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Cheap flights from Cleveland to Boston from $160

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Cleveland to Boston departing on 12/31. 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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Multiple Airlines Logo
4:53 pm - 10:22 am
CLE
-
PWM
17h 29m1 stop
Multiple Airlines Logo
5:06 pm - 8:57 pm
PWM
-
CLE
27h 51m2 stops
$296Multiple Airlines
Tue, Jan 6 - Fri, Jan 9
United Airlines Logo
7:13 pm - 11:30 pm
CLE
-
PWM
4h 17m1 stop
United Airlines Logo
8:35 am - 2:59 pm
PWM
-
CLE
6h 24m1 stop
$321United Airlines
Fri, Jan 9 - Sun, Jan 18
Multiple Airlines Logo
4:53 pm - 10:22 am
CLE
-
PWM
17h 29m1 stop
Multiple Airlines Logo
9:47 am - 6:19 pm
PWM
-
CLE
8h 32m1 stop
$331Multiple Airlines
Tue, Jan 6 - Fri, Jan 9
Delta Logo
7:29 pm - 11:22 pm
CLE
-
PWM
3h 53m1 stop
Delta Logo
6:00 am - 1:07 pm
PWM
-
CLE
7h 07m1 stop
$344Delta
Mon, Jan 12 - Fri, Jan 16
Delta Logo
7:15 am - 1:54 pm
CLE
-
PWM
6h 39m1 stop
Delta Logo
6:50 pm - 12:37 am
PWM
-
CLE
5h 47m1 stop
$367Delta
Fri, Jun 5 - Mon, Jun 8
Southwest Logo
8:40 am - 10:15 pm
CLE
-
PWM
13h 35m2 stops
Southwest Logo
12:45 pm - 8:50 pm
PWM
-
CLE
8h 05m2 stops
$388Southwest
Tue, Jan 6 - Fri, Jan 9
United Airlines Logo
10:32 am - 2:31 pm
CLE
-
PWM
3h 59m1 stop
United Airlines Logo
8:40 am - 2:59 pm
PWM
-
CLE
6h 19m1 stop
$391United Airlines
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
6:15 am - 2:55 pm
CLE
-
PWM
8h 40m2 stops
Southwest Logo
12:45 pm - 10:10 pm
PWM
-
CLE
9h 25m2 stops
$424Southwest
Fri, Jan 9 - Sun, Jan 18
Southwest Logo
4:45 pm - 10:10 pm
CLE
-
PWM
5h 25m1 stop
Southwest Logo
5:35 am - 2:25 pm
PWM
-
CLE
8h 50m2 stops
$439Southwest
Fri, Jun 5 - Mon, Jun 8
United Airlines Logo
8:00 am - 1:56 pm
CLE
-
PWM
5h 56m1 stop
United Airlines Logo
3:12 pm - 9:54 am
PWM
-
CLE
18h 42m2 stops
$444United Airlines
Mon, Jan 12 - Fri, Jan 16

United Airlines flights from Cleveland to Portland, Maine

Our best United Airlines deals on Cleveland to Portland, Maine flight tickets
United Airlines
Jan 9
CLE7:13 pmCleveland Hopkins Intl
4h 17m
1 stop
PWM11:30 pmPortland
Jan 18
PWM8:35 amPortland
6h 24m
1 stop
CLE2:59 pmCleveland Hopkins Intl
$321
Find similar
United Airlines
Jan 8
CLE10:32 amCleveland Hopkins Intl
3h 59m
1 stop
PWM2:31 pmPortland
Jan 12
PWM8:40 amPortland
6h 19m
1 stop
CLE2:59 pmCleveland Hopkins Intl
$391
Find similar
United Airlines
Jan 12
CLE8:00 amCleveland Hopkins Intl
5h 56m
1 stop
PWM1:56 pmPortland
Jan 16
PWM3:12 pmPortland
18h 42m
2 stops
CLE9:54 amCleveland Hopkins Intl
$444
Find similar

American Airlines flights from Cleveland to Portland, Maine

Our best American Airlines deals on Cleveland to Portland, Maine flight tickets
American Airlines
Dec 29
CLE6:46 pmCleveland Hopkins Intl
4h 09m
1 stop
PWM10:55 pmPortland
Jan 2
PWM6:41 pmPortland
4h 33m
1 stop
CLE11:14 pmCleveland Hopkins Intl
$447
Find similar
American Airlines
Dec 19
CLE4:14 pmCleveland Hopkins Intl
6h 41m
1 stop
PWM10:55 pmPortland
Dec 20
PWM5:20 pmPortland
7h 05m
2 stops
CLE12:25 amCleveland Hopkins Intl
$826
Find similar
American Airlines
Dec 19
CLE1:28 pmCleveland Hopkins Intl
10h 14m
2 stops
PWM11:42 pmPortland
Dec 20
PWM5:20 pmPortland
7h 05m
2 stops
CLE12:25 amCleveland Hopkins Intl
$962
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Cleveland 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 December 15, 2025.
Use the filters below to find and compare flights from Cleveland to Portland, Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ClevelandPortland

CLE - PWM

CLEPWM

Cleveland Hopkins Intl

Tue 1/6

4:53 pm-10:22 am

1 stop17h 29m

Portland

Fri 1/9

5:06 pm-8:57 pm

2 stops27h 51m

$296

ClevelandPortland

CLE - PWM

CLEPWM

Cleveland Hopkins Intl

Fri 1/9

7:13 pm-11:30 pm

1 stop4h 17m

Portland

Sun 1/18

8:35 am-2:59 pm

1 stop6h 24m

$321

ClevelandPortland

CLE - PWM

CLEPWM

Cleveland Hopkins Intl

Tue 1/6

4:53 pm-10:22 am

1 stop17h 29m

Portland

Fri 1/9

9:47 am-6:19 pm

1 stop8h 32m

$331

ClevelandPortland

CLE - PWM

CLEPWM

Cleveland Hopkins Intl

Mon 1/12

7:29 pm-11:22 pm

1 stop3h 53m

Portland

Fri 1/16

6:00 am-1:07 pm

1 stop7h 07m

$344

ClevelandPortland

CLE - PWM

CLEPWM

Cleveland Hopkins Intl

Fri 6/5

7:15 am-1:54 pm

1 stop6h 39m

Portland

Mon 6/8

6:50 pm-12:37 am

1 stop5h 47m

$367

ClevelandPortland

CLE - PWM

CLEPWM

Cleveland Hopkins Intl

Tue 1/6

8:40 am-10:15 pm

2 stops13h 35m

Portland

Fri 1/9

12:45 pm-8:50 pm

2 stops8h 05m

$388

ClevelandPortland

CLE - PWM

CLEPWM

Cleveland Hopkins Intl

Thu 1/8

10:32 am-2:31 pm

1 stop3h 59m

Portland

Mon 1/12

8:40 am-2:59 pm

1 stop6h 19m

$391

ClevelandPortland

CLE - PWM

CLEPWM

Cleveland Hopkins Intl

Fri 1/9

6:15 am-2:55 pm

2 stops8h 40m

Portland

Sun 1/18

12:45 pm-10:10 pm

2 stops9h 25m

$424

ClevelandPortland

CLE - PWM

CLEPWM

Cleveland Hopkins Intl

Fri 6/5

4:45 pm-10:10 pm

1 stop5h 25m

Portland

Mon 6/8

5:35 am-2:25 pm

2 stops8h 50m

$439

ClevelandPortland

CLE - PWM

CLEPWM

Cleveland Hopkins Intl

Mon 1/12

8:00 am-1:56 pm

1 stop5h 56m

Portland

Fri 1/16

3:12 pm-9:54 am

2 stops18h 42m

$444

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 Boston from

How to get the cheapest flight ticket from Cleveland 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 month to fly to Portland, Maine?

The cheapest month to fly to Portland, Maine from Cleveland is in February. Flight prices, which tend to average around $336, 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 February, then flying in November is also cheap. Prices for this month can be found on momondo for an average of $340.

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 Cleveland is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $342. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Thursday is the most expensive day to depart from Cleveland because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $409.

What is the cheapest time of day to depart on your flight to Portland, Maine?

At noon is the cheapest time of day to fly from Cleveland to Portland, Maine when you can find flight prices for as low as $353. Flying to Portland, Maine at noon 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 $376. 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 Cleveland when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland, Maine for around $376 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland, Maine from Cleveland for as low as $303 on momondo.

How have Cleveland to Portland, Maine flight prices changed over time?

As of December 2025, prices for Cleveland to Portland, Maine flights are approximately 60% more expensive when compared to flights at the same time last year.

When to book flights from Cleveland to Portland, Maine

Are you open to changing your travel dates? Check out the ideal times to fly from Cleveland to Portland, Maine according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Cleveland to Portland, Maine (CLE to PWM) flight deals and tips

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

Fastest flight time

3h 59m

Direct flights

None
The fastest flight from Cleveland to Portland, Maine takes 3h 59m
There are no direct flights from Cleveland to Portland, Maine. There are no popular flight routes from Cleveland to Portland, Maine.
Search flight deals

  • How far is Cleveland Hopkins Intl to Portland by plane?

    The straight-line distance from Cleveland Hopkins Intl to Portland is 599.8 mi. In terms of flight time, this usually takes a little over 3h 59m.

  • When did momondo last update prices for flights from Cleveland Hopkins Intl Airport to Portland Airport?

    Prices for flights from Cleveland Hopkins Intl Airport to Portland Airport were last updated today.

  • How many operators does momondo search for flights from Cleveland Hopkins Intl Airport to Portland Airport?

  • How old do you have to be to fly from Cleveland Hopkins Intl Airport to Portland Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Cleveland Hopkins Intl Airport to Portland Airport.

  • What documentation or ID do you need to fly to Portland Airport?

    The travel and health documents you'll need for your trip to Portland Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Portland Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Cleveland to Portland, Maine?

Best airlines flying from Cleveland to Portland, Maine

Compare and see reviews for airlines that fly from Cleveland to Portland, Maine with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $216Free CancellationRating
7.9
8,007 reviews
Search Delta flights
United AirlinesPriceFrom $242Free CancellationRating
7.4
9,092 reviews
Search United Airlines flights
American AirlinesPriceFrom $248Free CancellationRating
7.2
11,052 reviews
Search American Airlines flights
SouthwestPriceFrom $256Free CancellationRating
7.9
4,250 reviews
Search Southwest flights

Traveling to a place near Boston?

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

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Cleveland to Portland for you.

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

momondo does allow users to show only those flights to Portland from Cleveland which offer a flexible booking policy as well as other useful filters and features.

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

momondo helps you find the best flight between Cleveland and Portland by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes momondo offers price alerts on flights to Portland from Cleveland. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Portland, Maine trip

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