Title: $89 Cheap Flights to Winchendon, MA - Expedia.com

![The Millers River in Winchendon, Massachusetts](https://images.trvl-media.com/place/3000441689/ee34b0fc-35dd-4fd4-bfe5-cd47ccc3b39d.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/3000441689/ee34b0fc-35dd-4fd4-bfe5-cd47ccc3b39d.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# $89 Cheap Flights to Winchendon, MA

[View $89 flight on Mon, Jun 15, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:LGA,to:ORH,departure:6/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:88.40&airProductToken=AQo3CjUIxJgBEgQ1NDI0GMsBIK48KJrljwMw3-WPAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTVCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) 

[Winchendon Travel Guide](https://expedia.com/Winchendon.dx3000441689)[Hotels in Winchendon](https://expedia.com/Winchendon-Hotels.d3000441689.Travel-Guide-Hotels)[Car Rentals in Winchendon](https://expedia.com/Car-Rentals-In-Winchendon.d3000441689.Car-Rental-Guide)[Winchendon Vacation Packages](https://expedia.com/Winchendon.d3000441689.Destination-Travel-Guides)

## Popular airlines to Winchendon

- ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg)  
American Airlines  
[](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Winchendon, Massachusetts, United States of America,departure:3/29/2026TANYT&leg2=from:Winchendon, Massachusetts, United States of America,to:CMH,departure:4/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}])
- ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg)  
JetBlue Airways  
[](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Winchendon, Massachusetts, United States of America,departure:3/29/2026TANYT&leg2=from:Winchendon, Massachusetts, United States of America,to:CMH,departure:4/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}])
- ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg)  
Delta  
[](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Winchendon, Massachusetts, United States of America,departure:3/29/2026TANYT&leg2=from:Winchendon, Massachusetts, United States of America,to:CMH,departure:4/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}])
- ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_QR.svg)  
Qatar Airways  
[](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Winchendon, Massachusetts, United States of America,departure:3/29/2026TANYT&leg2=from:Winchendon, Massachusetts, United States of America,to:CMH,departure:4/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"QR"}}])
- ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AD.svg)  
Azul  
[](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Winchendon, Massachusetts, United States of America,departure:3/29/2026TANYT&leg2=from:Winchendon, Massachusetts, United States of America,to:CMH,departure:4/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AD"}}])

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## How much is the cheapest flight to Winchendon?

Prices were available within the past 7 days and start at $89 for one-way flights and $177 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

All deals

One way

Roundtrip

![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif)

Tue, Apr 7 - Fri, Apr 10

LGA

New York

ORH

Worcester

$181

Roundtrip

found 1 day ago

[](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:LGA,to:ORH,departure:4/7/2026TANYT&leg2=from:ORH,to:LGA,departure:4/10/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:180.30&airProductToken=AQo3CjUIxJgBEgQ1NDI0GMsBIK48KMTdiQMwht6JAzhFQABYAWoJTUFJTkJBU0lDcghWRFZTQTBCQwo3CjUIxJgBEgQ1NDI0GK48IMsBKJGAigMw3ICKAzhFQABYAWoJTUFJTkJBU0lDcghWRFZTQTBCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE)

![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif)

Thu, Apr 9 - Sun, Apr 12

FLL

Fort Lauderdale

ORH

Worcester

$183

Roundtrip

found 5 days ago

[](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:FLL,to:ORH,departure:4/9/2026TANYT&leg2=from:ORH,to:FLL,departure:4/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:182.30&airProductToken=AQovCi0IwmwSBDIwMjAY5VogrjwosvOJAzDn9IkDOExAAFgBagJETnIIUEkyUVVFTDEKLwotCMJsEgQyMTE5GK48IOVaKP6WigMwv5iKAzhMQABYAWoCRE5yCFBJMlFVRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ)

![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif)

Wed, Apr 1 - Sat, Apr 4

MCO

Orlando

ORH

Worcester

$188

Roundtrip

found 6 days ago

[](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ORH,departure:4/1/2026TANYT&leg2=from:ORH,to:MCO,departure:4/4/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:187.10&airProductToken=AQpuCjUIxJgBEgQxNTczGMxwIMsBKJiXiQMwu5iJAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTlCQwo1CMSYARIENTQyNBjLASCuPCiEmokDMMaaiQM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0E5QkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB)

![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif)

Wed, Mar 25 - Mon, Mar 30

MCO

Orlando

ORH

Worcester

$193

Roundtrip

found 5 days ago

[](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:ORH,departure:3/25/2026TANYT&leg2=from:ORH,to:MCO,departure:3/30/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:192.10&airProductToken=AQpmCjEIwYIBEgQxNzA2GMxwIO9ZKNDHiAMw68iIAzhCQABYAWoFQkFTSUNyCFFVQUpaU0JWCjEIwYIBEgQ1ODA0GO9ZIK48KP_JiAMwz8qIAzhCQAFYAWoFQkFTSUNyCFFVQUpaU0JWEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw)

![Accessrail](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/9b.gif)

Fri, Jun 5 - Sun, Jun 7

AVT

Aventura

ORH

Worcester

$416

Roundtrip

found 6 days ago

[](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:AVT,to:ORH,departure:6/5/2026TANYT&leg2=from:ORH,to:AVT,departure:6/7/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:415.43&airProductToken=AQpiCjEIuYQBEgQzOTQzGKCdASDlWijQ8o4DMPzyjgM4WUAAWAFqBVNNQVJUcgdZQlJJR0hUCi0IwmwSBDIwMjAY5Vogrjwo6fSOAzCe9o4DOFBAAVgBagJBTnIIUEkyUVVFWTUKYQosCMJsEgM5ODcYrjwgzHAoxIuPAzDyjI8DOFpAAFgBagJBTnIIWkk0QVVFWTUKMQi5hAESBDM4MDcYzHAgoJ0BKNeOjwMwlZCPAzhZQAFYAWoFU01BUlRyB1lCUklHSFQSCggBEAEYASoCQjYYASIECAEQASgCKAMoBDAB)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

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## Frequently asked questions

### What month is the cheapest to fly to Winchendon?

### Which US cities have the cheapest flights to Winchendon?

### Which US cities fly direct to Winchendon?

> - New York
> - Washington
> - Chicago
> - Philadelphia
> - Charlotte

### How to find a cheap flight to Winchendon?

### How to get a cheap last-minute flight to Winchendon?

### How far in advance should I book a flight to Winchendon?

### Which day of the week is the cheapest day to buy a plane ticket to Winchendon?

### Which airlines fly to Winchendon?

> - Delta Air Lines
> - American Airlines
> - United Airlines
> - JetBlue Airways

### Where do you fly into Winchendon?

### How far is the airport from central Winchendon?

### Can I save money by booking a Winchendon trip package?

### Can I change or cancel my flight to Winchendon?

\*Flight schedules are subject to change.

## Book with confidence

# Tips to find the cheapest flights to Winchendon

**The cheapest day to fly**

Get started finding a cheap flight to Winchendon on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

**The cheapest month to fly**

April is the cheapest month to fly to Winchendon. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Winchendon. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute. 

**The most affordable time to book a flight**

Typically, a Sunday can be the cheapest time to book a flight to Winchendon, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation. 

**The cheapest round-trip tickets to Winchendon**

The lowest price for round-trip flights to Winchendon in 2026 starts from from $177, while one-way tickets start from from $89\. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Winchendon. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

**The cheapest airlines flying to Winchendon**

Delta, American Airlines, JetBlue Airways, Accessrail are just some of the airlines that can typically offer cheap tickets to Winchendon. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Winchendon and countless more destinations worldwide.

**The most affordable airports to fly into**

To view the cheapest airports to fly into for Winchendon, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Winchendon. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

**Save with a package**

With Expedia's amazing [package deals](https://www.expedia.com/package-deals), you could save hundreds of dollars by booking your Winchendon plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving. 

**Date flexibility for the cheapest flights to Winchendon**

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Winchendon. 

**Stopover savings**

The cheapest tickets to Winchendon are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Winchendon. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

**Get Expedia's Price Drop Protection**

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference\*. This gives you peace of mind that you're getting one of the cheapest flights to Winchendon for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

\*Terms apply.

**Use our Price Tracking feature**

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Winchendon. Simply download the free Expedia app to your smart device and activate Winchendon flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

**Book with Expedia**

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Winchendon. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. The percentages you see are averages. 

## Travel information

| Destination airport           | Worcester Regional |
| ----------------------------- | ------------------ |
| Destination airport IATA code | ORH                |
| Destination city name         | Worcester          |
| Roundtrip price               | $177               |

## Trending flights to Winchendon

Prices were available within the past 7 days and start at $89 for one-way flights and $177 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

All deals

One way

Roundtrip

![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif)

Wed, Jun 17 - Wed, Jun 17

FLL

Fort Lauderdale

ORH

Worcester

$177

Roundtrip

found 6 days ago

[](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:FLL,to:ORH,departure:6/17/2026TANYT&leg2=from:ORH,to:FLL,departure:6/17/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:176.70&airProductToken=AQovCi0IwmwSBDIwMjAY5Vogrjwot_uPAzDz_I8DOExAAFgBagJETnIIUEkyUVVPTDEKLwotCMJsEgQyMTE5GK48IOVaKKz9jwMw8_6PAzhMQABYAWoCRE5yCFBJMlFVT0wxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ)

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