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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 2/5. 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 - 4:16 pmBOS-MDW
11h 16m1 stop
4:20 pm - 12:31 amMDW-BOS
7h 11m1 stop
$108Frontier
Find Deal
mar., feb. 4 - mié., feb. 12
12:56 pm - 10:39 pmBOS-MDW
10h 43m1 stop
4:20 pm - 12:31 amMDW-BOS
7h 11m1 stop
$109Frontier
Find Deal
lun., feb. 10 - mié., feb. 12
5:10 am - 11:34 amBOS-MDW
7h 24m1 stop
3:14 pm - 12:31 amMDW-BOS
8h 17m1 stop
$110Frontier
Find Deal
lun., mar. 10 - mié., mar. 12
12:16 pm - 12:09 pmBOS-MDW
24h 53m1 stop
11:33 am - 12:27 amMDW-BOS
11h 54m1 stop
$111Frontier
Find Deal
jue., ene. 23 - lun., ene. 27
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
6:25 pm - 9:40 pmMDW-BOS
2h 15mnonstop
$137Southwest
Find Deal
jue., ene. 23 - lun., ene. 27
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
6:25 pm - 9:40 pmMDW-BOS
2h 15mnonstop
$147Southwest
Find Deal
lun., ene. 27 - vie., ene. 31
6:00 am - 2:42 pmBOS-MDW
9h 42m1 stop
12:26 pm - 8:28 amMDW-BOS
19h 02m1 stop
vie., feb. 7 - vie., feb. 14
5:35 pm - 11:29 pmBOS-MDW
30h 54m2 stops
12:26 pm - 8:28 amMDW-BOS
19h 02m1 stop
vie., feb. 7 - vie., feb. 14
6:00 am - 5:43 pmPWM-MDW
12h 43m2 stops
12:44 pm - 11:10 pmMDW-PWM
9h 26m2 stops
$249Delta
Find Deal
vie., feb. 7 - lun., feb. 10
5:34 am - 11:59 amPWM-MDW
7h 25m1 stop
12:44 pm - 11:10 pmMDW-PWM
9h 26m2 stops
$254Delta
Find Deal
vie., ene. 24 - lun., ene. 27
6:00 am - 7:06 pmBOS-MDW
14h 06m1 stop
$52Frontier
Find Deal
mié., feb. 5
5:10 am - 11:34 amBOS-MDW
7h 24m1 stop
$55Frontier
Find Deal
lun., mar. 10
6:00 am - 4:16 pmBOS-MDW
11h 16m1 stop
$56Frontier
Find Deal
mar., feb. 11
6:00 am - 4:16 pmBOS-MDW
11h 16m1 stop
$57Frontier
Find Deal
mar., ene. 28
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
$69Southwest
Find Deal
mié., feb. 12
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
$79Southwest
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dom., feb. 9
5:34 am - 11:59 amPWM-MDW
7h 25m1 stop
$115Delta
Find Deal
vie., feb. 7
5:27 am - 12:42 pmPWM-MDW
8h 15m2 stops
$120Delta
Find Deal
jue., feb. 6
6:10 am - 3:29 pmBOS-MDW
34h 19m3 stops
mié., abr. 16
10:03 am - 5:30 pmBOS-MDW
32h 27m3 stops
mié., feb. 26
6:00 am - 3:33 pmBOS-MDW
10h 33m1 stop
4:19 pm - 12:30 amMDW-BOS
7h 11m1 stop
$230Frontier
Find Deal
lun., ene. 13 - sáb., feb. 15
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
6:25 am - 9:40 amMDW-BOS
2h 15mnonstop
$273Southwest
Find Deal
lun., ene. 13 - sáb., feb. 15
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
6:00 am - 11:55 amMDW-BOS
4h 55m1 stop
$283Southwest
Find Deal
lun., ene. 13 - sáb., feb. 15
6:00 am - 4:14 pmBOS-MDW
11h 14m1 stop
12:51 pm - 12:39 amMDW-BOS
10h 48m1 stop
$290Frontier
Find Deal
mar., ene. 14 - vie., ene. 17
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
8:40 am - 11:55 amMDW-BOS
2h 15mnonstop
$297Southwest
Find Deal
lun., ene. 13 - jue., ene. 16
6:00 am - 3:33 pmBOS-MDW
10h 33m1 stop
5:24 pm - 12:30 amMDW-BOS
6h 06m1 stop
$310Frontier
Find Deal
lun., ene. 13 - mar., ene. 14
8:30 am - 5:20 pmBOS-MDW
9h 50m2 stops
6:00 am - 11:55 amMDW-BOS
4h 55m1 stop
$318Southwest
Find Deal
lun., ene. 13 - sáb., feb. 15
5:23 am - 12:46 pmPWM-MDW
8h 23m2 stops
5:07 pm - 11:51 pmMDW-PWM
5h 44m1 stop
$424Delta
Find Deal
dom., ene. 12 - mié., ene. 15
5:23 am - 12:46 pmPWM-MDW
8h 23m2 stops
6:00 am - 4:44 pmMDW-PWM
9h 44m2 stops
$429Delta
Find Deal
dom., ene. 12 - mié., ene. 15
5:20 am - 8:54 amBOS-MDW
4h 34m1 stop
6:00 am - 1:39 pmMDW-BOS
6h 39m1 stop
$677Delta
Find Deal
mar., ene. 14 - mié., ene. 15
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
9:00 am - 12:15 pmMDW-BOS
2h 15mnonstop
$137Southwest
Find Deal
jue., ene. 23 - sáb., ene. 25
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
6:25 pm - 9:40 pmMDW-BOS
2h 15mnonstop
$147Southwest
Find Deal
lun., ene. 27 - vie., ene. 31
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
8:40 am - 11:55 amMDW-BOS
2h 15mnonstop
$157Southwest
Find Deal
vie., ene. 31 - dom., feb. 2
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
6:55 pm - 10:10 pmMDW-BOS
2h 15mnonstop
$168Southwest
Find Deal
mar., feb. 4 - sáb., feb. 15
7:00 am - 8:55 amBOS-MDW
2h 55mnonstop
8:40 am - 11:55 amMDW-BOS
2h 15mnonstop
$177Southwest
Find Deal
vie., feb. 7 - lun., feb. 10
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
8:40 am - 11:55 amMDW-BOS
2h 15mnonstop
$187Southwest
Find Deal
jue., ene. 30 - dom., feb. 2
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
6:25 am - 9:40 amMDW-BOS
2h 15mnonstop
$188Southwest
Find Deal
mié., feb. 12 - sáb., feb. 22
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
6:25 pm - 9:40 pmMDW-BOS
2h 15mnonstop
$192Southwest
Find Deal
dom., ene. 19 - mar., ene. 28
8:05 pm - 9:55 pmBOS-MDW
2h 50mnonstop
8:40 pm - 11:55 pmMDW-BOS
2h 15mnonstop
$197Southwest
Find Deal
vie., mar. 21 - dom., mar. 23
6:50 am - 8:45 amBOS-MDW
2h 55mnonstop
8:20 pm - 11:35 pmMDW-BOS
2h 15mnonstop
$199Southwest
Find Deal
jue., feb. 13 - lun., feb. 17

Frontier flights from Maine to Chicago Midway Airport

Our best Frontier deals on Maine to Chicago Midway Airport flight tickets
Frontier
Feb 4
BOS6:00 amBoston Logan Intl
11h 16m
1 stop
MDW4:16 pmChicago Midway
Feb 12
MDW4:20 pmChicago Midway
7h 11m
1 stop
BOS12:31 amBoston Logan Intl
Frontier
Feb 10
BOS12:56 pmBoston Logan Intl
10h 43m
1 stop
MDW10:39 pmChicago Midway
Feb 12
MDW4:20 pmChicago Midway
7h 11m
1 stop
BOS12:31 amBoston Logan Intl
Frontier
Mar 10
BOS5:10 amBoston Logan Intl
7h 24m
1 stop
MDW11:34 amChicago Midway
Mar 12
MDW3:14 pmChicago Midway
8h 17m
1 stop
BOS12:31 amBoston Logan Intl

Southwest flights from Maine to Chicago Midway Airport

Our best Southwest deals on Maine to Chicago Midway Airport flight tickets
Southwest
Jan 23
BOS5:40 pmBoston Logan Intl
2h 50m
MDW7:30 pmChicago Midway
Jan 27
MDW6:25 pmChicago Midway
2h 15m
BOS9:40 pmBoston Logan Intl
Southwest
Jan 27
BOS8:10 amBoston Logan Intl
2h 55m
MDW10:05 amChicago Midway
Jan 31
MDW6:25 pmChicago Midway
2h 15m
BOS9:40 pmBoston Logan Intl
Southwest
Jan 23
BOS8:10 amBoston Logan Intl
2h 55m
MDW10:05 amChicago Midway
Jan 24
MDW6:25 pmChicago Midway
2h 15m
BOS9:40 pmBoston Logan Intl

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.

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 35m

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 $108.
The fastest flight from Maine to Chicago Midway Airport takes 2h 35m
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
8,501 reviews
Search Delta flights
SouthwestPriceFrom $281Free CancellationRating
8.1
4,650 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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