Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Maine from $64

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 2/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago Midway Airport to Maine

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
1:20 pm - 1:03 am
MDW
-
BOS
10h 43m1 stop
Frontier Logo
6:00 am - 12:05 pm
BOS
-
MDW
7h 05m1 stop
$128Frontier
Wed, Jan 21 - Wed, Feb 4
Southwest Logo
6:40 am - 12:20 pm
MDW
-
BOS
4h 40m1 stop
Southwest Logo
2:40 pm - 4:30 pm
BOS
-
MDW
2h 50mnonstop
$131Southwest
Sat, Jan 17 - Sun, Jan 18
Southwest Logo
10:15 am - 1:30 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
$133Southwest
Sat, Feb 7 - Sun, Feb 8
Southwest Logo
2:00 pm - 5:10 pm
MDW
-
BOS
2h 10mnonstop
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
$136Southwest
Wed, Jan 14 - Sat, Jan 17
Southwest Logo
5:35 pm - 8:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
$137Southwest
Thu, Jan 22 - Mon, Jan 26
Southwest Logo
10:15 am - 1:30 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:50 am - 1:55 pm
BOS
-
MDW
9h 05m2 stops
$139Southwest
Sat, Jan 17 - Sun, Jan 18
Frontier Logo
1:20 pm - 1:03 am
MDW
-
BOS
10h 43m1 stop
Frontier Logo
6:00 am - 11:45 am
BOS
-
MDW
6h 45m1 stop
$145Frontier
Wed, Jan 28 - Mon, Feb 2
Delta Logo
1:26 pm - 11:22 pm
MDW
-
PWM
8h 56m2 stops
Delta Logo
12:20 pm - 5:55 pm
PWM
-
MDW
6h 35m1 stop
$234Delta
Thu, Jan 22 - Fri, Jan 23
Delta Logo
1:26 pm - 11:22 pm
MDW
-
PWM
8h 56m2 stops
Delta Logo
12:43 pm - 10:22 pm
PWM
-
MDW
10h 39m2 stops
$239Delta
Thu, Jan 22 - Fri, Jan 23
Delta Logo
12:45 pm - 11:20 pm
MDW
-
PWM
9h 35m2 stops
Delta Logo
6:00 am - 12:46 pm
PWM
-
MDW
7h 46m2 stops
$259Delta
Wed, Feb 25 - Fri, Feb 27

Frontier flights from Chicago Midway Airport to Maine

Our best Frontier deals on Chicago Midway Airport to Maine flight tickets
Frontier
Jan 21
MDW1:20 pmChicago Midway
10h 43m
1 stop
BOS1:03 amBoston Logan Intl
Feb 4
BOS6:00 amBoston Logan Intl
7h 05m
1 stop
MDW12:05 pmChicago Midway
$128
Find similar
Frontier
Jan 28
MDW1:20 pmChicago Midway
10h 43m
1 stop
BOS1:03 amBoston Logan Intl
Feb 2
BOS6:00 amBoston Logan Intl
6h 45m
1 stop
MDW11:45 amChicago Midway
$145
Find similar
Frontier
Jan 29
MDW5:01 pmChicago Midway
7h 12m
1 stop
BOS1:13 amBoston Logan Intl
Feb 2
BOS6:00 amBoston Logan Intl
6h 45m
1 stop
MDW11:45 amChicago Midway
$163
Find similar

Southwest flights from Chicago Midway Airport to Maine

Our best Southwest deals on Chicago Midway Airport to Maine flight tickets
Southwest
Jan 17
MDW12:15 pmChicago Midway
6h 10m
1 stop
BOS7:25 pmBoston Logan Intl
Jan 18
BOS5:30 amBoston Logan Intl
2h 50m
MDW7:20 amChicago Midway
$131
Find similar
Southwest
Feb 7
MDW10:15 amChicago Midway
2h 15m
BOS1:30 pmBoston Logan Intl
Feb 10
BOS2:40 pmBoston Logan Intl
2h 50m
MDW4:30 pmChicago Midway
$133
Find similar
Southwest
Jan 22
MDW5:35 pmChicago Midway
2h 15m
BOS8:50 pmBoston Logan Intl
Jan 26
BOS5:30 amBoston Logan Intl
2h 50m
MDW7:20 amChicago Midway
$137
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Maine that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 27, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 1/21

1:20 pm-1:03 am

1 stop10h 43m

Boston Logan Intl

Wed 2/4

6:00 am-12:05 pm

1 stop7h 05m

$128

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 1/17

6:40 am-12:20 pm

1 stop4h 40m

Boston Logan Intl

Sun 1/18

2:40 pm-4:30 pm

Nonstop2h 50m

$131

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 2/7

10:15 am-1:30 pm

Nonstop2h 15m

Boston Logan Intl

Sun 2/8

5:30 am-7:20 am

Nonstop2h 50m

$133

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 1/14

2:00 pm-5:10 pm

Nonstop2h 10m

Boston Logan Intl

Sat 1/17

5:30 am-7:20 am

Nonstop2h 50m

$136

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 1/22

5:35 pm-8:50 pm

Nonstop2h 15m

Boston Logan Intl

Mon 1/26

5:30 am-7:20 am

Nonstop2h 50m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 1/17

10:15 am-1:30 pm

Nonstop2h 15m

Boston Logan Intl

Sun 1/18

5:50 am-1:55 pm

2 stops9h 05m

$139

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 1/28

1:20 pm-1:03 am

1 stop10h 43m

Boston Logan Intl

Mon 2/2

6:00 am-11:45 am

1 stop6h 45m

$145

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 1/22

1:26 pm-11:22 pm

2 stops8h 56m

Portland

Fri 1/23

12:20 pm-5:55 pm

1 stop6h 35m

$234

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 1/22

1:26 pm-11:22 pm

2 stops8h 56m

Portland

Fri 1/23

12:43 pm-10:22 pm

2 stops10h 39m

$239

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 2/25

12:45 pm-11:20 pm

2 stops9h 35m

Portland

Fri 2/27

6:00 am-12:46 pm

2 stops7h 46m

$259

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 Tuesday. Travelers who choose to depart for Maine on a Tuesday will often find tickets for as low as $259. Flights from Chicago Midway Airport to Maine on a Thursday will generally be more expensive and average around $477. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

The cheapest time of day to fly to Maine is at noon when flights can be purchased for as low as $372. Flights in the morning are often more expensive with an average ticket price of $411.

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 is only 1 cabin class 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 50% 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

Fastest flight time

2h 10m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

Airports in Maine

49 airports
The fastest flight from Chicago Midway Airport to Maine takes 2h 10m
Direct flights go from Chicago Midway Airport to Maine on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There are 49 airports in Maine. From Chicago Midway Airport there are direct flights to Boston Logan Intl (BOS), Portland (PWM).
Search flight deals

  • 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
SouthwestPriceFrom $313Free CancellationRating
8.0
4,258 reviews
Search Southwest 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.

An easier way to manage your Maine trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 1/26
Mon 2/2
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Maine

Popular cities in Maine

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $50
Flights to Los Angelesfrom $47
Flights to Miamifrom $50
Flights to Chicagofrom $51
Flights to Orlandofrom $49
Flights to San Franciscofrom $59
Flights to Las Vegasfrom $49
Flights to Washington, D.C.from $58
Flights to Bostonfrom $51
Flights to Atlantafrom $44
Flights to Dallasfrom $51
Flights to Seattlefrom $57