$50 Cheap flight deals from Sarasota (TPA) to Medford (BOS)

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This Weekend's Flight Deals from Sarasota to Medford

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Aug 1 - Sat, Aug 8
PIE
St. Petersburg-Clearwater Intl.
PSM
Portsmouth Intl.
$382 Roundtrip, found 3 days ago
$382
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Sat, Aug 1 from St. Petersburg-Clearwater Intl. to Portsmouth Intl., returning Sat, Aug 8, priced at $382 found 3 days ago
Sat, Aug 1 - Sat, Aug 8
PIE
St. Petersburg-Clearwater Intl.
PSM
Portsmouth Intl.
$382 Roundtrip, found 3 days ago
$382
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Sat, Aug 1 from St. Petersburg-Clearwater Intl. to Portsmouth Intl., returning Sat, Aug 8, priced at $382 found 3 days ago
Sat, Aug 1 - Sat, Aug 8
PIE
St. Petersburg-Clearwater Intl.
PSM
Portsmouth Intl.
$382 Roundtrip, found 3 days ago
$382
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Sat, Aug 1 from St. Petersburg-Clearwater Intl. to Portsmouth Intl., returning Sat, Aug 8, priced at $382 found 3 days ago
Sat, Aug 1 - Sat, Aug 8
PIE
St. Petersburg-Clearwater Intl.
PSM
Portsmouth Intl.
$382 Roundtrip, found 3 days ago
$382
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Sat, Aug 1 from St. Petersburg-Clearwater Intl. to Portsmouth Intl., returning Sat, Aug 8, priced at $382 found 3 days ago

Airfares from $50 One Way, $96 Round Trip from Sarasota to Medford

Prices starting at $96 for return flights and $50 for one-way flights to Medford were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jan 15 - Fri, Jan 22
SRQ
Sarasota
BOS
Boston
$96 Roundtrip, just found
$96
Roundtrip
just found
Select Allegiant Air flight, departing Fri, Jan 15 from Sarasota to Boston, returning Fri, Jan 22, priced at $96 just found
Fri, Oct 30 - Sat, Nov 7
PGD
Punta Gorda
PSM
Portsmouth
$98 Roundtrip, found 18 hours ago
$98
Roundtrip
found 18 hours ago
Select Allegiant Air flight, departing Fri, Oct 30 from Punta Gorda to Portsmouth, returning Sat, Nov 7, priced at $98 found 18 hours ago
Tue, Sep 1 - Sat, Sep 5
TPA
Tampa
BOS
Boston
$202 Roundtrip, found 5 hours ago
$202
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Sep 1 from Tampa to Boston, returning Sat, Sep 5, priced at $202 found 5 hours ago
Tue, Sep 1 - Tue, Sep 8
TPA
Tampa
BOS
Boston
$219 Roundtrip, found 10 hours ago
$219
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Tue, Sep 1 from Tampa to Boston, returning Tue, Sep 8, priced at $219 found 10 hours ago
Tue, Sep 1 - Tue, Sep 8
TPA
Tampa
BOS
Boston
$219 Roundtrip, found 10 hours ago
$219
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Sep 1 from Tampa to Boston, returning Tue, Sep 8, priced at $219 found 10 hours ago

Medford economy flight packages

Price found within the past 48 hours. Click for updated prices.
Luxury Apartments by Hyatus at Boston Everett
5.0-star property

Luxury Apartments by Hyatus at Boston Everett

9.2/10 Wonderful! (5 reviews)

Sep 18 - Sep 20

2 night stay

Tampa (TPA) to Boston (BOS)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,055, price is now $685 per person
$685
per person
found 1 day ago
We were in Boston for the Mammoth March in Hingham and needed a base for some sight seeing in Boston for the week. We did not have a rental car but the parking garage was easily accessible and secure. We were able to get ubers very easily from the location. The Chelsea train station was only a 5 min walk away and the trains were reliable and efficient. The support staff replied to all our messages in the chat option quickly and were very helpful. The kitchen was well stocked and set up. The apartment was clean and all the linens and towels were freshly laundred. Would recommend this place without hesitation.

Reviewed on Jun 15, 2026

Iris Hotel Boston
4.0-star property

Iris Hotel Boston

9.4/10 Exceptional! (603 reviews)

Sep 12 - Sep 19

7 night stay

Sarasota (SRQ) to Boston (BOS)

Delta • Non-stop • Coach

Boston (BOS) to Sarasota (SRQ)

JetBlue Airways • Non-stop • Coach
Save 100% on your flight
Price was $1,966, price is now $1,205 per person
$1,205
per person
found 1 day ago
Great experience, rooms were clean and very nice. Our expectations were definitely exceeded. The hotel staff was also amazing, the girl at the valet counter was very helpful and so was Alexis at the front desk. Highly recommend. Hotel is centrally located with tons of food options and walking distance to train station.

Reviewed on Jul 27, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,001 reviews)

Sep 3 - Sep 6

3 night stay

St. Petersburg (PIE) to Boston (BOS)

Delta • Coach

Boston (BOS) to St. Petersburg (PIE)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,800, price is now $1,169 per person
$1,169
per person
found 1 day ago
Very nice hotel everything was great very good hospitality!

Reviewed on Jul 27, 2026

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More About Flying To Medford from Sarasota

Route Information for Flights from Sarasota to Medford

Origin Airport IATA Code
TPA
Destination Airport IATA Code
BOS
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Sarasota to Medford

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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.