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

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

Which airline has the best punctuality record on Chicago to Portland flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.

What day of the week experiences the fewest flight delays on this route?

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

What is the most punctual flight time for Chicago to Portland flights?

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.

How often are flights from Chicago to Portland delayed?

Historically, on average around 9% of flights between Chicago and Portland have experienced a delay on any given week. The average delay length over the past 12 months has been 99 minutes.

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

Prices for flights from Chicago Midway Airport to Portland Airport are refreshed on a daily basis.

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

As of November 2025, there is 1 operator available to choose from for flights from Chicago Midway Airport to Portland Airport.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Portland Airport.

What documentation or ID do you need to fly to Portland Airport?

The necessary travel and health documents for your Portland 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.

$111 Cheap Flights from Chicago Midway Airport to Portland, Maine in 2025/26

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Find the cheapest flights from Chicago Midway Airport to Portland

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

9:34 am - 4:07 pmMDW-PWM

5h 33m1 stop

6:08 am - 11:55 amPWM-MDW

6h 47m1 stop

$279Delta

Find Deal

Mon, Dec 8 - Mon, Dec 15

3:29 pm - 10:43 pmMDW-PWM

6h 14m1 stop

6:00 am - 4:31 pmPWM-MDW

11h 31m2 stops

$284Delta

Find Deal

Thu, Jan 1 - Tue, Jan 6

6:50 am - 3:15 pmMDW-PWM

7h 25m1 stop

5:30 pm - 11:35 pmPWM-MDW

7h 05m1 stop

$294Southwest

Find Deal

Mon, Mar 2 - Fri, Mar 6

5:15 pm - 12:20 amMDW-PWM

6h 05m1 stop

12:35 pm - 4:55 pmPWM-MDW

5h 20m1 stop

$296Southwest

Find Deal

Mon, Jan 5 - Sat, Jan 10

1:35 pm - 10:45 pmMDW-PWM

8h 10m2 stops

5:30 pm - 11:35 pmPWM-MDW

7h 05m1 stop

$299Southwest

Find Deal

Mon, Mar 2 - Fri, Mar 6

9:29 am - 4:08 pmMDW-PWM

5h 39m1 stop

5:30 am - 10:34 amPWM-MDW

6h 04m1 stop

$314Delta

Find Deal

Tue, Dec 30 - Wed, Jan 7

9:29 am - 4:08 pmMDW-PWM

5h 39m1 stop

6:00 am - 12:48 pmPWM-MDW

7h 48m2 stops

$319Delta

Find Deal

Tue, Dec 30 - Wed, Jan 7

9:20 am - 2:55 pmMDW-PWM

4h 35m1 stop

5:45 am - 11:35 amPWM-MDW

6h 50m1 stop

$324Southwest

Find Deal

Thu, Jan 1 - Tue, Jan 6

4:13 pm - 11:04 pmMDW-PWM

5h 51m1 stop

12:15 pm - 5:37 pmPWM-MDW

6h 22m1 stop

$325Delta

Find Deal

Sat, Feb 28 - Tue, Mar 3

2:30 pm - 10:15 pmMDW-PWM

6h 45m2 stops

3:30 pm - 9:05 pmPWM-MDW

6h 35m1 stop

$329Southwest

Find Deal

Wed, Dec 17 - Wed, Dec 24

Delta flights from Chicago Midway Airport to Portland, Maine

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

Delta

Dec 8

MDW9:34 amChicago Midway

5h 33m

1 stop

PWM4:07 pmPortland

Dec 15

PWM6:08 amPortland

6h 47m

1 stop

MDW11:55 amChicago Midway

$279

Find similar

Delta

Jan 1

MDW3:29 pmChicago Midway

6h 14m

1 stop

PWM10:43 pmPortland

Jan 7

PWM6:00 amPortland

7h 48m

2 stops

MDW12:48 pmChicago Midway

$284

Find similar

Delta

Dec 30

MDW9:29 amChicago Midway

5h 39m

1 stop

PWM4:08 pmPortland

Jan 7

PWM5:30 amPortland

6h 04m

1 stop

MDW10:34 amChicago Midway

$314

Find similar

Southwest flights from Chicago Midway Airport to Portland, Maine

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

Southwest

Mar 2

MDW6:50 amChicago Midway

7h 25m

1 stop

PWM3:15 pmPortland

Mar 6

PWM5:30 pmPortland

7h 05m

1 stop

MDW11:35 pmChicago Midway

$294

Find similar

Southwest

Jan 5

MDW5:15 pmChicago Midway

6h 05m

1 stop

PWM12:20 amPortland

Jan 10

PWM12:35 pmPortland

5h 20m

1 stop

MDW4:55 pmChicago Midway

$296

Find similar

Southwest

Mar 2

MDW1:35 pmChicago Midway

8h 10m

2 stops

PWM10:45 pmPortland

Mar 6

PWM5:30 pmPortland

7h 05m

1 stop

MDW11:35 pmChicago Midway

$299

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Portland, Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 12/8

9:34 am-4:07 pm

1 stop5h 33m

Portland

Mon 12/15

6:08 am-11:55 am

1 stop6h 47m

$279

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 1/1

3:29 pm-10:43 pm

1 stop6h 14m

Portland

Tue 1/6

6:00 am-4:31 pm

2 stops11h 31m

$284

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 3/2

6:50 am-3:15 pm

1 stop7h 25m

Portland

Fri 3/6

5:30 pm-11:35 pm

1 stop7h 05m

$294

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 1/5

5:15 pm-12:20 am

1 stop6h 05m

Portland

Sat 1/10

12:35 pm-4:55 pm

1 stop5h 20m

$296

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 3/2

1:35 pm-10:45 pm

2 stops8h 10m

Portland

Fri 3/6

5:30 pm-11:35 pm

1 stop7h 05m

$299

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 12/30

9:29 am-4:08 pm

1 stop5h 39m

Portland

Wed 1/7

5:30 am-10:34 am

1 stop6h 04m

$314

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 12/30

9:29 am-4:08 pm

1 stop5h 39m

Portland

Wed 1/7

6:00 am-12:48 pm

2 stops7h 48m

$319

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 1/1

9:20 am-2:55 pm

1 stop4h 35m

Portland

Tue 1/6

5:45 am-11:35 am

1 stop6h 50m

$324

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sat 2/28

4:13 pm-11:04 pm

1 stop5h 51m

Portland

Tue 3/3

12:15 pm-5:37 pm

1 stop6h 22m

$325

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 12/17

2:30 pm-10:15 pm

2 stops6h 45m

Portland

Wed 12/24

3:30 pm-9:05 pm

1 stop6h 35m

$329

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 Portland, 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

Delays

Other information

What is the cheapest day to depart on your flight to Portland, Maine?

On average, the least expensive day to fly to Portland, Maine from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $337. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Thursday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $397.

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

In the evening is the cheapest time of day to fly from Chicago Midway Airport to Portland, Maine when you can find flight prices for as low as $320. Flying to Portland, Maine in the evening is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the afternoon because they tend to be around $376. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago Midway to Portland flight route?

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

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

There is only 1 cabin class available to choose from on Chicago Midway to Portland 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 Portland, Maine flights?

You could potentially save up to 74% on your flight if you consider stops on a Chicago Midway Airport to Portland, Maine flight.

When to book flights from Chicago Midway Airport to Portland, Maine

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Portland, Maine according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to Portland, Maine (MDW to PWM) flight deals and tips

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

Direct flights	None

There are no direct flights from Chicago Midway Airport to Portland, Maine. There are no popular flight routes from Chicago Midway Airport to Portland, Maine.

Search flight deals

How far is Chicago Midway to Portland by plane?
The straight-line distance from Chicago Midway to Portland is 894.8 mi. By plane, this route typically takes 4h 35m.
When did momondo last update prices for flights from Chicago Midway Airport to Portland Airport?
Prices for flights from Chicago Midway Airport to Portland Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Portland Airport?
As of November 2025, there is 1 operator available to choose from for flights from Chicago Midway Airport to Portland Airport.
How old do you have to be to fly from Chicago Midway Airport to Portland Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Portland Airport.
What documentation or ID do you need to fly to Portland Airport?
The necessary travel and health documents for your Portland 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 Chicago Midway Airport to Portland, Maine?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Portland, Maine is Boeing 737-800 (18.92% of total bookings). The next most popular plane models are Embraer 175 (13.51%), Embraer 175 (Enhanced Winglets) (10.81%), and Boeing 737-800 Passenger/BBJ2 (winglets) (10.81%).
What is the most popular airline from Chicago Midway Airport to Portland, Maine?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to Portland, Maine is Southwest, representing 100% of all bookings.

Best airlines flying from Chicago Midway Airport to Portland, Maine

Compare and see reviews for airlines that fly from Chicago Midway Airport to Portland, Maine with momondo

Airline	Rating	Free Cancellation	Price
Southwest	PriceFrom $313	Free Cancellation	Rating 8.0 4,235 reviews		Search Southwest flights

North Conway

Boothbay Harbor

Jackson

Conway

Lewiston

Freeport

Brunswick

Bartlett

Auburn

Gorham

Windham

Intervale

Oxford

Bath

Georgetown

Falmouth

Tamworth

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Portland. momondo saves you time and could save you money on your trip.

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

momondo does allow users to show only those flights to Portland from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Portland from Chicago.

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

Of course. momondo tracks the price of Chicago to Portland flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Cheap flights from Chicago Midway Airport to Portland from $111

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Big names and deals

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Find the cheapest flights from Chicago Midway Airport to Portland

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Delta flights from Chicago Midway Airport to Portland, Maine

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

Southwest flights from Chicago Midway Airport to Portland, Maine

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

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Use the filters below to find and compare flights from Chicago Midway Airport to Portland, Maine that are best for you.

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

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

What is the cheapest Chicago Midway to Portland flight route?

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

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

There is only 1 cabin class available to choose from on Chicago Midway to Portland 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 Portland, Maine flights?

You could potentially save up to 74% on your flight if you consider stops on a Chicago Midway Airport to Portland, Maine flight.

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

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

How often are flights from Chicago to Portland delayed?

Historically, on average around 9% of flights between Chicago and Portland have experienced a delay on any given week. The average delay length over the past 12 months has been 99 minutes.

What is the most punctual flight time for Chicago to Portland flights?

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to Portland flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.

When to book flights from Chicago Midway Airport to Portland, Maine

Cheap Chicago Midway Airport to Portland, Maine (MDW to PWM) flight deals and tips

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

Direct flights

How far is Chicago Midway to Portland by plane?

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

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

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

What documentation or ID do you need to fly to Portland Airport?

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

What is the most popular airline from Chicago Midway Airport to Portland, Maine?

Best airlines flying from Chicago Midway Airport to Portland, Maine

Compare and see reviews for airlines that fly from Chicago Midway Airport to Portland, Maine with momondo

Traveling to a place near Portland?

Why use momondo?

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

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

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

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

An easier way to manage your Portland, 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing Maine