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

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

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

1 flights are operational weekly from Chicago Midway Airport to Maine as of October 2026. The most popular departure day for this route is Wed, with 100% 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 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.

$157 Cheap Flights from Chicago Midway Airport to Maine in 2026/27

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.

4:10 pm - 7:25 pmMDW Chicago Midway-PWM Portland

2h 15mnonstop

6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway

2h 35mnonstop

$353Southwest

Sat, Oct 24 - Wed, Oct 28

6:40 pm - 9:55 pmMDW Chicago Midway-PWM Portland

2h 15mnonstop

6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway

2h 35mnonstop

$353Southwest

Mon, Oct 26 - Wed, Oct 28

6:40 pm - 9:55 pmMDW Chicago Midway-PWM Portland

2h 15mnonstop

6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway

2h 35mnonstop

$353Southwest

Mon, Oct 26 - Tue, Oct 27

6:25 pm - 11:55 pmMDW Chicago Midway-PWM Portland

4h 30m1 stop Baltimore/Washington

6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway

2h 35mnonstop

$363Southwest

Mon, Oct 26 - Wed, Oct 28

6:45 am - 2:50 pmMDW Chicago Midway-PWM Portland

7h 05m1 stop Nashville Intl

6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway

2h 35mnonstop

$363Southwest

Sat, Oct 24 - Wed, Oct 28

7:45 am - 10:55 amMDW Chicago Midway-PWM Portland

2h 10mnonstop

12:45 pm - 6:55 pmPWM Portland-MDW Chicago Midway

7h 10m1 stop Baltimore/Washington

$363Southwest

Tue, Oct 27 - Wed, Nov 4

7:45 am - 10:55 amMDW Chicago Midway-PWM Portland

2h 10mnonstop

3:25 pm - 9:25 pmPWM Portland-MDW Chicago Midway

7h 00m1 stop Baltimore/Washington

$363Southwest

Tue, Oct 27 - Tue, Nov 3

6:40 pm - 9:55 pmMDW Chicago Midway-PWM Portland

2h 15mnonstop

5:40 am - 11:20 amPWM Portland-MDW Chicago Midway

6h 40m1 stop Baltimore/Washington

$363Southwest

Mon, Oct 26 - Tue, Oct 27

4:10 pm - 7:25 pmMDW Chicago Midway-PWM Portland

2h 15mnonstop

11:35 am - 4:55 pmPWM Portland-MDW Chicago Midway

6h 20m1 stop Nashville Intl

$363Southwest

Sat, Oct 24 - Tue, Oct 27

Cheap last minute flights

Enter your travel dates to find the best prices.

4:50 pm - 10:10 pmMDW Chicago Midway-PWM Portland

4h 20m1 stop Baltimore/Washington

6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway

2h 35mnonstop

$427Southwest

Sat, Oct 3 - Wed, Oct 7

11:55 am - 10:10 pmMDW Chicago Midway-PWM Portland

9h 15m2 stops Tampa Baltimore/Washington

6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway

2h 35mnonstop

$432Southwest

Sat, Oct 3 - Wed, Oct 7

1:19 pm - 11:56 pmMDW Chicago Midway-PWM Portland

9h 37m2 stops Detroit Metropolitan Wayne County New York John F Kennedy Intl

11:55 am - 4:47 pmPWM Portland-MDW Chicago Midway

5h 52m1 stop Minneapolis St Paul

$442Delta

Sat, Oct 3 - Wed, Oct 7

11:55 am - 10:10 pmMDW Chicago Midway-PWM Portland

9h 15m2 stops Tampa Baltimore/Washington

5:40 am - 2:40 pmPWM Portland-MDW Chicago Midway

10h 00m2 stops Baltimore/Washington Orlando

$462Southwest

Sat, Oct 3 - Wed, Oct 7

4:10 pm - 7:20 pmMDW Chicago Midway-PWM Portland

2h 10mnonstop

6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway

2h 35mnonstop

$467Southwest

Sat, Oct 3 - Wed, Oct 7

7:50 pm - 11:05 pmMDW Chicago Midway-PWM Portland

2h 15mnonstop

6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway

2h 35mnonstop

$467Southwest

Sun, Oct 4 - Tue, Oct 6

7:45 am - 10:55 amMDW Chicago Midway-PWM Portland

2h 10mnonstop

4:35 pm - 6:10 pmPWM Portland-MDW Chicago Midway

2h 35mnonstop

$467Southwest

Tue, Oct 6 - Sat, Oct 10

7:50 pm - 11:05 pmMDW Chicago Midway-PWM Portland

2h 15mnonstop

6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway

2h 35mnonstop

$467Southwest

Sun, Oct 4 - Wed, Oct 7

6:40 pm - 9:55 pmMDW Chicago Midway-PWM Portland

2h 15mnonstop

6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway

2h 35mnonstop

$467Southwest

Mon, Oct 5 - Tue, Oct 6

4:10 pm - 7:20 pmMDW Chicago Midway-PWM Portland

2h 10mnonstop

5:20 am - 10:00 amPWM Portland-MDW Chicago Midway

5h 40m1 stop Baltimore/Washington

$477Southwest

Sat, Oct 3 - Mon, Oct 5

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Southwest flights from Chicago Midway Airport to Maine

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

Southwest

Oct 26

MDW6:40 pmChicago Midway

2h 15m

PWM9:55 pmPortland

Oct 27

PWM6:00 pmPortland

2h 35m

MDW7:35 pmChicago Midway

$353

Southwest

Oct 27

MDW7:45 amChicago Midway

2h 10m

PWM10:55 amPortland

Nov 3

PWM3:25 pmPortland

7h 00m

1 stop

MDW9:25 pmChicago Midway

$363

Southwest

Oct 27

MDW7:45 amChicago Midway

2h 10m

PWM10:55 amPortland

Nov 3

PWM3:25 pmPortland

8h 15m

2 stops

MDW10:40 pmChicago Midway

$368

Delta flights from Chicago Midway Airport to Maine

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

Delta

Dec 9

MDW9:37 amChicago Midway

5h 34m

1 stop

PWM4:11 pmPortland

Jan 7

PWM12:50 pmPortland

6h 47m

1 stop

MDW6:37 pmChicago Midway

$373

Delta

Dec 9

MDW1:41 pmChicago Midway

8h 39m

2 stops

PWM11:20 pmPortland

Jan 6

PWM12:50 pmPortland

6h 47m

1 stop

MDW6:37 pmChicago Midway

$378

Delta

Oct 28

MDW6:04 amChicago Midway

9h 43m

2 stops

PWM4:47 pmPortland

Nov 3

PWM6:03 amPortland

10h 14m

2 stops

MDW3:17 pmChicago Midway

$384

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

Quickest round-trip

ChicagoPortland

MDW Chicago Midway - PWM Portland

MDWPWM

Chicago Midway

Sat 10/24

4:10 pm-7:25 pm

Nonstop2h 15m

Portland

Wed 10/28

6:00 pm-7:35 pm

Nonstop2h 35m

$353

ChicagoPortland

MDW Chicago Midway - PWM Portland

MDWPWM

Chicago Midway

Mon 10/26

6:40 pm-9:55 pm

Nonstop2h 15m

Portland

Wed 10/28

6:00 pm-7:35 pm

Nonstop2h 35m

$353

ChicagoPortland

MDW Chicago Midway - PWM Portland

MDWPWM

Chicago Midway

Mon 10/26

6:40 pm-9:55 pm

Nonstop2h 15m

Portland

Tue 10/27

6:00 pm-7:35 pm

Nonstop2h 35m

$353

ChicagoPortland

MDW Chicago Midway - PWM Portland

MDWPWM

Chicago Midway

Mon 10/26

6:25 pm-11:55 pm

1 stop4h 30m

Portland

Wed 10/28

6:00 pm-7:35 pm

Nonstop2h 35m

$363

ChicagoPortland

MDW Chicago Midway - PWM Portland

MDWPWM

Chicago Midway

Sat 10/24

6:45 am-2:50 pm

1 stop7h 05m

Portland

Wed 10/28

6:00 pm-7:35 pm

Nonstop2h 35m

$363

ChicagoPortland

MDW Chicago Midway - PWM Portland

MDWPWM

Chicago Midway

Tue 10/27

7:45 am-10:55 am

Nonstop2h 10m

Portland

Wed 11/4

12:45 pm-6:55 pm

1 stop7h 10m

$363

ChicagoPortland

MDW Chicago Midway - PWM Portland

MDWPWM

Chicago Midway

Tue 10/27

7:45 am-10:55 am

Nonstop2h 10m

Portland

Tue 11/3

3:25 pm-9:25 pm

1 stop7h 00m

$363

ChicagoPortland

MDW Chicago Midway - PWM Portland

MDWPWM

Chicago Midway

Mon 10/26

6:40 pm-9:55 pm

Nonstop2h 15m

Portland

Tue 10/27

5:40 am-11:20 am

1 stop6h 40m

$363

ChicagoPortland

MDW Chicago Midway - PWM Portland

MDWPWM

Chicago Midway

Sat 10/24

4:10 pm-7:25 pm

Nonstop2h 15m

Portland

Tue 10/27

11:35 am-4:55 pm

1 stop6h 20m

$363

Cheapest one-way

ChicagoPortland

MDW Chicago Midway - PWM Portland

MDWPWM

Chicago Midway

Mon 10/26

6:15 am-4:24 pm

2 stops33h 09m

$157

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 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 Friday. Travelers who choose to depart for Maine on a Friday will often find tickets for as low as $289. Flights from Chicago Midway Airport to Maine on a Saturday will generally be more expensive and average around $405. 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 Airport to Maine flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport 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 39% 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	$157
Fastest flight time	2h 05m
Direct flights	Every day
Airports in Maine	49 airports

The best one-way flight to Maine from Chicago Midway Airport in the past 72 hours is $157. The best round-trip flight deal from Chicago Midway Airport to Maine found on momondo in the last 72 hours is $353.

The fastest flight from Chicago Midway Airport to Maine takes 2h 05m

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).

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 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 Embraer 175 (Enhanced Winglets), representing 15.15% of all bookings. The subsequent popular models are Boeing 737-800 at 15.15%, Embraer 175 at 15.15%, and Boeing 737 MAX 8 at 12.12%.

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.