Cheap Flights to Hillsborough County from $44 (2026/2027)

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Jet to one of Hillsborough County's top cities

A city street with historic buildings, a modern skyscraper, and parked cars.

Manchester

Flights
Manchester

How Much Does it Cost To Fly To Hillsborough County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Jan 21 - Sat, Jan 30
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Thu, Jan 21 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Sat, Jan 30, priced at $112 found 1 day ago
Sun, Apr 18 - Fri, Apr 30
PIE
St. Petersburg-Clearwater Intl.
PSM
Portsmouth Intl.
$132 Roundtrip, found 3 days ago
$132
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Sun, Apr 18 from St. Petersburg-Clearwater Intl. to Portsmouth Intl., returning Fri, Apr 30, priced at $132 found 3 days ago
Thu, Dec 3 - Sun, Dec 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Sun, Dec 6, priced at $137 found 1 day ago
Wed, Dec 9 - Wed, Dec 16
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Dec 9 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Dec 16, priced at $138 found 1 day ago
Thu, Dec 3 - Mon, Dec 7
MCO
Orlando Intl.
BOS
Logan Intl.
$150 Roundtrip, found 15 hours ago
$150
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Orlando Intl. to Logan Intl., returning Mon, Dec 7, priced at $150 found 15 hours ago
Tue, Nov 10 - Wed, Nov 18
MCO
Orlando Intl.
BOS
Logan Intl.
$159 Roundtrip, found 9 hours ago
$159
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Nov 10 from Orlando Intl. to Logan Intl., returning Wed, Nov 18, priced at $159 found 9 hours ago
Tue, Nov 10 - Wed, Nov 18
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$159 Roundtrip, found 11 hours ago
$159
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Tue, Nov 10 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Wed, Nov 18, priced at $159 found 11 hours ago
Sat, Nov 14 - Sat, Nov 14
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$173 Roundtrip, found 21 hours ago
$173
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Sat, Nov 14 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Sat, Nov 14, priced at $173 found 21 hours ago
Tue, Nov 10 - Wed, Nov 18
MCO
Orlando Intl.
BOS
Logan Intl.
$179 Roundtrip, found 9 hours ago
$179
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Tue, Nov 10 from Orlando Intl. to Logan Intl., returning Wed, Nov 18, priced at $179 found 9 hours ago
OriginDestinationTravel DatesFlights From*
BWIBostonNovember 17 to January 11$117
BWILondonderryNovember 10 to November 13$171
BWIWorcesterNovember 7 to November 13$593
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
BWIBostonOctober 25 to October 28$358
BWILondonderryOctober 24 to October 25$495
BWIWorcesterOctober 23 to October 25$748
*Prices include taxes and fees

Best Hillsborough County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront
4.5-star property

Battery Wharf Hotel, Boston Waterfront

Dec 4 - Dec 7

3 night stay

Chicago (CHI) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
Price was $879, price is now $512 per person
$512
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Dec 4 - Dec 7

3 night stay

Chicago (CHI) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,499, price is now $874 per person
$874
per person
found 1 day ago
Four Seasons Hotel Boston
5.0-star property

Four Seasons Hotel Boston

Dec 22 - Dec 28

6 night stay

Los Angeles (LAX) to Boston (BOS)

JetBlue Airways • Coach

Boston (BOS) to Los Angeles (LAX)

Southwest Airlines • Coach
Save 100% on your flight
Price was $3,345, price is now $2,076 per person
$2,076
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Chicago to Hillsborough County
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Travelers ❤️ These Hillsborough County 🏨

Comfort Inn Manchester Airport

Comfort Inn Manchester Airport

2.5 out of 5
298 Queen City Ave Manchester NH
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Southern New Hampshire University Arena and Northeast Delta Dental Stadium are located nearby.
8.2/10 Very Good! (1,005 reviews)
"It was a good stay. Lots of noise from interstate. Clean room nice staff"

Reviewed on Oct 16, 2026

Opens in a new windowComfort Inn Manchester Airport
Best Western Plus Executive Court Inn & Conference Center

Best Western Plus Executive Court Inn & Conference Center

3 out of 5
13500 S Willow St Manchester NH
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Southern New Hampshire University Arena and New Hampshire Aviation Historical Society are located nearby.
Opens in a new windowBest Western Plus Executive Court Inn & Conference Center
Motel 6 Nashua, NH - South

Motel 6 Nashua, NH - South

2 out of 5
77 Spit Brook Rd Nashua NH
Stay at this motel in Nashua. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Fun World and Pheasant Lane Mall are located nearby.
7.2/10 Good! (1,007 reviews)
"best motel ive stayed at honestly. Despite the noise & ppl. It was clean"

Reviewed on Oct 16, 2026

Opens in a new windowMotel 6 Nashua, NH - South
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Clarion Inn Nashua

Clarion Inn Nashua

2.5 out of 5
10 Saint Laurent Street Nashua NH
Book a stay at this business-friendly hotel in Nashua. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Nashua National Fish Hatchery and Holman Stadium are located nearby.
Opens in a new windowClarion Inn Nashua
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.

Frequently asked questions

How much is the cheapest flight to Hillsborough County?
In the last seven days, the cheapest roundtrip flight to Hillsborough County cost $112 on our site. Search through our awesome deals, secure your booking and look forward to your next exciting getaway. This price was available on Travelocity for flights to Hillsborough County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Hillsborough County?
Grab your luggage and take off with one of the 17 airline companies that operate flights to Hillsborough County. Consider booking with the popular air carrier, American Airlines. It operates approximately 325 flights every month to Manchester, Hillsborough County's major city, so finding the right fare should be a breeze.
What is the cheapest month to fly to Hillsborough County?
If you've been dreaming of a trip to Hillsborough County, January is the cheapest time to jet off. This is according to Travelocity's direct return flight demand between January and December last year. Work out your dates and book your flights today.
How can I check my flight status to Hillsborough County?
Visit the Travelocity customer portal, Trips. You'll find all things related to your flight to Hillsborough County here, including alerts about any gate changes, flight delays and more. You'll locate Trips at the top of the Travelocity homepage. Create your free account and get the answers you need. Or you can look up your itinerary while you're on the move and get real-time notifications through the Travelocity app. All your itineraries are in one convenient place, so you can easily share details with any members of your family flying with you.
How do I find the best deals on flights to Hillsborough County?
Be flexible with your dates and you're likely to find a sensational deal. After you've searched for flights on Travelocity, click the "Flexible dates" box above your results to see all the prices for nearby days. Also try to book ahead of schedule and avoid peak periods. In the last seven days, the lowest price for a return flight to Hillsborough County was $112. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Hillsborough County with Travelocity?
From cheap family flights to activities, rental cars and more, Travelocity is your one-stop shop for epic adventures. With everything at hand, you can relax while daydreaming about the fun things that are waiting for you in Hillsborough County and less time on the nitty-gritty of travel planning. Plus with our Price Match Guarantee and free cancellation on most activities, our goal is to make your next vacation a magical one.
What are the most popular flight routes to Hillsborough County?
To help you choose your flights to Hillsborough County, here's our list of some of the major routes:

  • Philadelphia, PA (PHL-Philadelphia Intl.) to Manchester-Boston Regional Airport (MHT) - 645 flights a month.
  • Charlotte, NC (CLT-Charlotte-Douglas Intl.) to Manchester-Boston Regional Airport (MHT) - 624 flights a month.
  • Washington, DC (IAD-Washington Dulles Intl.) to Manchester-Boston Regional Airport (MHT) - 424 flights a month.

How much is a flight to Hillsborough County on average?
Based on prices found on Travelocity over the last seven days, roundtrip flights to Hillsborough County cost between $112 and $748. When you're ready to take off, Travelocity will help you find a fare to suit your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Hillsborough County?
To get a feel for the average flying time of a direct flight to Hillsborough County, take a look at these common routes:

  • Philadelphia, PA (PHL-Philadelphia Intl.) to Manchester-Boston Regional Airport (MHT) - 1 hour and 27 minutes
  • Charlotte, NC (CLT-Charlotte-Douglas Intl.) to Manchester-Boston Regional Airport (MHT) - 2 hours and 12 minutes
  • Washington, DC (IAD-Washington Dulles Intl.) to Manchester-Boston Regional Airport (MHT) - 1 hour and 41 minutes

What can I expect on a flight to Hillsborough County?
This mostly depends on where you're departing from and which carrier you're jetting off with. Chances are you'll find all sorts of flights to Hillsborough County, from business fares to cheap flights for family vacations. On long-haul flights, your carrier will usually provide entertainment and warm meals as well as games for the youngsters.