35 amMDW-PWM
25h 05m3 stops
$1,655WestJet
Find Deal
Sun, Dec 1 - Tue, Dec 3
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
$158Southwest
Find Deal
Thu, Dec 12 - Mon, Dec 16
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
6:25 pm - 9:40 pmMDW-BOS
2h 15mnonstop
$168Southwest
Find Deal
Wed, Feb 5 - Wed, Feb 26
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
5:00 pm - 8:10 pmMDW-BOS
2h 10mnonstop
$178Southwest
Find Deal
Wed, Jan 8 - Sat, Jan 11
5:10 am - 7:00 amBOS-MDW
2h 50mnonstop
10:05 am - 1:20 pmMDW-BOS
2h 15mnonstop
$179Southwest
Find Deal
Sat, Jan 4 - Wed, Jan 8
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
$188Southwest
Find Deal
Thu, Dec 12 - Sun, Dec 15
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
8:25 pm - 11:35 pmMDW-BOS
2h 10mnonstop
$195Southwest
Find Deal
Wed, Jan 1 - Sun, Jan 5
12:05 pm - 1:50 pmBOS-MDW
2h 45mnonstop
8:25 pm - 11:35 pmMDW-BOS
2h 10mnonstop
$199Southwest
Find Deal
Sat, Dec 7 - Sat, Jan 4
6:40 am - 8:25 amBOS-MDW
2h 45mnonstop
8:25 pm - 11:35 pmMDW-BOS
2h 10mnonstop
$200Southwest
Find Deal
Fri, Jan 3 - Sun, Jan 5
6:40 am - 8:25 amBOS-MDW
2h 45mnonstop
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
$218Southwest
Find Deal
Fri, Dec 13 - Sun, Dec 15
6:25 am - 8:15 amBOS-MDW
2h 50mnonstop
8:00 am - 11:15 amMDW-BOS
2h 15mnonstop
$220Southwest
Find Deal
Sun, Dec 29 - Fri, Jan 3

Frontier flights from Maine to Chicago Midway Airport

Our best Frontier deals on Maine to Chicago Midway Airport flight tickets
Frontier
Dec 17
BOS6:00 amBoston Logan Intl
12h 54m
1 stop
MDW5:54 pmChicago Midway
Dec 18
MDW10:50 amChicago Midway
12h 49m
1 stop
BOS12:39 amBoston Logan Intl
Frontier
Dec 10
BOS6:00 amBoston Logan Intl
6h 42m
1 stop
MDW11:42 amChicago Midway
Dec 17
MDW6:49 pmChicago Midway
28h 50m
1 stop
BOS12:39 amBoston Logan Intl
Frontier
Dec 11
BOS6:00 amBoston Logan Intl
6h 42m
1 stop
MDW11:42 amChicago Midway
Jan 14
MDW5:24 pmChicago Midway
6h 06m
1 stop
BOS12:30 amBoston Logan Intl

Delta flights from Maine to Chicago Midway Airport

Our best Delta deals on Maine to Chicago Midway Airport flight tickets
Delta
Jan 21
PWM5:34 amPortland
7h 25m
1 stop
MDW11:59 amChicago Midway
Jan 31
MDW9:34 amChicago Midway
5h 32m
1 stop
PWM4:06 pmPortland
Delta
Jan 8
PWM6:00 amPortland
12h 47m
2 stops
MDW5:47 pmChicago Midway
Jan 11
MDW9:34 amChicago Midway
5h 32m
1 stop
PWM4:06 pmPortland
Delta
Jan 8
PWM6:00 amPortland
12h 47m
2 stops
MDW5:47 pmChicago Midway
Jan 11
MDW9:34 amChicago Midway
8h 50m
2 stops
PWM7:24 pmPortland

See travel insights to Chicago from

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

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 Chicago Midway Airport?

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Maine. The lowest ticket price found for a Thursday departure recently was $387. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Tuesday is the most expensive day to depart from Maine because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $497.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Maine in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $347 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $417. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Maine to Chicago Midway flight route?

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

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

There are 1 cabin classes available to choose from on Maine to Chicago Midway 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 Maine to Chicago Midway Airport flights?

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

Cheap Maine to Chicago Midway Airport flight deals and tips

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

Best Price Found

$52

Fastest flight time

2h 45m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Maine in the past 72 hours is $52. The best round-trip flight deal from Maine to Chicago Midway Airport found on momondo in the last 72 hours is $100.
The fastest flight from Maine to Chicago Midway Airport takes 2h 45m
Direct flights go from Maine to Chicago Midway Airport every day.

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

    Prices for flights from Maine to Chicago Midway Airport are updated daily.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Maine to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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


Best airlines flying from Maine to Chicago Midway Airport

Compare and see reviews for airlines that fly from Maine to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $201Free CancellationRating
8.0
8,730 reviews
Search Delta flights
SouthwestPriceFrom $281Free CancellationRating
8.1
4,979 reviews
Search Southwest flights

Why use momondo?

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

Finding the right flight to Chicago from Maine is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Chicago from Maine with this policy.

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

Once you have performed a search for Maine to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Chicago from Maine. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


An easier way to manage your Chicago Midway Airport trip

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