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Kissimmee

Cheap flights from Portland, ME (PWM) to Kissimmee, FL

PWM — MCO
Nov 23 — Nov 301
Mon 11/23
Mon 11/30
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Kissimmee are usually found in January or September, booked 82 days in advance, depart on a Tuesday or Wednesday and return on a Sunday

Find flight deals from Portland to Kissimmee

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

February

Cheapest in

January

Average price

$331
Provider with most accurate pricing for Portland-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Portland-Orlando (ORL) flights.
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Highest demand for flights based on searches. 1% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Cheapflights Insights

Everything you need to know about your flight from Portland to Kissimmee

What is the cheapest time of day to fly from PWM to K1S?

Unlike in the morning, when flights are generally more expensive, you can save up to 57% on flights from Portland, Maine to Kissimmee by exploring options for tickets in the evening.

Reviews of airlines servicing Kissimmee

See what other customers who have flown with Breeze Airways,Southwest, andDelta from Portland to Kissimmee have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.2
Very good
326 reviews

Comfort

8.2

Overall

8.2

Crew

8.8

Entertainment

6.8

Food

6.7

Boarding

8.4

Reviews

1 / 19
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.
Breeze Airways
8.2
Very good
326 reviews
Breeze Airways
8.2
Very good
326 reviews

Comfort

8.2

Overall

8.2

Crew

8.8

Entertainment

6.8

Food

6.7

Boarding

8.4

Reviews

1 / 19
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.
Southwest
7.9
Good
4,223 reviews
Breeze Airways
8.2
Very good
326 reviews

Comfort

8.2

Overall

8.2

Crew

8.8

Entertainment

6.8

Food

6.7

Boarding

8.4

Reviews

1 / 19
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.
Delta
7.8
Good
8,679 reviews
Breeze Airways
8.2
Very good
326 reviews

Comfort

8.2

Overall

8.2

Crew

8.8

Entertainment

6.8

Food

6.7

Boarding

8.4

Reviews

1 / 19
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.
JetBlue
7.1
Good
3,067 reviews
Breeze Airways
8.2
Very good
326 reviews

Comfort

8.2

Overall

8.2

Crew

8.8

Entertainment

6.8

Food

6.7

Boarding

8.4

Reviews

1 / 19
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.
American Airlines
7.0
Good
12,193 reviews
Breeze Airways
8.2
Very good
326 reviews

Comfort

8.2

Overall

8.2

Crew

8.8

Entertainment

6.8

Food

6.7

Boarding

8.4

Reviews

1 / 19
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.

Related info for your journey

  • What airport do you fly from for flights from Portland to Kissimmee?

    Portland (PWM) is the airport you will fly out of if you book a flight from Portland to Kissimmee. You should not have trouble finding flights to Kissimmee from Portland; the airport handles an average of 0 outbound flights to Kissimmee per day. You should also have plenty of airline options to choose from since 6 airlines have flights from the Portland airport to Kissimmee. It is only a 2.9 mi journey to Portland (PWM) from Portland’s city center.

  • What are the cheapest airlines to fly from Portland, Maine to Kissimmee one-way?

    The cheapest airline one-way is Breeze Airways, with whom users have recently found tickets for as low as $88. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Portland, Maine to Kissimmee for a low price.

  • What are the cheapest flights from Portland, Maine to Kissimmee?

    Looking for the cheapest flight from Portland, Maine to Kissimmee? While on average our users pay $260, our data indicates the cheapest price to be $126. The most popular route (Portland - Orlando), is priced around $169.

  • Can I find deals for flights from Portland to Kissimmee that include hotel bookings?

    Yes. In addition to deals on Portland to Kissimmee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Kissimmee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Kissimmee.

  • Can I find deals for business class flights from Portland to Kissimmee?

    Yes. Cheapflights offers flight deals from Portland to Kissimmee by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Top 7 airlines flying from Portland to Kissimmee

AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$103Average$275FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$118Average$349FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$121Average$297FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$153Average$471FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$187Average$413FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$199Average$444FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$216Average$421FlexibilityNo cancel feeOn-time69%

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