Cheap Flights to Hillsborough County from $29

View $29 flight on Sun, Jan 18, 2026Opens in a new window

Popular airlines to Hillsborough County

  • American Airlines

    American Airlines

  • Delta

    Delta

  • United

    United

  • JetBlue Airways

    JetBlue Airways

  • Southwest Airlines

    Southwest Airlines

  • Spirit Airlines

    Spirit Airlines

  • Frontier Airlines

    Frontier Airlines

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How much is the cheapest flight to Hillsborough County?

Prices were available within the past 7 days and start at $29 for one-way flights and $58 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Jan 15 - Sun, Jan 18
MCO
Orlando
BOS
Boston
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Jan 15 from Orlando to Boston, returning Sun, Jan 18, priced at $58 just found
Frontier Airlines
Sat, Jan 17 - Tue, Jan 27
MCO
Orlando
BOS
Boston
$59 Roundtrip, found 19 hours ago
$59
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, Jan 17 from Orlando to Boston, returning Tue, Jan 27, priced at $59 found 19 hours ago
Spirit Airlines
Thu, Jan 22 - Sun, Jan 25
MCO
Orlando
BOS
Boston
$61 Roundtrip, just found
$61
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Jan 22 from Orlando to Boston, returning Sun, Jan 25, priced at $61 just found
Frontier Airlines
Sat, Jan 17 - Tue, Jan 20
MCO
Orlando
BOS
Boston
$61 Roundtrip, just found
$61
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jan 17 from Orlando to Boston, returning Tue, Jan 20, priced at $61 just found
Frontier Airlines
Sun, Jan 18 - Mon, Jan 26
MCO
Orlando
BOS
Boston
$64 Roundtrip, found 1 day ago
$64
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Jan 18 from Orlando to Boston, returning Mon, Jan 26, priced at $64 found 1 day ago
Frontier Airlines
Sun, Feb 15 - Wed, Feb 25
MCO
Orlando
BOS
Boston
$65 Roundtrip, found 19 hours ago
$65
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sun, Feb 15 from Orlando to Boston, returning Wed, Feb 25, priced at $65 found 19 hours ago
Frontier Airlines
Thu, Feb 12 - Thu, Feb 19
MCO
Orlando
BOS
Boston
$70 Roundtrip, found 1 hour ago
$70
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Feb 12 from Orlando to Boston, returning Thu, Feb 19, priced at $70 found 1 hour ago
Breeze Airways
Thu, Jan 22 - Sun, Jan 25
MCO
Orlando
PSM
Portsmouth
$75 Roundtrip, found 2 days ago
$75
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jan 22 from Orlando to Portsmouth, returning Sun, Jan 25, priced at $75 found 2 days ago
JetBlue Airways
Thu, Jan 22 - Sun, Jan 25
MCO
Orlando
ORH
Worcester
$123 Roundtrip, found 1 day ago
$123
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Jan 22 from Orlando to Worcester, returning Sun, Jan 25, priced at $123 found 1 day ago
Delta
Sat, Jan 17 - Tue, Jan 20
MCO
Orlando
BOS
Boston
$137 Roundtrip, just found
$137
Roundtrip
just found
Select Delta flight, departing Sat, Jan 17 from Orlando to Boston, returning Tue, Jan 20, priced at $137 just found

Airports in Hillsborough County

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Logan Intl. BOS. Cheapest option available. Flights from $348
BOS
Logan Intl.
Cheapest
Flights from $348
Select flight to Manchester-Boston Regional MHT. Flights from $447
MHT
Manchester-Boston Regional
Flights from $447
Select flight to Worcester Regional ORH. Flights from $685
ORH
Worcester Regional
Flights from $685

Enjoy extra legroom, flight flexibility, and a seamless travel experience.

Hillsborough County Flights Information

Airlines serving
Frontier Airlines, Spirit Airlines, Breeze Airways, JetBlue Airways, Delta
Roundtrip price
from $58

Trending flights to Hillsborough County

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Jan 15 - Sun, Jan 18
MCO
Orlando
BOS
Boston
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Jan 15 from Orlando to Boston, returning Sun, Jan 18, priced at $58 just found
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