$69 Cheap flights to Cheshire County

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Top places to visit in Cheshire County

A street with historic buildings, a church steeple, and autumn foliage.
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Keene

Keene

Cheap flights to Cheshire County from $69 One Way, $153 Round Trip

$153 return flights and $69 one-way flights to Cheshire County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Dec 5 - Sat, Dec 12
MCO
Orlando
MHT
Manchester
$153 Roundtrip, found 14 hours ago
$153
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Sat, Dec 5 from Orlando to Manchester, returning Sat, Dec 12, priced at $153 found 14 hours ago
Mon, Feb 1 - Sat, Feb 6
FLL
Fort Lauderdale
MHT
Manchester
$212 Roundtrip, found 2 hours ago
$212
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Mon, Feb 1 from Fort Lauderdale to Manchester, returning Sat, Feb 6, priced at $212 found 2 hours ago
Wed, Dec 2 - Thu, Dec 10
BOS
Boston
MHT
Manchester
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Dec 2 from Boston to Manchester, returning Thu, Dec 10, priced at $249 found 1 day ago
Wed, Dec 2 - Thu, Dec 10
BOS
Boston
MHT
Manchester
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Dec 2 from Boston to Manchester, returning Thu, Dec 10, priced at $249 found 1 day ago
Sat, Jan 16 - Tue, Jan 19
MCO
Orlando
ORH
Worcester
$302 Roundtrip, found 9 hours ago
$302
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Sat, Jan 16 from Orlando to Worcester, returning Tue, Jan 19, priced at $302 found 9 hours ago
Wed, Dec 9 - Wed, Dec 16
MCO
Orlando
MHT
Manchester
$316 Roundtrip, found 17 hours ago
$316
Roundtrip
found 17 hours ago
Select United flight, departing Wed, Dec 9 from Orlando to Manchester, returning Wed, Dec 16, priced at $316 found 17 hours ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
MCOLondonderryOctober 31 to November 11$308
TPALondonderryNovember 1 to November 13$402
RDULondonderryNovember 1 to November 5$408
ATLLondonderryNovember 1 to November 6$593
DCAWorcesterOctober 31 to November 1$617
CLTLondonderryOctober 30 to October 31$619
MCOWorcesterOctober 30 to November 1$710
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Cheshire County Accommodation Deals

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $113 total per night from Nov 3 to Nov 4
$113 total
Nov 3 - Nov 4
Total with taxes and fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Opens in a new windowDays Inn by Wyndham Keene NH
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $154 total per night from Nov 1 to Nov 2
$154 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.2/10 Very Good! (1,000 reviews)
"Breakfast was exceptional. Lori keeps everything clean and organized. We have never been to a hotel breakfast that comes close."

Reviewed on Oct 26, 2026

Opens in a new windowBest Western Plus Keene Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $146 total per night from Nov 1 to Nov 2
$146 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,001 reviews)
"Very clean with friendly staff"

Reviewed on Oct 28, 2026

Opens in a new windowKeene Elm City Hotel, an Ascend Collection Hotel
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Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 out of 5
20 Riverside Drive West Chesterfield NH
Fully refundable
$146 nightly
The price is $158 total per night from Nov 23 to Nov 24
$158 total
Nov 23 - Nov 24
Total with taxes and fees
Book a stay at this business-friendly hotel in West Chesterfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful ...
Opens in a new windowRiverside Hotel, an Ascend Collection Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Cheshire County

Get the absolute lowest prices on flights to Cheshire County by shopping with Orbitz. Orbitz is the most efficient travel planner around, allowing you to search, compare and book discount domestic and international flights fast. With cutting-edge mobile tools and access to frequent flier rewards programs, we have everything you need for both your routine and holiday excursions.

Book Your Flight To Cheshire County Using Your Mobile Device

New mobile app tools enable those with hand-held devices to scout out the best bargains and to secure tickets from any location. If you have an iPhone, iPad or Android device, you may take advantage of special discounts, only available to mobile device customers, when you book hotel rooms or car rentals on the same day as booking Cheshire County flights.

Avoid Check-In Hassles When Traveling On Flights to Cheshire County

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Cheshire County flights. Mobile apps can also be used to share travel itineraries with family members or business associates.

Keeping Everyone Up To Date

When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.

Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Cheshire County flight using Orbitz.

Frequently asked questions

Which airlines fly to Cheshire County?
There are 12 airlines that go to Manchester-Boston Regional Airport (MHT). With this many to select from, there's a great chance you'll find a bargain flight! Your Cheshire County adventure awaits with one of these leading air carriers:

  • American Airlines - 123 flights to Cheshire County per month
  • Southwest Airlines - 96 flights to Cheshire County per month
  • Spirit Airlines - 50 flights to Cheshire County per month

How much is a flight to Cheshire County?
Prices for round-trip flights dropped as low as $153 this week to Cheshire County, and peaked at $710. Passengers flying out of Orlando (MCO) managed to pick up one-way flights starting from just $69.
How to book the cheapest flight to Cheshire County?
With Orbitz, you'll find some of the most amazing flight deals around from a huge range of airlines. But if you'd like to increase your chances of landing cheap flights to Cheshire County, here are some suggestions designed to help:

  • Consider taking off from or landing at other airports to save on your flight. Enter your preferred departure and arrival airports in the form fields, then select the 'Nearby airports' function below. It will list any available options.
  • If your plans aren't set in concrete, click on the 'Show flexible dates' link to view the flight deals for multiple departure dates. If you find a better fare, book it.
  • You can also use the 'Show options' link to filter results for your preferred carrier, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even pick the time of day you'd like to fly.
  • Once you've sorted out your travel dates, don't waste time booking your flight. Ticket prices generally climb as the departure date gets closer.
  • Think about bundling your flights, hotels and car rental into an Orbitz package deal — the more you book, the more you save.
  • Flying during the busy season often means costly airfares. Try to avoid traveling over popular dates, such as school breaks, Thanksgiving and Easter.

What is the best time to book a flight to Cheshire County?
Reserve your flights to Cheshire County in January. This is the ideal time of the year for low prices, closely followed by February and August. Score cheap flights and let your dream vacation come true with Orbitz.
What day of the week is the cheapest to book a flight to Cheshire County?
To land a great flight deal, make a booking on a Tuesday, Wednesday or Saturday. Usually, these are the cheapest days of the week to book seats to Cheshire County.
What is the cheapest day of the week to fly to Cheshire County?
You can nab cheap flights to Cheshire County by hopping on a plane on a Monday, according to Orbitz data from 2020. Tuesday is the next cheapest day, while Saturday has the most expensive ticket prices. Whether you prefer to stretch your travel budget or fly out on any day that's convenient, you'll always get a terrific deal with Orbitz.
What is the cheapest month to fly to Cheshire County?
We won't keep you in suspense — based on Orbitz data, August is generally the most inexpensive month to fly. Perfect for those who want a weekend getaway or just a break from it all before the weather turns. Be aware that the most expensive time to fly is the height of summer, with airfares at their highest in June.
Which airlines allow free cancellation?
Things change, and we think your flight should be able to as well. That's why Orbitz makes it a breeze to search for airlines with free cancellation and no change fees. Simply enter your departure and arrival points and then select "Filter by flexible change policies." Now that's peace of mind!
What do I need for the flight to Cheshire County?
From onboard activities to travel necessities like hand sanitizer, there are some things a seasoned flyer always takes with them. To make sure you're ready for your flight, have a read through this handy list:

  • Travel paperwork such as e-tickets and identification are a must. To avoid any last-minute delays when checking in, ensure that your booking is under the exact name, birth date and gender as indicated on your current ID.
  • Pack your carry-on bag with snacks and activities and you'll easily pass the time on this medium-haul flight. Wherever possible, jump on the airport's Wi-Fi and save your favorite podcast or playlist to your phone or tablet prior to take off.
  • Never mind what the season is, plane cabins can often get quite cool. Bring an extra layer on your journey to stay warm and comfy.

How do I get cheap first-class/business deals to Cheshire County?
Smart travelers have a talent for finding business or first-class airfares to Cheshire County without the eye-watering price tag. Follow in their footsteps with these helpful hints:

  • Being flexible isn't just for the gym. Leave some room to move around your travel dates so you can snap up more affordable airfares when they pop up.
  • Search for a low-cost carrier that offers seats in business class. They usually come with extra space and a glass of bubbly — but without the high price.
  • Make the most of your airline's loyalty scheme and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in an online auction.

What is the best time to go to Cheshire County?
There's no right or wrong time to experience Cheshire County, but February, March and May are the liveliest months. Like most places in the Northern Hemisphere, the summer season starts June 20. If you'd prefer to spend your days in a light T-shirt than a thick winter coat, this time of year would suit you perfectly. Expect average daytime highs of 75 ºF and nighttime lows around 55 ºF.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.