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

Delta, United Airlines, and Southwest are the most popular carriers operating from Portland to Wisconsin

What airlines fly to Wisconsin?

Delta, American Airlines and JetBlue are the top three most popular airlines that fly to Wisconsin from Portland, Maine according to our data. Delta is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Wisconsin. Keep in mind that there are 5 different airlines that fly to Wisconsin on a routine basis, so you have a few additional options to choose from.

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

Prices for flights from Portland Airport to Wisconsin are updated daily.

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

There are 4 operators available for flights from Portland Airport to Wisconsin as of November 2026.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Wisconsin.

What documentation or ID do you need to fly to Wisconsin?

The travel and health documents required for your trip to Wisconsin can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Wisconsin. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$294 Cheap Flights from Portland, Maine to Wisconsin in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Portland, Maine to Wisconsin

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:17 am - 1:13 pmPWM Portland-MKE Milwaukee-Mitchell

7h 56m1 stop New York LaGuardia

7:00 am - 12:04 pmMKE Milwaukee-Mitchell-PWM Portland

4h 04m1 stop Detroit Metropolitan Wayne County

$347Delta

Wed, Feb 10 - Wed, Feb 17

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

6h 01m1 stop New York LaGuardia

7:15 am - 12:59 pmMKE Milwaukee-Mitchell-PWM Portland

4h 44m1 stop New York LaGuardia

$347Delta

Tue, Feb 9 - Sat, Feb 13

6:00 am - 2:45 pmPWM Portland-GRB Green Bay Austin-Straubel

9h 45m2 stops Newark Chicago O'Hare Intl

9:45 am - 3:38 pmGRB Green Bay Austin-Straubel-PWM Portland

4h 53m1 stop Chicago O'Hare Intl

$354United Airlines

Wed, Dec 2 - Sat, Dec 12

4:47 pm - 9:15 pmPWM Portland-MSN Madison Truax Field

5h 28m1 stop Chicago O'Hare Intl

6:00 am - 1:38 pmMSN Madison Truax Field-PWM Portland

6h 38m1 stop Newark

$359United Airlines

Sat, Dec 5 - Tue, Dec 8

11:57 am - 7:51 pmPWM Portland-GRB Green Bay Austin-Straubel

8h 54m2 stops Washington, D.C. Reagan-National Chicago O'Hare Intl

10:00 am - 11:19 pmGRB Green Bay Austin-Straubel-PWM Portland

12h 19m2 stops Chicago O'Hare Intl Philadelphia

$359American Airlines

Wed, Dec 2 - Sat, Dec 12

6:00 am - 2:42 pmPWM Portland-MSN Madison Truax Field

9h 42m2 stops Philadelphia Chicago O'Hare Intl

5:00 am - 11:42 amMSN Madison Truax Field-PWM Portland

5h 42m1 stop Chicago O'Hare Intl

$364American Airlines

Sat, Dec 5 - Tue, Dec 8

5:20 am - 12:05 pmPWM Portland-MKE Milwaukee-Mitchell

7h 45m1 stop Baltimore/Washington

5:50 am - 3:15 pmMKE Milwaukee-Mitchell-PWM Portland

8h 25m2 stops Chicago Midway Nashville Intl

$426Southwest

Tue, Apr 6 - Wed, Apr 7

1:10 pm - 10:00 pmPWM Portland-MKE Milwaukee-Mitchell

9h 50m2 stops Baltimore/Washington Dallas Love Field

7:30 am - 5:15 pmMKE Milwaukee-Mitchell-PWM Portland

8h 45m2 stops Nashville Intl Baltimore/Washington

$431Southwest

Tue, Apr 6 - Wed, Apr 7

9:48 am - 9:50 amPWM Portland-MSN Madison Truax Field

25h 02m1 stop Orlando

6:10 pm - 9:08 amMSN Madison Truax Field-PWM Portland

13h 58m1 stop Orlando

$584Breeze Airways

Mon, Nov 30 - Thu, Dec 3

9:48 am - 9:50 amPWM Portland-MSN Madison Truax Field

25h 02m1 stop Orlando

6:10 pm - 4:55 pmMSN Madison Truax Field-PWM Portland

21h 45m2 stops Orlando Charleston

$643Breeze Airways

Mon, Nov 30 - Thu, Dec 3

Cheap last minute flights

Enter your travel dates to find the best prices.

6:17 am - 11:53 amPWM Portland-MSN Madison Truax Field

6h 36m1 stop Washington, D.C. Reagan-National

5:00 am - 11:56 amMSN Madison Truax Field-PWM Portland

5h 56m1 stop Chicago O'Hare Intl

$430American Airlines

Tue, Nov 17 - Sun, Nov 22

6:00 am - 2:41 pmPWM Portland-MSN Madison Truax Field

9h 41m2 stops Philadelphia Chicago O'Hare Intl

6:00 am - 11:56 amMSN Madison Truax Field-PWM Portland

4h 56m1 stop Chicago O'Hare Intl

$435American Airlines

Tue, Nov 17 - Sun, Nov 22

6:00 am - 4:25 pmPWM Portland-MSN Madison Truax Field

11h 25m2 stops New York John F Kennedy Intl Atlanta Hartsfield-Jackson

1:24 pm - 11:31 pmMSN Madison Truax Field-PWM Portland

9h 07m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

$440Delta

Tue, Nov 17 - Sun, Nov 22

6:17 am - 11:53 amPWM Portland-MSN Madison Truax Field

6h 36m1 stop Washington, D.C. Reagan-National

5:00 am - 11:56 amMSN Madison Truax Field-PWM Portland

5h 56m1 stop Chicago O'Hare Intl

$478American Airlines

Tue, Nov 17 - Sun, Nov 22

6:17 am - 2:41 pmPWM Portland-MSN Madison Truax Field

9h 24m2 stops Washington, D.C. Reagan-National Chicago O'Hare Intl

6:00 am - 11:56 amMSN Madison Truax Field-PWM Portland

4h 56m1 stop Chicago O'Hare Intl

$483American Airlines

Tue, Nov 17 - Sun, Nov 22

6:27 am - 4:25 pmPWM Portland-MSN Madison Truax Field

10h 58m2 stops New York LaGuardia Atlanta Hartsfield-Jackson

2:30 pm - 11:31 pmMSN Madison Truax Field-PWM Portland

8h 01m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

$488Delta

Tue, Nov 17 - Sun, Nov 22

6:00 am - 4:25 pmPWM Portland-MSN Madison Truax Field

11h 25m2 stops New York John F Kennedy Intl Atlanta Hartsfield-Jackson

1:24 pm - 11:31 pmMSN Madison Truax Field-PWM Portland

9h 07m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

$488Delta

Tue, Nov 17 - Sun, Nov 22

6:27 am - 4:25 pmPWM Portland-MSN Madison Truax Field

10h 58m2 stops New York LaGuardia Atlanta Hartsfield-Jackson

2:30 pm - 11:31 pmMSN Madison Truax Field-PWM Portland

8h 01m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

$498Delta

Tue, Nov 17 - Sun, Nov 22

3:25 pm - 9:25 pmPWM Portland-MKE Milwaukee-Mitchell

7h 00m1 stop Baltimore/Washington

10:45 am - 9:50 pmMKE Milwaukee-Mitchell-PWM Portland

10h 05m2 stops Tampa Baltimore/Washington

$690Southwest

Tue, Nov 17 - Thu, Nov 19

12:45 pm - 9:50 pmPWM Portland-MKE Milwaukee-Mitchell

10h 05m2 stops Baltimore/Washington Denver Intl

10:45 am - 9:50 pmMKE Milwaukee-Mitchell-PWM Portland

10h 05m2 stops Tampa Baltimore/Washington

$695Southwest

Tue, Nov 17 - Thu, Nov 19

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Delta flights from Portland, Maine to Wisconsin

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

Delta

Feb 9

PWM6:17 amPortland

7h 56m

1 stop

MKE1:13 pmMilwaukee-Mitchell

Feb 13

MKE7:00 amMilwaukee-Mitchell

4h 04m

1 stop

PWM12:04 pmPortland

$347

Delta

Feb 9

PWM11:38 amPortland

9h 52m

2 stops

MKE8:30 pmMilwaukee-Mitchell

Feb 13

MKE2:55 pmMilwaukee-Mitchell

5h 12m

1 stop

PWM9:07 pmPortland

$352

Delta

Feb 9

PWM11:38 amPortland

9h 52m

2 stops

MKE8:30 pmMilwaukee-Mitchell

Feb 17

MKE7:00 amMilwaukee-Mitchell

6h 23m

2 stops

PWM2:23 pmPortland

$357

United Airlines flights from Portland, Maine to Wisconsin

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

United Airlines

Dec 2

PWM6:00 amPortland

9h 45m

2 stops

GRB2:45 pmGreen Bay Austin-Straubel

Dec 12

GRB9:45 amGreen Bay Austin-Straubel

4h 53m

1 stop

PWM3:38 pmPortland

$354

United Airlines

Dec 4

PWM4:47 pmPortland

5h 28m

1 stop

MSN9:15 pmMadison Truax Field

Dec 8

MSN9:12 amMadison Truax Field

5h 26m

1 stop

PWM3:38 pmPortland

$359

United Airlines

Dec 4

PWM6:00 amPortland

9h 03m

2 stops

ATW2:03 pmAppleton Intl

Dec 7

ATW2:38 pmAppleton Intl

7h 46m

2 stops

PWM11:24 pmPortland

$369

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandMilwaukee

PWM Portland - MKE Milwaukee-Mitchell

PWMMKE

Portland

Wed 2/10

6:17 am-1:13 pm

1 stop7h 56m

Milwaukee-Mitchell

Wed 2/17

7:00 am-12:04 pm

1 stop4h 04m

$347

Quickest round-trip

PortlandMilwaukee

PWM Portland - MKE Milwaukee-Mitchell

PWMMKE

Portland

Tue 2/9

5:10 pm-10:11 pm

1 stop6h 01m

Milwaukee-Mitchell

Sat 2/13

7:15 am-12:59 pm

1 stop4h 44m

$347

PortlandGreen Bay

PWM Portland - GRB Green Bay Austin-Straubel

PWMGRB

Portland

Wed 12/2

6:00 am-2:45 pm

2 stops9h 45m

Green Bay Austin-Straubel

Sat 12/12

9:45 am-3:38 pm

1 stop4h 53m

$354

PortlandMadison

PWM Portland - MSN Madison Truax Field

PWMMSN

Portland

Sat 12/5

4:47 pm-9:15 pm

1 stop5h 28m

Madison Truax Field

Tue 12/8

6:00 am-1:38 pm

1 stop6h 38m

$359

PortlandGreen Bay

PWM Portland - GRB Green Bay Austin-Straubel

PWMGRB

Portland

Wed 12/2

11:57 am-7:51 pm

2 stops8h 54m

Green Bay Austin-Straubel

Sat 12/12

10:00 am-11:19 pm

2 stops12h 19m

$359

PortlandMadison

PWM Portland - MSN Madison Truax Field

PWMMSN

Portland

Sat 12/5

6:00 am-2:42 pm

2 stops9h 42m

Madison Truax Field

Tue 12/8

5:00 am-11:42 am

1 stop5h 42m

$364

PortlandMilwaukee

PWM Portland - MKE Milwaukee-Mitchell

PWMMKE

Portland

Tue 4/6

5:20 am-12:05 pm

1 stop7h 45m

Milwaukee-Mitchell

Wed 4/7

5:50 am-3:15 pm

2 stops8h 25m

$426

PortlandMilwaukee

PWM Portland - MKE Milwaukee-Mitchell

PWMMKE

Portland

Tue 4/6

1:10 pm-10:00 pm

2 stops9h 50m

Milwaukee-Mitchell

Wed 4/7

7:30 am-5:15 pm

2 stops8h 45m

$431

PortlandMadison

PWM Portland - MSN Madison Truax Field

PWMMSN

Portland

Mon 11/30

9:48 am-9:50 am

1 stop25h 02m

Madison Truax Field

Thu 12/3

6:10 pm-9:08 am

1 stop13h 58m

$584

PortlandMadison

PWM Portland - MSN Madison Truax Field

PWMMSN

Portland

Mon 11/30

9:48 am-9:50 am

1 stop25h 02m

Madison Truax Field

Thu 12/3

6:10 pm-4:55 pm

2 stops21h 45m

$643

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 Portland, Maine to Wisconsin

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

What is the cheapest month to fly to Wisconsin?

If you aren’t able to travel during the month of February, then book flights to Wisconsin from Portland, Maine during January instead. Flights to Wisconsin in January, while not as cheap as those in February, still average around $386.

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

You could potentially save up to 50% on your flight if you consider stops on a Portland, Maine to Wisconsin flight.

Cheap Portland, Maine to Wisconsin flight deals and tips

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

Best Price Found	$294
Fastest flight time	2h 57m
Direct flights	None

The best one-way flight to Wisconsin from Portland, Maine in the past 72 hours is $294. The best round-trip flight deal from Portland, Maine to Wisconsin found on momondo in the last 72 hours is $347.

The fastest flight from Portland, Maine to Wisconsin takes 2h 57m

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

Search flight deals

Frequently asked questions about flying from Portland, Maine to Wisconsin

When did momondo last update prices for flights from Portland Airport to Wisconsin?
Prices for flights from Portland Airport to Wisconsin are updated daily.
How many operators does momondo search for flights from Portland Airport to Wisconsin?
There are 4 operators available for flights from Portland Airport to Wisconsin as of November 2026.
How old do you have to be to fly from Portland Airport to Wisconsin?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Wisconsin.
What documentation or ID do you need to fly to Wisconsin?
The travel and health documents required for your trip to Wisconsin can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Wisconsin. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Portland, Maine to Wisconsin

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $170	Free Cancellation	Rating 7.8 8,712 reviews	Search Delta flights
United Airlines	PriceFrom $198	Free Cancellation	Rating 7.3 10,486 reviews	Search United Airlines flights
American Airlines	PriceFrom $290	Free Cancellation	Rating 7.0 12,233 reviews	Search American Airlines flights
Southwest	PriceFrom $343	Free Cancellation	Rating 8.0 4,218 reviews	Search Southwest flights

Why use momondo?

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

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

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

Flights from Portland to Wisconsin with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo provides multiple filters to help you find the best flight to Wisconsin from Portland. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are simply researching potential flights to Wisconsin, momondo offers a useful price alert feature which will track prices for flights to Wisconsin from Portland and alert you when they change.