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Cheap flights from Wisconsin to Portland from $76

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 10/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

United Airlines Logo
5:55 pm - 11:59 pmORD-PWM
5h 04m1 stop
United Airlines Logo
4:54 pm - 6:55 pmPWM-ORD
3h 01mnonstop
$241United Airlines
Find Deal
mié., oct. 22 - mié., oct. 29
American Airlines Logo
6:06 am - 11:46 amORD-PWM
4h 40m1 stop
American Airlines Logo
5:43 am - 10:58 amPWM-ORD
6h 15m1 stop
$250American Airlines
Find Deal
mié., nov. 5 - mié., nov. 12
Delta Logo
10:30 am - 12:05 amORD-PWM
12h 35m2 stops
Delta Logo
1:46 pm - 8:37 pmPWM-ORD
7h 51m1 stop
$256Delta
Find Deal
sáb., oct. 18 - mar., oct. 28
Multiple Airlines Logo
2:41 pm - 10:41 amORD-PWM
19h 00m1 stop
Multiple Airlines Logo
11:16 am - 9:33 pmPWM-ORD
11h 17m1 stop
$259Multiple Airlines
Find Deal
vie., oct. 24 - mié., oct. 29
Delta Logo
5:20 am - 4:03 pmORD-PWM
9h 43m2 stops
Delta Logo
2:38 pm - 11:58 pmPWM-ORD
10h 20m2 stops
$261Delta
Find Deal
mié., nov. 5 - sáb., nov. 8
Multiple Airlines Logo
1:50 pm - 10:41 amORD-PWM
19h 51m1 stop
Multiple Airlines Logo
6:29 pm - 8:13 amPWM-ORD
14h 44m1 stop
$266Multiple Airlines
Find Deal
vie., nov. 14 - mar., nov. 18
JetBlue Logo
1:36 pm - 11:04 pmORD-PWM
8h 28m1 stop
JetBlue Logo
7:09 am - 12:22 pmPWM-ORD
6h 13m1 stop
$268JetBlue
Find Deal
vie., oct. 17 - mié., oct. 22
JetBlue Logo
1:35 pm - 11:04 pmORD-PWM
8h 29m1 stop
JetBlue Logo
2:17 pm - 8:51 pmPWM-ORD
7h 34m1 stop
$269JetBlue
Find Deal
mié., oct. 15 - vie., oct. 17
Southwest Logo
1:30 pm - 12:05 amORD-PWM
9h 35m2 stops
Southwest Logo
5:45 am - 12:45 pmPWM-ORD
8h 00m2 stops
$313Southwest
Find Deal
jue., oct. 23 - mar., oct. 28
Southwest Logo
6:10 am - 2:55 pmMSP-PWM
7h 45m1 stop
Southwest Logo
3:30 pm - 9:10 pmPWM-MSP
6h 40m1 stop
$339Southwest
Find Deal
lun., nov. 3 - mié., nov. 5

American Airlines flights from Wisconsin to Portland, Maine

Our best American Airlines deals on Wisconsin to Portland, Maine flight tickets
American Airlines
Nov 5
ORD6:06 amChicago O'Hare Intl
4h 40m
1 stop
PWM11:46 amPortland
Nov 12
PWM5:43 amPortland
6h 15m
1 stop
ORD10:58 amChicago O'Hare Intl
$250
Find similar
American Airlines
Oct 22
MSN5:10 pmMadison Truax Field
4h 38m
1 stop
PWM10:48 pmPortland
Oct 25
PWM5:59 pmPortland
6h 52m
1 stop
MSN11:51 pmMadison Truax Field
$259
Find similar
American Airlines
Oct 21
ORD7:58 amChicago O'Hare Intl
2h 30m
PWM11:28 amPortland
Oct 25
PWM3:28 pmPortland
2h 56m
ORD5:24 pmChicago O'Hare Intl
$265
Find similar

Sun Country Air flights from Wisconsin to Portland, Maine

Our best Sun Country Air deals on Wisconsin to Portland, Maine flight tickets
Sun Country Air
Sep 28
MSP11:12 amMinneapolis St Paul
2h 40m
PWM2:52 pmPortland
Oct 2
PWM12:33 pmPortland
3h 02m
MSP2:35 pmMinneapolis St Paul
$304
Find similar
Sun Country Air
Oct 12
MSP7:48 amMinneapolis St Paul
2h 43m
PWM11:31 amPortland
Oct 16
PWM12:40 pmPortland
3h 02m
MSP2:42 pmMinneapolis St Paul
$315
Find similar
Sun Country Air
Sep 28
MSP11:12 amMinneapolis St Paul
2h 40m
PWM2:52 pmPortland
Oct 2
PWM12:33 pmPortland
3h 02m
MSP2:35 pmMinneapolis St Paul
$327
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Wisconsin to Portland, Maine 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 septiembre 23, 2025.
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

mié. 10/22

5:55 pm-11:59 pm

1 stop5h 04m

Portland

mié. 10/29

4:54 pm-6:55 pm

Nonstop3h 01m

$241

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

mié. 11/5

6:06 am-11:46 am

1 stop4h 40m

Portland

mié. 11/12

5:43 am-10:58 am

1 stop6h 15m

$250

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

sáb. 10/18

10:30 am-12:05 am

2 stops12h 35m

Portland

mar. 10/28

1:46 pm-8:37 pm

1 stop7h 51m

$256

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

vie. 10/24

2:41 pm-10:41 am

1 stop19h 00m

Portland

mié. 10/29

11:16 am-9:33 pm

1 stop11h 17m

$259

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

mié. 11/5

5:20 am-4:03 pm

2 stops9h 43m

Portland

sáb. 11/8

2:38 pm-11:58 pm

2 stops10h 20m

$261

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

vie. 11/14

1:50 pm-10:41 am

1 stop19h 51m

Portland

mar. 11/18

6:29 pm-8:13 am

1 stop14h 44m

$266

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

vie. 10/17

1:36 pm-11:04 pm

1 stop8h 28m

Portland

mié. 10/22

7:09 am-12:22 pm

1 stop6h 13m

$268

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

mié. 10/15

1:35 pm-11:04 pm

1 stop8h 29m

Portland

vie. 10/17

2:17 pm-8:51 pm

1 stop7h 34m

$269

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

jue. 10/23

1:30 pm-12:05 am

2 stops9h 35m

Portland

mar. 10/28

5:45 am-12:45 pm

2 stops8h 00m

$313

MinneapolisPortland

MSP - PWM

MSPPWM

Minneapolis St Paul

lun. 11/3

6:10 am-2:55 pm

1 stop7h 45m

Portland

mié. 11/5

3:30 pm-9:10 pm

1 stop6h 40m

$339

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 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?

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 $393 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 56% 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?

  • 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 AirlinesPriceFrom $238Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,244 reviews
Search Southwest flights
DeltaPriceFrom $248Free CancellationRating
7.9
7,974 reviews
Search Delta flights
United AirlinesPriceFrom $267Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Boothbay Harbor
Jackson
Conway
Freeport
Lewiston
Bartlett
Brunswick
Gorham
Auburn
Intervale
Windham
Bath
Oxford
Georgetown
Tamworth
Falmouth

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

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