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

JetBlue, United Airlines, and Delta 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 39% of people opting to fly with this airline when traveling to Portland, Maine. Keep in mind that there are 5 different airlines that fly to Portland, Maine on a routine basis, so you have a few additional options to choose from.

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

As of November 2025, 38 flights take off from Wisconsin and land in Portland, Maine each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.

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 15m on average. If you fly from Green Bay (another popular airport in Wisconsin) to Boston, then the average flight time is 3h 52m.

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 5 operators available for flights from Wisconsin to Portland Airport as of November 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.

$96 Cheap Flights from Wisconsin to Portland in 2025/26

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Find the cheapest flights from Wisconsin to Portland

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:25 pm - 12:20 amORD-PWM

4h 55m1 stop

5:57 pm - 10:05 pmPWM-ORD

5h 08m1 stop

$249Delta

Find Deal

Mon, Mar 2 - Wed, Mar 4

1:35 pm - 10:43 pmORD-PWM

8h 08m2 stops

6:00 am - 1:26 pmPWM-ORD

8h 26m1 stop

$254Delta

Find Deal

Wed, Dec 31 - Tue, Jan 6

3:57 pm - 11:43 pmMSN-PWM

6h 46m1 stop

5:07 pm - 10:40 pmPWM-MSN

6h 33m1 stop

$259American Airlines

Find Deal

Fri, Jan 30 - Mon, Feb 2

4:05 pm - 10:32 pmORD-PWM

5h 27m1 stop

3:55 pm - 10:54 pmPWM-ORD

7h 59m1 stop

$260American Airlines

Find Deal

Sat, Dec 13 - Mon, Dec 15

3:50 pm - 11:20 pmORD-PWM

6h 30m1 stop

4:11 pm - 6:23 pmPWM-ORD

3h 12mnonstop

$289United Airlines

Find Deal

Fri, Feb 27 - Tue, Mar 3

4:10 pm - 11:20 pmORD-PWM

6h 10m1 stop

6:00 am - 1:14 pmPWM-ORD

8h 14m1 stop

$299United Airlines

Find Deal

Fri, Feb 27 - Thu, Mar 5

5:40 am - 10:49 amORD-PWM

28h 09m2 stops

6:18 pm - 12:08 pmPWM-ORD

18h 50m1 stop

$338Multiple Airlines

Find Deal

Sun, Mar 1 - Sat, Mar 7

6:00 pm - 10:49 amORD-PWM

15h 49m2 stops

6:18 pm - 12:51 pmPWM-ORD

19h 33m1 stop

$346Multiple Airlines

Find Deal

Sun, Mar 1 - Wed, Mar 4

5:30 am - 2:55 pmMSP-PWM

8h 25m2 stops

5:30 am - 2:45 pmPWM-MSP

10h 15m2 stops

$349Southwest

Find Deal

Tue, Dec 9 - Tue, Dec 16

6:50 am - 1:45 pmMKE-PWM

5h 55m1 stop

1:10 pm - 7:10 pmPWM-MKE

7h 00m1 stop

$407Southwest

Find Deal

Sun, Mar 1 - Sat, Mar 7

Delta flights from Wisconsin to Portland, Maine

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

Delta

Mar 2

ORD6:25 pmChicago O'Hare Intl

4h 55m

1 stop

PWM12:20 amPortland

Mar 4

PWM5:57 pmPortland

5h 08m

1 stop

ORD10:05 pmChicago O'Hare Intl

$249

Find similar

Delta

Dec 31

ORD1:35 pmChicago O'Hare Intl

8h 08m

2 stops

PWM10:43 pmPortland

Jan 6

PWM6:00 amPortland

8h 26m

1 stop

ORD1:26 pmChicago O'Hare Intl

$254

Find similar

Delta

Dec 31

ORD1:35 pmChicago O'Hare Intl

8h 08m

2 stops

PWM10:43 pmPortland

Jan 6

PWM6:00 amPortland

11h 43m

2 stops

ORD4:43 pmChicago O'Hare Intl

$259

Find similar

American Airlines flights from Wisconsin to Portland, Maine

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

American Airlines

Jan 30

MSN3:57 pmMadison Truax Field

6h 46m

1 stop

PWM11:43 pmPortland

Feb 2

PWM5:07 pmPortland

6h 33m

1 stop

MSN10:40 pmMadison Truax Field

$259

Find similar

American Airlines

Dec 13

ORD4:05 pmChicago O'Hare Intl

5h 27m

1 stop

PWM10:32 pmPortland

Dec 15

PWM3:55 pmPortland

7h 59m

1 stop

ORD10:54 pmChicago O'Hare Intl

$260

Find similar

American Airlines

Nov 21

ORD6:06 amChicago O'Hare Intl

4h 40m

1 stop

PWM11:46 amPortland

Nov 23

PWM6:00 amPortland

5h 27m

1 stop

ORD10:27 amChicago O'Hare Intl

$269

Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 3/2

6:25 pm-12:20 am

1 stop4h 55m

Portland

Wed 3/4

5:57 pm-10:05 pm

1 stop5h 08m

$249

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 12/31

1:35 pm-10:43 pm

2 stops8h 08m

Portland

Tue 1/6

6:00 am-1:26 pm

1 stop8h 26m

$254

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Fri 1/30

3:57 pm-11:43 pm

1 stop6h 46m

Portland

Mon 2/2

5:07 pm-10:40 pm

1 stop6h 33m

$259

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 12/13

4:05 pm-10:32 pm

1 stop5h 27m

Portland

Mon 12/15

3:55 pm-10:54 pm

1 stop7h 59m

$260

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 2/27

3:50 pm-11:20 pm

1 stop6h 30m

Portland

Tue 3/3

4:11 pm-6:23 pm

Nonstop3h 12m

$289

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 2/27

4:10 pm-11:20 pm

1 stop6h 10m

Portland

Thu 3/5

6:00 am-1:14 pm

1 stop8h 14m

$299

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 3/1

5:40 am-10:49 am

2 stops28h 09m

Portland

Sat 3/7

6:18 pm-12:08 pm

1 stop18h 50m

$338

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 3/1

6:00 pm-10:49 am

2 stops15h 49m

Portland

Wed 3/4

6:18 pm-12:51 pm

1 stop19h 33m

$346

MinneapolisPortland

MSP - PWM

MSPPWM

Minneapolis St Paul

Tue 12/9

5:30 am-2:55 pm

2 stops8h 25m

Portland

Tue 12/16

5:30 am-2:45 pm

2 stops10h 15m

$349

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sun 3/1

6:50 am-1:45 pm

1 stop5h 55m

Portland

Sat 3/7

1:10 pm-7:10 pm

1 stop7h 00m

$407

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 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 $388 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 59% 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

Fastest flight time	2h 19m
Direct flights	Every day
Airports in Portland, Maine	1 airport

The fastest flight from Wisconsin to Portland, Maine takes 2h 19m

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 5 operators available for flights from Wisconsin to Portland Airport as of November 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
American Airlines	PriceFrom $238	Free Cancellation	Rating 7.2 11,047 reviews	Search American Airlines flights
Southwest	PriceFrom $246	Free Cancellation	Rating 8.0 4,238 reviews	Search Southwest flights
Delta	PriceFrom $251	Free Cancellation	Rating 7.9 8,004 reviews	Search Delta flights
United Airlines	PriceFrom $267	Free Cancellation	Rating 7.4 9,012 reviews	Search United Airlines 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 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 $96

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 5/7. 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

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Find the cheapest flights from Wisconsin to Portland

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Delta flights from Wisconsin to Portland, Maine

Our best Delta 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.

See travel insights to Portland from

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 59% 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?

JetBlue, United Airlines, and Delta 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 November 2025, 38 flights take off from Wisconsin and land in Portland, Maine each week. The most common flight departure day for this route is Mon, with 16% 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

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