What is the cheapest airline that flies from Wisconsin to Portland?

Sun Country Air, American Airlines, and JetBlue are the most popular carriers operating from Wisconsin to Portland

What airlines fly to Portland, Maine?

American Airlines, Delta and JetBlue are the top three most popular airlines that fly to Portland, Maine from Wisconsin according to our data. American Airlines is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Portland, Maine. Keep in mind that there are 6 different airlines that fly to Portland, Maine on a routine basis, so you have a few additional options to choose from.

How long does it take to fly to Portland, Maine?

The flight from Wisconsin to Portland, Maine depends on which airports you’re departing and arriving from and whether or not you have a layover. If you fly from Milwaukee (a popular airport in Wisconsin) to Boston (the most popular airport in Portland, Maine), then the flight time is 2h 12m on average. If you fly from Green Bay (another popular airport in Wisconsin) to Boston, then the average flight time is 4h 33m.

How many flights depart from Wisconsin to Portland, Maine on average per week?

As of July 2025, 54 flights take off from Wisconsin and land in Portland, Maine each week. The most common flight departure day for this route is Thu, with 22% of weekly flights taking off on this day.

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

Prices for flights from Wisconsin to Portland Airport were last updated today.

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

There are 6 operators available for flights from Wisconsin to Portland Airport as of July 2025.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Wisconsin 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.

$78 Cheap Flights from Wisconsin to Portland in 2025

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Find the cheapest flights from Wisconsin to Portland

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

8:00 am - 11:44 amMSP-PWM

2h 44mnonstop

12:54 pm - 3:00 pmPWM-MSP

3h 06mnonstop

$155Sun Country Air

Find Deal

Sun, Aug 24 - Thu, Aug 28

7:00 am - 10:46 amMSP-PWM

2h 46mnonstop

12:54 pm - 3:00 pmPWM-MSP

3h 06mnonstop

$158Sun Country Air

Find Deal

Thu, Aug 21 - Thu, Aug 28

6:10 am - 1:22 pmORD-PWM

6h 12m1 stop

7:30 am - 12:10 pmPWM-ORD

5h 40m1 stop

$183JetBlue

Find Deal

Wed, Sep 3 - Tue, Sep 9

1:35 pm - 10:07 pmORD-PWM

7h 32m1 stop

7:09 am - 12:21 pmPWM-ORD

6h 12m1 stop

$185JetBlue

Find Deal

Fri, Sep 26 - Mon, Sep 29

6:25 pm - 9:59 pmORD-PWM

2h 34mnonstop

5:02 pm - 6:53 pmPWM-ORD

2h 51mnonstop

$208United Airlines

Find Deal

Sat, Aug 23 - Sat, Aug 30

10:05 am - 1:42 pmORD-PWM

2h 37mnonstop

6:01 am - 7:57 amPWM-ORD

2h 56mnonstop

$217American Airlines

Find Deal

Wed, Sep 3 - Tue, Sep 9

3:32 pm - 9:45 pmORD-PWM

5h 13m1 stop

6:30 am - 8:32 amPWM-ORD

3h 02mnonstop

$225American Airlines

Find Deal

Sat, Aug 23 - Sat, Aug 30

7:15 am - 1:22 pmORD-PWM

5h 07m1 stop

6:23 pm - 8:23 pmPWM-ORD

3h 00mnonstop

$227United Airlines

Find Deal

Tue, Sep 9 - Sat, Sep 13

5:45 am - 12:29 pmORD-PWM

5h 44m1 stop

6:31 am - 12:40 pmPWM-ORD

7h 09m1 stop

$228Delta

Find Deal

Sun, Aug 31 - Wed, Sep 3

2:25 pm - 12:03 amORD-PWM

8h 38m2 stops

5:30 pm - 11:56 pmPWM-ORD

7h 26m1 stop

$233Delta

Find Deal

Sat, Aug 23 - Sat, Aug 30

JetBlue flights from Wisconsin to Portland, Maine

Our best JetBlue deals on Wisconsin to Portland, Maine flight tickets

JetBlue

Sep 3

ORD6:10 amChicago O'Hare Intl

6h 12m

1 stop

PWM1:22 pmPortland

Sep 9

PWM7:30 amPortland

5h 40m

1 stop

ORD12:10 pmChicago O'Hare Intl

$183

Find similar

JetBlue

Sep 26

ORD1:35 pmChicago O'Hare Intl

7h 32m

1 stop

PWM10:07 pmPortland

Sep 29

PWM7:09 amPortland

6h 12m

1 stop

ORD12:21 pmChicago O'Hare Intl

$185

Find similar

JetBlue

Oct 1

ORD1:35 pmChicago O'Hare Intl

7h 31m

1 stop

PWM10:06 pmPortland

Oct 7

PWM7:30 amPortland

5h 40m

1 stop

ORD12:10 pmChicago O'Hare Intl

$193

Find similar

American Airlines flights from Wisconsin to Portland, Maine

Our best American Airlines deals on Wisconsin to Portland, Maine flight tickets

American Airlines

Sep 3

ORD10:05 amChicago O'Hare Intl

2h 37m

PWM1:42 pmPortland

Sep 9

PWM6:01 amPortland

2h 56m

ORD7:57 amChicago O'Hare Intl

$217

Find similar

American Airlines

Aug 23

ORD3:32 pmChicago O'Hare Intl

5h 13m

1 stop

PWM9:45 pmPortland

Aug 30

PWM6:30 amPortland

3h 02m

ORD8:32 amChicago O'Hare Intl

$225

Find similar

American Airlines

Sep 3

ORD9:55 amChicago O'Hare Intl

7h 16m

1 stop

PWM6:11 pmPortland

Sep 9

PWM6:01 amPortland

2h 56m

ORD7:57 amChicago O'Hare Intl

$234

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MinneapolisPortland

MSP - PWM

MSPPWM

Minneapolis St Paul

Sun 8/24

8:00 am-11:44 am

Nonstop2h 44m

Portland

Thu 8/28

12:54 pm-3:00 pm

Nonstop3h 06m

$155

MinneapolisPortland

MSP - PWM

MSPPWM

Minneapolis St Paul

Thu 8/21

7:00 am-10:46 am

Nonstop2h 46m

Portland

Thu 8/28

12:54 pm-3:00 pm

Nonstop3h 06m

$158

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 9/3

6:10 am-1:22 pm

1 stop6h 12m

Portland

Tue 9/9

7:30 am-12:10 pm

1 stop5h 40m

$183

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 9/26

1:35 pm-10:07 pm

1 stop7h 32m

Portland

Mon 9/29

7:09 am-12:21 pm

1 stop6h 12m

$185

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 8/23

6:25 pm-9:59 pm

Nonstop2h 34m

Portland

Sat 8/30

5:02 pm-6:53 pm

Nonstop2h 51m

$208

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 9/3

10:05 am-1:42 pm

Nonstop2h 37m

Portland

Tue 9/9

6:01 am-7:57 am

Nonstop2h 56m

$217

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 8/23

3:32 pm-9:45 pm

1 stop5h 13m

Portland

Sat 8/30

6:30 am-8:32 am

Nonstop3h 02m

$225

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 9/9

7:15 am-1:22 pm

1 stop5h 07m

Portland

Sat 9/13

6:23 pm-8:23 pm

Nonstop3h 00m

$227

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 8/31

5:45 am-12:29 pm

1 stop5h 44m

Portland

Wed 9/3

6:31 am-12:40 pm

1 stop7h 09m

$228

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 8/23

2:25 pm-12:03 am

2 stops8h 38m

Portland

Sat 8/30

5:30 pm-11:56 pm

1 stop7h 26m

$233

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How to get the cheapest flight ticket from Wisconsin 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

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 Wisconsin is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $361. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Monday is the most expensive day to depart from Wisconsin because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $472.

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

In the afternoon is the cheapest time of day to fly from Wisconsin to Portland, Maine when you can find flight prices for as low as $376. Flying to Portland, Maine in the afternoon is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the morning because they tend to be around $426. Of course, these prices can vary depending on the time of year and what airport you fly to.

How far in advance should I book a flight to Portland, Maine?

You are more likely to see cheaper flights to Portland, Maine from Wisconsin when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland, Maine for around $379 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland, Maine from Wisconsin for as low as $228 on momondo.

Can stopping save me money on Wisconsin to Portland, Maine flights?

You could potentially save up to 72% on your flight if you consider stops on a Wisconsin to Portland, Maine flight.

Cheap Wisconsin to Portland, Maine flight deals and tips

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

Best Price Found	$78
Fastest flight time	2h 17m
Direct flights	Every day
Airports in Portland, Maine	1 airport

The best one-way flight to Portland, Maine from Wisconsin in the past 72 hours is $78. The best round-trip flight deal from Wisconsin to Portland, Maine found on momondo in the last 72 hours is $155.

The fastest flight from Wisconsin to Portland, Maine takes 2h 17m

Direct flights go from Wisconsin to Portland, Maine every day.

There is 1 airport near Portland, Maine: Portland (PWM)

Search flight deals

When did momondo last update prices for flights from Wisconsin to Portland Airport?
Prices for flights from Wisconsin to Portland Airport were last updated today.
How many operators does momondo search for flights from Wisconsin to Portland Airport?
There are 6 operators available for flights from Wisconsin to Portland Airport as of July 2025.
How old do you have to be to fly from Wisconsin to Portland Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Wisconsin 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.

Best airlines flying from Wisconsin to Portland, Maine

Compare and see reviews for airlines that fly from Wisconsin to Portland, Maine with momondo

Airline	Rating	Free Cancellation	Price
Southwest	PriceFrom $246	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
Delta	PriceFrom $248	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
American Airlines	PriceFrom $258	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $267	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights

North Conway

Boothbay Harbor

Jackson

Conway

Freeport

Bartlett

Lewiston

Gorham

Brunswick

Auburn

Intervale

Windham

Falmouth

Bath

Georgetown

Oxford

Tamworth

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Portland from Wisconsin.

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

Yes. momondo allows you to filter the results for Wisconsin to Portland flights to just show those with flexible booking policies.

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

Once all potential Wisconsin to Portland flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

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

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.

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Cheap flights from Wisconsin to Portland from $78

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wisconsin to Portland departing on 8/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Wisconsin to Portland

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JetBlue flights from Wisconsin to Portland, Maine

Our best JetBlue deals on Wisconsin to Portland, Maine flight tickets

American Airlines flights from Wisconsin to Portland, Maine

Our best American Airlines deals on Wisconsin to Portland, Maine flight tickets

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

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How to get the cheapest flight ticket from Wisconsin 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?

How far in advance should I book a flight to Portland, Maine?

Can stopping save me money on Wisconsin to Portland, Maine flights?

You could potentially save up to 72% on your flight if you consider stops on a Wisconsin to Portland, Maine flight.

What is the cheapest airline that flies from Wisconsin to Portland?

Sun Country Air, American Airlines, and JetBlue are the most popular carriers operating from Wisconsin to Portland

What airlines fly to Portland, Maine?

How many flights depart from Wisconsin to Portland, Maine on average per week?

As of July 2025, 54 flights take off from Wisconsin and land in Portland, Maine each week. The most common flight departure day for this route is Thu, with 22% of weekly flights taking off on this day.

How long does it take to fly to Portland, Maine?

Cheap Wisconsin to Portland, Maine flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Portland, Maine

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

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

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

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

Best airlines flying from Wisconsin to Portland, Maine

Compare and see reviews for airlines that fly from Wisconsin 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 Wisconsin to Portland?

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

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

I’m not ready to book a flight from Wisconsin 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