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Cheap flights from Portland, Maine to Wisconsin from $107

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland, Maine to Wisconsin departing on 3/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Portland, Maine to Wisconsin

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
7:22 pm - 7:57 amPWM-ORD
13h 35m2 stops
United Airlines Logo
10:53 am - 2:12 pmORD-PWM
2h 19mnonstop
$247United Airlines
Find Deal
Tue, Oct 28 - Wed, Oct 29
Multiple Airlines Logo
9:46 am - 5:04 pmPWM-ORD
8h 18m1 stop
Multiple Airlines Logo
7:49 pm - 9:06 amORD-PWM
12h 17m1 stop
$251Multiple Airlines
Find Deal
Fri, Dec 12 - Sun, Dec 14
Delta Logo
12:48 pm - 5:22 pmPWM-MSN
5h 34m1 stop
Delta Logo
5:29 am - 12:30 pmMSN-PWM
6h 01m1 stop
$259Delta
Find Deal
Fri, Nov 14 - Tue, Nov 18
Delta Logo
6:00 am - 12:32 pmPWM-MSN
7h 32m1 stop
Delta Logo
1:35 pm - 11:21 pmMSN-PWM
8h 46m2 stops
$264Delta
Find Deal
Thu, Nov 27 - Wed, Dec 3
American Airlines Logo
3:38 pm - 10:56 pmPWM-MSN
8h 18m1 stop
American Airlines Logo
3:46 pm - 11:51 pmMSN-PWM
7h 05m1 stop
$274American Airlines
Find Deal
Fri, Oct 24 - Thu, Oct 30
American Airlines Logo
1:05 pm - 8:39 pmPWM-ORD
8h 34m1 stop
American Airlines Logo
11:13 am - 8:14 pmORD-PWM
8h 01m1 stop
$278American Airlines
Find Deal
Tue, Oct 21 - Tue, Oct 28
JetBlue Logo
7:09 am - 12:22 pmPWM-ORD
6h 13m1 stop
JetBlue Logo
1:35 pm - 11:04 pmORD-PWM
8h 29m1 stop
$294JetBlue
Find Deal
Wed, Oct 22 - Fri, Oct 24
JetBlue Logo
7:09 am - 12:22 pmPWM-ORD
6h 13m1 stop
JetBlue Logo
10:08 am - 10:59 pmORD-PWM
11h 51m2 stops
$321JetBlue
Find Deal
Tue, Oct 21 - Sat, Oct 25
Southwest Logo
5:30 am - 9:30 amPWM-MKE
5h 00m1 stop
Southwest Logo
6:50 pm - 12:20 amMKE-PWM
4h 30m1 stop
$366Southwest
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Mon, Nov 3 - Fri, Nov 7
Southwest Logo
3:30 pm - 9:10 pmPWM-MSP
6h 40m1 stop
Southwest Logo
1:25 pm - 12:20 amMSP-PWM
9h 55m2 stops
$397Southwest
Find Deal
Mon, Dec 8 - Fri, Dec 12

Delta flights from Portland, Maine to Wisconsin

Our best Delta deals on Portland, Maine to Wisconsin flight tickets
Delta
Nov 14
PWM12:48 pmPortland
5h 34m
1 stop
MSN5:22 pmMadison Truax Field
Nov 18
MSN5:29 amMadison Truax Field
6h 01m
1 stop
PWM12:30 pmPortland
$259
Find similar
Delta
Nov 27
PWM6:00 amPortland
7h 32m
1 stop
MSN12:32 pmMadison Truax Field
Dec 3
MSN1:35 pmMadison Truax Field
8h 46m
2 stops
PWM11:21 pmPortland
$264
Find similar
Delta
Nov 12
PWM4:40 pmPortland
6h 05m
1 stop
MKE9:45 pmMilwaukee-Mitchell
Nov 27
MKE7:12 amMilwaukee-Mitchell
3h 56m
1 stop
PWM12:08 pmPortland
$274
Find similar

JetBlue flights from Portland, Maine to Wisconsin

Our best JetBlue deals on Portland, Maine to Wisconsin flight tickets
JetBlue
Oct 22
PWM7:09 amPortland
6h 13m
1 stop
ORD12:22 pmChicago O'Hare Intl
Oct 24
ORD1:35 pmChicago O'Hare Intl
8h 29m
1 stop
PWM11:04 pmPortland
$294
Find similar
JetBlue
Oct 21
PWM7:09 amPortland
6h 13m
1 stop
ORD12:22 pmChicago O'Hare Intl
Oct 25
ORD10:08 amChicago O'Hare Intl
11h 51m
2 stops
PWM10:59 pmPortland
$321
Find similar
JetBlue
Oct 18
PWM2:17 pmPortland
5h 08m
1 stop
ORD6:25 pmChicago O'Hare Intl
Oct 21
ORD1:35 pmChicago O'Hare Intl
8h 29m
1 stop
PWM11:04 pmPortland
$323
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine to Wisconsin that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated October 9, 2025.
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

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 10/28

7:22 pm-7:57 am

2 stops13h 35m

Chicago O'Hare Intl

Wed 10/29

10:53 am-2:12 pm

Nonstop2h 19m

$247

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 12/12

9:46 am-5:04 pm

1 stop8h 18m

Chicago O'Hare Intl

Sun 12/14

7:49 pm-9:06 am

1 stop12h 17m

$251

PortlandMadison

PWM - MSN

PWMMSN

Portland

Fri 11/14

12:48 pm-5:22 pm

1 stop5h 34m

Madison Truax Field

Tue 11/18

5:29 am-12:30 pm

1 stop6h 01m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

Thu 11/27

6:00 am-12:32 pm

1 stop7h 32m

Madison Truax Field

Wed 12/3

1:35 pm-11:21 pm

2 stops8h 46m

$264

PortlandMadison

PWM - MSN

PWMMSN

Portland

Fri 10/24

3:38 pm-10:56 pm

1 stop8h 18m

Madison Truax Field

Thu 10/30

3:46 pm-11:51 pm

1 stop7h 05m

$274

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 10/21

1:05 pm-8:39 pm

1 stop8h 34m

Chicago O'Hare Intl

Tue 10/28

11:13 am-8:14 pm

1 stop8h 01m

$278

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 10/22

7:09 am-12:22 pm

1 stop6h 13m

Chicago O'Hare Intl

Fri 10/24

1:35 pm-11:04 pm

1 stop8h 29m

$294

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 10/21

7:09 am-12:22 pm

1 stop6h 13m

Chicago O'Hare Intl

Sat 10/25

10:08 am-10:59 pm

2 stops11h 51m

$321

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Mon 11/3

5:30 am-9:30 am

1 stop5h 00m

Milwaukee-Mitchell

Fri 11/7

6:50 pm-12:20 am

1 stop4h 30m

$366

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Mon 12/8

3:30 pm-9:10 pm

1 stop6h 40m

Minneapolis St Paul

Fri 12/12

1:25 pm-12:20 am

2 stops9h 55m

$397

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Wisconsin from

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

What is the cheapest month to fly to Wisconsin?

If you aren’t able to travel during the month of January, then book flights to Wisconsin from Portland, Maine during February instead. Flights to Wisconsin in February, while not as cheap as those in January, still average around $366.

What is the cheapest day to depart on your flight to Wisconsin?

The cheapest day to depart from Portland, Maine to Wisconsin is on a Wednesday. Travelers who choose to depart for Wisconsin on a Wednesday will often find tickets for as low as $356. The most expensive day to fly to Wisconsin is Saturday, with ticket prices averaging around $530.

What is the cheapest time of day to depart on your flight to Wisconsin?

Our most recent data shows that the best time of day to fly to Wisconsin is in the evening. Flights from Portland, Maine to Wisconsin during this time can be as low as $173. Flights in the afternoon are often more expensive with an average ticket price of $398.

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

You could potentially save up to 23% 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

Fastest flight time

2h 51m

Direct flights

Every day

Airports in Wisconsin

2 airports
The fastest flight from Portland, Maine to Wisconsin takes 2h 51m
Direct flights go from Portland, Maine to Wisconsin every day.
There are 2 airports near Wisconsin: Chicago O'Hare Intl (ORD), Minneapolis St Paul (MSP)
Search flight deals

  • 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?

  • 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
American AirlinesPriceFrom $204Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights
DeltaPriceFrom $258Free CancellationRating
7.9
7,969 reviews
Search Delta flights
United AirlinesPriceFrom $258Free CancellationRating
7.4
8,968 reviews
Search United Airlines flights
SouthwestPriceFrom $311Free CancellationRating
8.0
4,237 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.

An easier way to manage your Wisconsin 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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