What is the cheapest airline that flies from Chicago Midway to Maine?

Southwest, Delta, and Allegiant Air are the most popular carriers operating from Chicago Midway to Maine

How many flights depart from Chicago Midway Airport to Maine on average per day?

As of April 2026, there are 1 flights per day flying from Chicago Midway Airport to Maine. The most common time of day flights depart is 8:00AM, with 100% of flights taking off at noon.

How many flights depart from Chicago Midway Airport to Maine on average per week?

13 flights are operational weekly from Chicago Midway Airport to Maine as of April 2026. The most popular departure day for this route is Mon, with 38% of flights per week taking off on this day.

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?

As of April 2026, there is 1 operator available to choose from 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.

$74 Cheap Flights from Chicago Midway Airport to Maine in 2026

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Find the cheapest flights from Chicago Midway Airport to Maine

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:15 pm - 1:31 am

MDW

BOS

10h 16m

1 stop

12:01 pm - 10:02 pm

BOS

MDW

11h 01m

1 stop

$140Frontier

Wed, Apr 29 - Wed, May 6

4:52 pm - 9:12 am

MDW

BOS

15h 20m

1 stop

6:00 am - 11:09 am

BOS

MDW

6h 09m

1 stop

$141Frontier

Fri, May 8 - Mon, May 11

2:15 pm - 1:31 am

MDW

BOS

10h 16m

1 stop

12:52 pm - 7:31 pm

BOS

MDW

7h 39m

1 stop

$144Frontier

Tue, Apr 21 - Tue, Apr 28

2:15 pm - 1:31 am

MDW

BOS

10h 16m

1 stop

6:00 am - 7:31 pm

BOS

MDW

14h 31m

1 stop

$147Frontier

Tue, Apr 21 - Wed, Apr 22

7:00 pm - 10:20 pm

MDW

BOS

2h 20mnonstop

6:10 am - 7:55 am

BOS

MDW

2h 45mnonstop

$157Southwest

Thu, Apr 30 - Sun, May 3

2:15 pm - 1:31 am

MDW

BOS

10h 16m

1 stop

8:16 pm - 10:19 pm

BOS

MDW

27h 03m

2 stops

$164Multiple Airlines

Tue, Apr 21 - Wed, Apr 22

9:00 am - 4:05 pm

MDW

BOS

6h 05m

1 stop

6:10 am - 7:55 am

BOS

MDW

2h 45mnonstop

$167Southwest

Thu, Apr 30 - Sun, May 3

2:15 pm - 7:13 pm

MDW

BGR

27h 58m

2 stops

7:53 pm - 8:04 am

BGR

MDW

13h 11m

1 stop

$347Multiple Airlines

Wed, Apr 15 - Sun, Apr 19

12:53 pm - 11:33 pm

MDW

BGR

9h 40m

2 stops

5:05 am - 4:16 pm

BGR

MDW

12h 11m

2 stops

$363Delta

Wed, Jun 3 - Wed, Jun 10

9:27 am - 7:52 pm

MDW

BGR

9h 25m

2 stops

5:15 am - 12:43 pm

BGR

MDW

8h 28m

2 stops

$369Delta

Sat, Apr 18 - Wed, Apr 22

Frontier flights from Chicago Midway Airport to Maine

Our best Frontier deals on Chicago Midway Airport to Maine flight tickets

Frontier

Apr 29

MDW2:15 pmChicago Midway

10h 16m

1 stop

BOS1:31 amBoston Logan Intl

May 5

BOS6:00 amBoston Logan Intl

6h 12m

1 stop

MDW11:12 amChicago Midway

$140

Frontier

May 8

MDW4:52 pmChicago Midway

15h 20m

1 stop

BOS9:12 amBoston Logan Intl

May 11

BOS6:00 amBoston Logan Intl

6h 09m

1 stop

MDW11:09 amChicago Midway

$141

Frontier

Apr 21

MDW2:15 pmChicago Midway

10h 16m

1 stop

BOS1:31 amBoston Logan Intl

Apr 28

BOS12:52 pmBoston Logan Intl

7h 39m

1 stop

MDW7:31 pmChicago Midway

$144

Southwest flights from Chicago Midway Airport to Maine

Our best Southwest deals on Chicago Midway Airport to Maine flight tickets

Southwest

Apr 16

MDW9:25 amChicago Midway

2h 15m

BOS12:40 pmBoston Logan Intl

Apr 23

BOS3:45 pmBoston Logan Intl

2h 45m

MDW5:30 pmChicago Midway

$157

Southwest

Apr 30

MDW9:00 amChicago Midway

6h 05m

1 stop

BOS4:05 pmBoston Logan Intl

May 3

BOS6:10 amBoston Logan Intl

2h 45m

MDW7:55 amChicago Midway

$167

Southwest

May 2

MDW7:45 amChicago Midway

2h 15m

BOS11:00 amBoston Logan Intl

May 3

BOS6:10 amBoston Logan Intl

2h 45m

MDW7:55 amChicago Midway

$172

momondo Fare Finder

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

Cheapest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 4/29

2:15 pm-1:31 am

1 stop10h 16m

Boston Logan Intl

Wed 5/6

12:01 pm-10:02 pm

1 stop11h 01m

$140

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 5/8

4:52 pm-9:12 am

1 stop15h 20m

Boston Logan Intl

Mon 5/11

6:00 am-11:09 am

1 stop6h 09m

$141

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 4/21

2:15 pm-1:31 am

1 stop10h 16m

Boston Logan Intl

Tue 4/28

12:52 pm-7:31 pm

1 stop7h 39m

$144

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 4/21

2:15 pm-1:31 am

1 stop10h 16m

Boston Logan Intl

Wed 4/22

6:00 am-7:31 pm

1 stop14h 31m

$147

Quickest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 4/30

7:00 pm-10:20 pm

Nonstop2h 20m

Boston Logan Intl

Sun 5/3

6:10 am-7:55 am

Nonstop2h 45m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 4/21

2:15 pm-1:31 am

1 stop10h 16m

Boston Logan Intl

Wed 4/22

8:16 pm-10:19 pm

2 stops27h 03m

$164

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 4/30

9:00 am-4:05 pm

1 stop6h 05m

Boston Logan Intl

Sun 5/3

6:10 am-7:55 am

Nonstop2h 45m

$167

ChicagoBangor

MDW - BGR

MDWBGR

Chicago Midway

Wed 4/15

2:15 pm-7:13 pm

2 stops27h 58m

Bangor

Sun 4/19

7:53 pm-8:04 am

1 stop13h 11m

$347

ChicagoBangor

MDW - BGR

MDWBGR

Chicago Midway

Wed 6/3

12:53 pm-11:33 pm

2 stops9h 40m

Bangor

Wed 6/10

5:05 am-4:16 pm

2 stops12h 11m

$363

ChicagoBangor

MDW - BGR

MDWBGR

Chicago Midway

Sat 4/18

9:27 am-7:52 pm

2 stops9h 25m

Bangor

Wed 4/22

5:15 am-12:43 pm

2 stops8h 28m

$369

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

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 $245. 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 $387. Flights in the morning are often more expensive with an average ticket price of $410.

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 75% 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	Every day
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 every day.

There are 49 airports in Maine. From Chicago Midway Airport there are direct flights to Portland (PWM), Boston Logan Intl (BOS).

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Maine

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?
As of April 2026, there is 1 operator available to choose from 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?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Maine is Boeing 737 MAX 8, representing 14.29% of all bookings. The subsequent popular models are Boeing 737-800 at 14.29%, Embraer 170 at 14.29%, and Airbus A319 at 7.14%.

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
Southwest	PriceFrom $259	Free Cancellation	Rating 8.0 4,343 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.