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

United Airlines, Delta, and Breeze Airways 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 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 19m on average. If you fly from Madison (another popular airport in Wisconsin) to Boston, then the average flight time is 2h 25m.

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 4 operators available for flights from Wisconsin to Portland Airport as of October 2026.

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.

$152 Cheap Flights from Wisconsin to Portland, Maine in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Wisconsin to Portland

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:10 am - 3:16 pmMKE Milwaukee-Mitchell-PWM Portland

6h 06m1 stop New York John F Kennedy Intl

4:50 pm - 8:15 pmPWM Portland-MKE Milwaukee-Mitchell

4h 25m1 stop Detroit Metropolitan Wayne County

$293Delta

Wed, Nov 11 - Mon, Nov 16

5:20 am - 3:16 pmMKE Milwaukee-Mitchell-PWM Portland

8h 56m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl

4:50 pm - 8:15 pmPWM Portland-MKE Milwaukee-Mitchell

4h 25m1 stop Detroit Metropolitan Wayne County

$298Delta

Wed, Nov 11 - Mon, Nov 16

3:14 pm - 9:52 pmGRB Green Bay Austin-Straubel-PWM Portland

5h 38m1 stop Chicago O'Hare Intl

5:08 pm - 10:38 pmPWM Portland-GRB Green Bay Austin-Straubel

6h 30m1 stop Chicago O'Hare Intl

$339United Airlines

Fri, Nov 13 - Sun, Nov 15

8:15 am - 3:38 pmMSN Madison Truax Field-PWM Portland

6h 23m1 stop Chicago O'Hare Intl

4:47 pm - 10:23 pmPWM Portland-MSN Madison Truax Field

6h 36m1 stop Chicago O'Hare Intl

$341United Airlines

Sat, Dec 5 - Tue, Dec 8

1:55 pm - 10:46 pmMSN Madison Truax Field-PWM Portland

7h 51m1 stop Washington, D.C. Reagan-National

4:02 pm - 10:35 pmPWM Portland-MSN Madison Truax Field

7h 33m1 stop Washington, D.C. Reagan-National

$341American Airlines

Sat, Dec 5 - Tue, Dec 8

5:00 am - 2:35 pmMSN Madison Truax Field-PWM Portland

8h 35m2 stops Chicago O'Hare Intl Washington, D.C. Reagan-National

4:02 pm - 10:34 pmPWM Portland-MSN Madison Truax Field

7h 32m1 stop Washington, D.C. Reagan-National

$346American Airlines

Sat, Dec 5 - Tue, Dec 8

4:35 pm - 9:50 pmMKE Milwaukee-Mitchell-PWM Portland

4h 15m1 stop Baltimore/Washington

5:15 am - 11:00 amPWM Portland-MKE Milwaukee-Mitchell

6h 45m2 stops Baltimore/Washington Chicago Midway

$429Southwest

Tue, Dec 1 - Mon, Dec 7

6:20 am - 12:25 pmMKE Milwaukee-Mitchell-PWM Portland

5h 05m1 stop Baltimore/Washington

5:10 pm - 11:05 pmPWM Portland-MKE Milwaukee-Mitchell

6h 55m2 stops Baltimore/Washington Lambert-St Louis

$542Southwest

Fri, Oct 30 - Mon, Nov 2

4:58 pm - 3:25 pmMSN Madison Truax Field-PWM Portland

21h 27m3 stops Fort Myers SW Florida Intl Greenville Pittsburgh

5:09 pm - 4:18 pmPWM Portland-MSN Madison Truax Field

24h 09m2 stops Raleigh-Durham Fort Myers SW Florida Intl

$844Breeze Airways

Sat, Oct 31 - Tue, Nov 3

2:36 pm - 9:08 amATW Appleton Intl-PWM Portland

41h 32m2 stops Phoenix-Mesa Gateway Orlando

9:48 am - 10:53 pmPWM Portland-ATW Appleton Intl

14h 05m1 stop Orlando

$928Multiple Airlines

Sat, Dec 19 - Wed, Dec 30

Cheap last minute flights

Enter your travel dates to find the best prices.

2:36 pm - 9:46 pmATW Appleton Intl-PWM Portland

6h 10m1 stop Chicago O'Hare Intl

5:08 pm - 11:17 pmPWM Portland-ATW Appleton Intl

7h 09m1 stop Chicago O'Hare Intl

$377United Airlines

Sat, Oct 24 - Mon, Oct 26

2:36 pm - 11:28 pmATW Appleton Intl-PWM Portland

7h 52m2 stops Chicago O'Hare Intl Newark

5:08 pm - 11:17 pmPWM Portland-ATW Appleton Intl

7h 09m1 stop Chicago O'Hare Intl

$382United Airlines

Sat, Oct 24 - Mon, Oct 26

2:36 pm - 11:28 pmATW Appleton Intl-PWM Portland

7h 52m2 stops Chicago O'Hare Intl Newark

3:41 pm - 11:17 pmPWM Portland-ATW Appleton Intl

8h 36m2 stops Newark Chicago O'Hare Intl

$387United Airlines

Sat, Oct 24 - Mon, Oct 26

7:00 am - 12:22 pmMSN Madison Truax Field-PWM Portland

4h 22m1 stop Detroit Metropolitan Wayne County

6:28 am - 10:45 amPWM Portland-MSN Madison Truax Field

5h 17m1 stop New York LaGuardia

$468Delta

Sat, Oct 24 - Sun, Oct 25

10:53 am - 9:00 pmMSN Madison Truax Field-PWM Portland

9h 07m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

6:28 am - 10:45 amPWM Portland-MSN Madison Truax Field

5h 17m1 stop New York LaGuardia

$473Delta

Sat, Oct 24 - Sun, Oct 25

2:58 pm - 11:43 pmMKE Milwaukee-Mitchell-PWM Portland

7h 45m1 stop Chicago O'Hare Intl

6:00 am - 10:14 amPWM Portland-MKE Milwaukee-Mitchell

5h 14m1 stop Charlotte Douglas

$675American Airlines

Sat, Oct 24 - Sun, Oct 25

11:45 am - 10:15 pmMKE Milwaukee-Mitchell-PWM Portland

9h 30m2 stops Orlando Baltimore/Washington

5:40 am - 10:25 amPWM Portland-MKE Milwaukee-Mitchell

5h 45m1 stop Baltimore/Washington

$680Southwest

Sat, Oct 24 - Sun, Oct 25

11:30 am - 5:04 pmCWA Wausau Central Wisconsin-PWM Portland

4h 34m1 stop Chicago O'Hare Intl

5:15 am - 4:21 pmPWM Portland-CWA Wausau Central Wisconsin

12h 06m2 stops Washington, D.C. Reagan-National Chicago O'Hare Intl

$720American Airlines

Tue, Oct 27 - Sun, Nov 1

6:00 am - 2:50 pmMKE Milwaukee-Mitchell-PWM Portland

7h 50m2 stops Chicago Midway Nashville Intl

3:15 pm - 11:55 pmPWM Portland-MKE Milwaukee-Mitchell

9h 40m2 stops Baltimore/Washington Orlando

$726Southwest

Sat, Oct 24 - Sun, Oct 25

6:24 am - 4:57 pmCWA Wausau Central Wisconsin-PWM Portland

9h 33m2 stops Chicago O'Hare Intl New York LaGuardia

5:15 am - 4:21 pmPWM Portland-CWA Wausau Central Wisconsin

12h 06m2 stops Washington, D.C. Reagan-National Chicago O'Hare Intl

$726American Airlines

Tue, Oct 27 - Sun, Nov 1

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United Airlines flights from Wisconsin to Portland, Maine

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

United Airlines

Nov 13

GRB3:14 pmGreen Bay Austin-Straubel

5h 38m

1 stop

PWM9:52 pmPortland

Nov 15

PWM5:08 pmPortland

6h 30m

1 stop

GRB10:38 pmGreen Bay Austin-Straubel

$339

United Airlines

Dec 5

MSN8:15 amMadison Truax Field

6h 23m

1 stop

PWM3:38 pmPortland

Dec 8

PWM4:47 pmPortland

6h 36m

1 stop

MSN10:23 pmMadison Truax Field

$341

United Airlines

Nov 13

GRB1:32 pmGreen Bay Austin-Straubel

8h 49m

2 stops

PWM11:21 pmPortland

Nov 15

PWM5:08 pmPortland

6h 30m

1 stop

GRB10:38 pmGreen Bay Austin-Straubel

$344

American Airlines flights from Wisconsin to Portland, Maine

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

American Airlines

Dec 2

MSN3:12 pmMadison Truax Field

7h 19m

2 stops

PWM11:31 pmPortland

Dec 6

PWM5:00 amPortland

7h 50m

1 stop

MSN11:50 amMadison Truax Field

$350

American Airlines

Dec 5

MSN5:00 amMadison Truax Field

8h 35m

2 stops

PWM2:35 pmPortland

Dec 8

PWM5:00 amPortland

10h 42m

2 stops

MSN2:42 pmMadison Truax Field

$351

American Airlines

Dec 2

MSN3:12 pmMadison Truax Field

7h 19m

2 stops

PWM11:31 pmPortland

Dec 6

PWM5:00 amPortland

10h 42m

2 stops

MSN2:42 pmMadison Truax Field

$355

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

Cheapest round-trip

Quickest round-trip

MilwaukeePortland

MKE Milwaukee-Mitchell - PWM Portland

MKEPWM

Milwaukee-Mitchell

Wed 11/11

8:10 am-3:16 pm

1 stop6h 06m

Portland

Mon 11/16

4:50 pm-8:15 pm

1 stop4h 25m

$293

MilwaukeePortland

MKE Milwaukee-Mitchell - PWM Portland

MKEPWM

Milwaukee-Mitchell

Wed 11/11

5:20 am-3:16 pm

2 stops8h 56m

Portland

Mon 11/16

4:50 pm-8:15 pm

1 stop4h 25m

$298

Green BayPortland

GRB Green Bay Austin-Straubel - PWM Portland

GRBPWM

Green Bay Austin-Straubel

Fri 11/13

3:14 pm-9:52 pm

1 stop5h 38m

Portland

Sun 11/15

5:08 pm-10:38 pm

1 stop6h 30m

$339

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Sat 12/5

8:15 am-3:38 pm

1 stop6h 23m

Portland

Tue 12/8

4:47 pm-10:23 pm

1 stop6h 36m

$341

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Sat 12/5

1:55 pm-10:46 pm

1 stop7h 51m

Portland

Tue 12/8

4:02 pm-10:35 pm

1 stop7h 33m

$341

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Sat 12/5

5:00 am-2:35 pm

2 stops8h 35m

Portland

Tue 12/8

4:02 pm-10:34 pm

1 stop7h 32m

$346

MilwaukeePortland

MKE Milwaukee-Mitchell - PWM Portland

MKEPWM

Milwaukee-Mitchell

Tue 12/1

4:35 pm-9:50 pm

1 stop4h 15m

Portland

Mon 12/7

5:15 am-11:00 am

2 stops6h 45m

$429

MilwaukeePortland

MKE Milwaukee-Mitchell - PWM Portland

MKEPWM

Milwaukee-Mitchell

Fri 10/30

6:20 am-12:25 pm

1 stop5h 05m

Portland

Mon 11/2

5:10 pm-11:05 pm

2 stops6h 55m

$542

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Sat 10/31

4:58 pm-3:25 pm

3 stops21h 27m

Portland

Tue 11/3

5:09 pm-4:18 pm

2 stops24h 09m

$844

AppletonPortland

ATW Appleton Intl - PWM Portland

ATWPWM

Appleton Intl

Sat 12/19

2:36 pm-9:08 am

2 stops41h 32m

Portland

Wed 12/30

9:48 am-10:53 pm

1 stop14h 05m

$928

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 month to fly to Portland, Maine?

The cheapest month to fly to Portland, Maine from Wisconsin is in January. Flight prices, which tend to average around $340, are often lower during this time because this is during the off-season. If you aren’t able to travel to Portland, Maine during the month of January, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $388.

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	$152
Fastest flight time	2h 17m
Direct flights	None

The best one-way flight to Portland, Maine from Wisconsin in the past 72 hours is $152. The best round-trip flight deal from Wisconsin to Portland, Maine found on momondo in the last 72 hours is $293.

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

There are no direct flights from Wisconsin to Portland, Maine. There are no popular flight routes from Wisconsin to Portland, Maine.

Search flight deals

Frequently asked questions about flying from Wisconsin to Portland, Maine

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 4 operators available for flights from Wisconsin to Portland Airport as of October 2026.
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
Delta	PriceFrom $256	Free Cancellation	Rating 7.8 8,650 reviews	Search Delta flights
United Airlines	PriceFrom $276	Free Cancellation	Rating 7.3 10,388 reviews	Search United Airlines flights
American Airlines	PriceFrom $290	Free Cancellation	Rating 7.0 12,181 reviews	Search American Airlines flights
Southwest	PriceFrom $386	Free Cancellation	Rating 7.9 4,211 reviews	Search Southwest flights

North Conway

Jackson

Boothbay Harbor

Brunswick

Lewiston

Freeport

Conway

Auburn

Gorham

Bartlett

Bath

Windham

Intervale

Georgetown

Oxford

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.

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Cheap flights from Wisconsin to Portland from $152

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 12/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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United Airlines flights from Wisconsin to Portland, Maine

Our best United Airlines 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

momondo Fare Finder

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

What is the cheapest month to fly to Portland, Maine?

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

What airlines fly to Portland, Maine?

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

Cheap Wisconsin to Portland, Maine flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Wisconsin to Portland, Maine

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?

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

Fly your favorite airline to Portland

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Portland

List of cabin classes available on flights landing in Portland. Availability may vary depending on flight origin and airline.

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo

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According to popular flight searches on momondo this year

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