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

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

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 10m on average. If you fly from Madison (another popular airport in Wisconsin) to Boston, then the average flight time is 2h 27m.

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 38% 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 September 2026, 81 flights take off from Wisconsin and land in Portland, Maine each week. The most common flight departure day for this route is Mon, with 15% 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 5 operators available for flights from Wisconsin to Portland Airport as of September 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.

$139 Cheap Flights from Wisconsin to Portland, Maine in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Wisconsin to Portland

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:18 pm - 9:54 pmORD Chicago O'Hare Intl-PWM Portland

2h 36mnonstop

7:58 am - 10:00 amPWM Portland-ORD Chicago O'Hare Intl

3h 02mnonstop

$297United Airlines

Wed, Oct 14 - Thu, Oct 15

2:10 pm - 5:54 pmORD Chicago O'Hare Intl-PWM Portland

2h 44mnonstop

6:00 am - 7:57 amPWM Portland-ORD Chicago O'Hare Intl

2h 57mnonstop

$297United Airlines

Sat, Sep 19 - Wed, Sep 23

7:59 pm - 11:43 pmORD Chicago O'Hare Intl-PWM Portland

2h 44mnonstop

5:45 pm - 7:55 pmPWM Portland-ORD Chicago O'Hare Intl

3h 10mnonstop

$297American Airlines

Sat, Oct 17 - Tue, Oct 20

7:59 pm - 11:43 pmORD Chicago O'Hare Intl-PWM Portland

2h 44mnonstop

5:45 pm - 7:55 pmPWM Portland-ORD Chicago O'Hare Intl

3h 10mnonstop

$297American Airlines

Sat, Oct 17 - Sat, Oct 24

1:37 pm - 9:00 pmMSN Madison Truax Field-PWM Portland

6h 23m1 stop Atlanta Hartsfield-Jackson

6:01 am - 12:31 pmPWM Portland-MSN Madison Truax Field

7h 30m1 stop Atlanta Hartsfield-Jackson

$301Delta

Sat, Oct 17 - Sat, Oct 24

1:37 pm - 12:10 amMSN Madison Truax Field-PWM Portland

9h 33m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl

12:43 pm - 4:48 pmPWM Portland-MSN Madison Truax Field

5h 05m1 stop New York LaGuardia

$306Delta

Sat, Oct 17 - Sat, Oct 24

8:25 am - 12:06 pmMSP Minneapolis St Paul-PWM Portland

2h 41mnonstop

5:09 pm - 8:05 amPWM Portland-MSP Minneapolis St Paul

39h 56m3 stops Raleigh-Durham Atlanta Hartsfield-Jackson Dallas/Fort Worth

$306Multiple Airlines

Mon, Oct 19 - Tue, Oct 27

8:25 am - 12:06 pmMSP Minneapolis St Paul-PWM Portland

2h 41mnonstop

5:09 pm - 8:05 amPWM Portland-MSP Minneapolis St Paul

39h 56m3 stops Raleigh-Durham Detroit Metropolitan Wayne County Dallas/Fort Worth

$306Multiple Airlines

Mon, Oct 19 - Tue, Oct 27

10:30 am - 8:35 pmMKE Milwaukee-Mitchell-PWM Portland

9h 05m2 stops Nashville Intl Baltimore/Washington

7:20 am - 4:50 pmPWM Portland-MKE Milwaukee-Mitchell

10h 30m2 stops Baltimore/Washington Chicago Midway

$335Southwest

Wed, Oct 28 - Sat, Oct 31

3:15 pm - 10:10 pmMKE Milwaukee-Mitchell-PWM Portland

5h 55m1 stop Chicago Midway

5:55 am - 11:55 amPWM Portland-MKE Milwaukee-Mitchell

7h 00m1 stop Baltimore/Washington

$385Southwest

Tue, Sep 22 - Thu, Sep 24

Cheap last minute flights

Enter your travel dates to find the best prices.

11:58 am - 3:27 pmORD Chicago O'Hare Intl-PWM Portland

2h 29mnonstop

12:09 pm - 2:09 pmPWM Portland-ORD Chicago O'Hare Intl

3h 00mnonstop

$338American Airlines

Sat, Sep 5 - Sun, Sep 6

4:00 pm - 9:57 pmORD Chicago O'Hare Intl-PWM Portland

4h 57m1 stop Philadelphia

6:09 pm - 8:30 pmPWM Portland-ORD Chicago O'Hare Intl

3h 21mnonstop

$348American Airlines

Sat, Sep 5 - Sun, Sep 6

6:59 am - 12:02 pmORD Chicago O'Hare Intl-PWM Portland

4h 03m1 stop Detroit Metropolitan Wayne County

6:30 am - 12:59 pmPWM Portland-ORD Chicago O'Hare Intl

7h 29m1 stop New York LaGuardia

$357Delta

Sun, Sep 6 - Thu, Sep 10

6:00 am - 2:23 pmORD Chicago O'Hare Intl-PWM Portland

7h 23m1 stop New York John F Kennedy Intl

1:59 pm - 6:04 pmPWM Portland-ORD Chicago O'Hare Intl

5h 05m1 stop New York LaGuardia

$357Delta

Sun, Sep 6 - Thu, Sep 10

5:50 pm - 9:23 pmORD Chicago O'Hare Intl-PWM Portland

2h 33mnonstop

6:00 am - 7:57 amPWM Portland-ORD Chicago O'Hare Intl

2h 57mnonstop

$417United Airlines

Sun, Sep 6 - Sun, Sep 13

5:50 pm - 9:23 pmORD Chicago O'Hare Intl-PWM Portland

2h 33mnonstop

6:00 am - 7:57 amPWM Portland-ORD Chicago O'Hare Intl

2h 57mnonstop

$417United Airlines

Fri, Sep 4 - Wed, Sep 9

7:10 pm - 9:12 amMSP Minneapolis St Paul-PWM Portland

13h 02m1 stop Orlando

6:00 am - 8:31 amPWM Portland-MSP Minneapolis St Paul

27h 31m2 stops Cincinnati Cinci./N. Kentucky Atlanta Hartsfield-Jackson

$601Multiple Airlines

Sun, Sep 6 - Fri, Sep 11

12:50 pm - 9:05 pmMSP Minneapolis St Paul-PWM Portland

7h 15m2 stops Chicago Midway Baltimore/Washington

2:10 pm - 9:25 pmPWM Portland-MSP Minneapolis St Paul

8h 15m1 stop Nashville Intl

$604Southwest

Sat, Sep 5 - Fri, Sep 11

1:00 pm - 10:55 pmMSP Minneapolis St Paul-PWM Portland

8h 55m2 stops Denver Intl Baltimore/Washington

2:10 pm - 10:30 pmPWM Portland-MSP Minneapolis St Paul

9h 20m2 stops Nashville Intl Lambert-St Louis

$609Southwest

Sun, Sep 6 - Fri, Sep 11

7:10 pm - 9:12 amMSP Minneapolis St Paul-PWM Portland

13h 02m1 stop Orlando

6:00 am - 6:01 pmPWM Portland-MSP Minneapolis St Paul

13h 01m2 stops Cincinnati Cinci./N. Kentucky Dallas/Fort Worth

$653Multiple Airlines

Sun, Sep 6 - Fri, Sep 11

Cheap direct flights

Enter your travel dates to find the best prices.

6:18 pm - 9:54 pmORD Chicago O'Hare Intl-PWM Portland

2h 36mnonstop

7:58 am - 10:00 amPWM Portland-ORD Chicago O'Hare Intl

3h 02mnonstop

$297United Airlines

Wed, Oct 14 - Thu, Oct 15

2:10 pm - 5:54 pmORD Chicago O'Hare Intl-PWM Portland

2h 44mnonstop

6:00 am - 7:57 amPWM Portland-ORD Chicago O'Hare Intl

2h 57mnonstop

$297United Airlines

Sat, Sep 19 - Wed, Sep 23

7:59 pm - 11:43 pmORD Chicago O'Hare Intl-PWM Portland

2h 44mnonstop

5:45 pm - 7:55 pmPWM Portland-ORD Chicago O'Hare Intl

3h 10mnonstop

$297American Airlines

Sat, Oct 17 - Tue, Oct 20

7:59 pm - 11:43 pmORD Chicago O'Hare Intl-PWM Portland

2h 44mnonstop

5:45 pm - 7:55 pmPWM Portland-ORD Chicago O'Hare Intl

3h 10mnonstop

$297American Airlines

Sat, Oct 17 - Sat, Oct 24

7:59 pm - 11:43 pmORD Chicago O'Hare Intl-PWM Portland

2h 44mnonstop

7:00 am - 9:04 amPWM Portland-ORD Chicago O'Hare Intl

3h 04mnonstop

$297American Airlines

Sat, Oct 17 - Thu, Oct 22

6:18 pm - 9:54 pmORD Chicago O'Hare Intl-PWM Portland

2h 36mnonstop

6:00 am - 7:57 amPWM Portland-ORD Chicago O'Hare Intl

2h 57mnonstop

$308United Airlines

Tue, Oct 13 - Fri, Oct 16

7:00 am - 10:45 amMSP Minneapolis St Paul-PWM Portland

2h 45mnonstop

11:55 am - 2:02 pmPWM Portland-MSP Minneapolis St Paul

3h 07mnonstop

$389Delta

Tue, Sep 29 - Wed, Oct 7

7:00 am - 10:50 amMSP Minneapolis St Paul-PWM Portland

2h 50mnonstop

11:55 am - 2:02 pmPWM Portland-MSP Minneapolis St Paul

3h 07mnonstop

$389Delta

Sat, Oct 17 - Wed, Oct 21

11:10 am - 2:51 pmMSP Minneapolis St Paul-PWM Portland

2h 41mnonstop

12:16 pm - 2:19 pmPWM Portland-MSP Minneapolis St Paul

3h 03mnonstop

$402Sun Country Air

Sun, Sep 20 - Thu, Oct 1

7:15 am - 10:59 amMSP Minneapolis St Paul-PWM Portland

2h 44mnonstop

3:52 pm - 5:55 pmPWM Portland-MSP Minneapolis St Paul

3h 03mnonstop

$416Sun Country Air

Thu, Sep 17 - Sun, Sep 20

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American Airlines flights from Wisconsin to Portland, Maine

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

American Airlines

Oct 17

ORD7:59 pmChicago O'Hare Intl

2h 44m

PWM11:43 pmPortland

Oct 20

PWM5:45 pmPortland

3h 10m

ORD7:55 pmChicago O'Hare Intl

$297

American Airlines

Oct 13

MSN6:17 pmMadison Truax Field

4h 42m

1 stop

PWM11:59 pmPortland

Oct 21

PWM5:37 pmPortland

6h 48m

1 stop

MSN11:25 pmMadison Truax Field

$301

American Airlines

Sep 25

MSN4:23 pmMadison Truax Field

6h 22m

1 stop

PWM11:45 pmPortland

Sep 30

PWM6:00 amPortland

6h 43m

1 stop

MSN11:43 amMadison Truax Field

$315

Southwest flights from Wisconsin to Portland, Maine

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

Southwest

Oct 28

MKE10:30 amMilwaukee-Mitchell

9h 05m

2 stops

PWM8:35 pmPortland

Oct 31

PWM7:20 amPortland

10h 30m

2 stops

MKE4:50 pmMilwaukee-Mitchell

$335

Southwest

Sep 22

MKE3:15 pmMilwaukee-Mitchell

5h 55m

1 stop

PWM10:10 pmPortland

Sep 24

PWM5:55 amPortland

7h 00m

1 stop

MKE11:55 amMilwaukee-Mitchell

$385

Southwest

Sep 22

MKE10:30 amMilwaukee-Mitchell

9h 45m

2 stops

PWM9:15 pmPortland

Sep 24

PWM3:40 pmPortland

6h 05m

1 stop

MKE8:45 pmMilwaukee-Mitchell

$386

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

ChicagoPortland

ORD Chicago O'Hare Intl - PWM Portland

ORDPWM

Chicago O'Hare Intl

Wed 10/14

6:18 pm-9:54 pm

Nonstop2h 36m

Portland

Thu 10/15

7:58 am-10:00 am

Nonstop3h 02m

$297

ChicagoPortland

ORD Chicago O'Hare Intl - PWM Portland

ORDPWM

Chicago O'Hare Intl

Sat 9/19

2:10 pm-5:54 pm

Nonstop2h 44m

Portland

Wed 9/23

6:00 am-7:57 am

Nonstop2h 57m

$297

ChicagoPortland

ORD Chicago O'Hare Intl - PWM Portland

ORDPWM

Chicago O'Hare Intl

Sat 10/17

7:59 pm-11:43 pm

Nonstop2h 44m

Portland

Tue 10/20

5:45 pm-7:55 pm

Nonstop3h 10m

$297

ChicagoPortland

ORD Chicago O'Hare Intl - PWM Portland

ORDPWM

Chicago O'Hare Intl

Sat 10/17

7:59 pm-11:43 pm

Nonstop2h 44m

Portland

Sat 10/24

5:45 pm-7:55 pm

Nonstop3h 10m

$297

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Sat 10/17

1:37 pm-9:00 pm

1 stop6h 23m

Portland

Sat 10/24

6:01 am-12:31 pm

1 stop7h 30m

$301

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Sat 10/17

1:37 pm-12:10 am

2 stops9h 33m

Portland

Sat 10/24

12:43 pm-4:48 pm

1 stop5h 05m

$306

MinneapolisPortland

MSP Minneapolis St Paul - PWM Portland

MSPPWM

Minneapolis St Paul

Mon 10/19

8:25 am-12:06 pm

Nonstop2h 41m

Portland

Tue 10/27

5:09 pm-8:05 am

3 stops39h 56m

$306

MinneapolisPortland

MSP Minneapolis St Paul - PWM Portland

MSPPWM

Minneapolis St Paul

Mon 10/19

8:25 am-12:06 pm

Nonstop2h 41m

Portland

Tue 10/27

5:09 pm-8:05 am

3 stops39h 56m

$306

MilwaukeePortland

MKE Milwaukee-Mitchell - PWM Portland

MKEPWM

Milwaukee-Mitchell

Wed 10/28

10:30 am-8:35 pm

2 stops9h 05m

Portland

Sat 10/31

7:20 am-4:50 pm

2 stops10h 30m

$335

MilwaukeePortland

MKE Milwaukee-Mitchell - PWM Portland

MKEPWM

Milwaukee-Mitchell

Tue 9/22

3:15 pm-10:10 pm

1 stop5h 55m

Portland

Thu 9/24

5:55 am-11:55 am

1 stop7h 00m

$385

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 May is also cheap. Prices for this month can be found on momondo for an average of $408.

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	$139
Fastest flight time	2h 26m
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 $139. The best round-trip flight deal from Wisconsin to Portland, Maine found on momondo in the last 72 hours is $297.

The fastest flight from Wisconsin to Portland, Maine takes 2h 26m

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

There is 1 airport in Portland, Maine. From Wisconsin there are direct flights to Portland (PWM).

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 5 operators available for flights from Wisconsin to Portland Airport as of September 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 8,538 reviews	Search Delta flights
United Airlines	PriceFrom $276	Free Cancellation	Rating 7.4 10,157 reviews	Search United Airlines flights
American Airlines	PriceFrom $290	Free Cancellation	Rating 7.1 12,023 reviews	Search American Airlines flights
Southwest	PriceFrom $386	Free Cancellation	Rating 8.0 4,191 reviews	Search Southwest flights

North Conway

Boothbay Harbor

Jackson

Lewiston

Brunswick

Freeport

Conway

Auburn

Gorham

Bartlett

Windham

Bath

Intervale

Oxford

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.

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Rockland Knox County Regional Airport

Cheap flights from Wisconsin to Portland from $139

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 9/20. 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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American Airlines flights from Wisconsin to Portland, Maine

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

Southwest flights from Wisconsin to Portland, Maine

Our best Southwest 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.

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

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

Airports in Portland, Maine

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.

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

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