$243 Cheap flights to Province of Siena

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Top places to visit in Province of Siena

A historic town with tightly packed buildings, a prominent tower, and a church.

Siena

A historic tower with arches and a bell, surrounded by traditional buildings with tiled roofs and satellite dishes.

Montalcino

A historic square with a prominent tower and statues.

Pienza

Cheap flights to Province of Siena from $243 One Way, $155 Round Trip

$155 return flights and $243 one-way flights to Province of Siena were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Jan 18 - Thu, Feb 4

JFK

New York

FLR

Florence

$480

Roundtrip

found 22 hours ago

Sat, Nov 14 - Mon, Nov 23

LAX

Los Angeles

FLR

Florence

$572

Roundtrip

found 12 hours ago

Tue, Apr 6 - Tue, Apr 13

BOS

Boston

FLR

Florence

$591

Roundtrip

just found

Sun, Jan 17 - Fri, Jan 22

EWR

New York

FLR

Florence

$605

Roundtrip

found 4 days ago

Sat, Apr 10 - Sat, Apr 17

EWR

New York

PSA

Pisa

$668

Roundtrip

found 5 days ago

Thu, Apr 8 - Mon, Apr 12

ORD

Chicago

FLR

Florence

$697

Roundtrip

found 6 hours ago

Fri, Aug 20 - Sat, Sep 4

JFK

New York

PSA

Pisa

$700

Roundtrip

found 4 days ago

Deals For This Weekend's Flights

Origin	Destination	Travel Dates	Flights From*
BCN	Florence	November 7 to November 10	$155
LGW	Pisa	November 8 to November 11	$157
FCO	Florence	November 7 to November 14	$166
LCY	Florence	November 6 to November 8	$235
CDG	Florence	November 7 to November 11	$237
JFK	Florence	November 6 to November 13	$878

*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Province of Siena Accommodation Deals

Il Chiostro del Carmine

Via Della Diana 4 Siena SI

$107 nightly

$122 total

Nov 5 - Nov 6

Total with taxes and fees

Stay at this B&B in Siena. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Piazza ...

8.6/10 Excellent! (963 reviews)

"The location was excellent, within walking distance to all the sights but far enough that it was quiet. Breakfast was excellent and if you can get window seating, it will make a perfect start of the day. The staff was helpful but remains in the background unless you need something. The room was clean, ..."

Reviewed on Nov 3, 2026

La Perla

Via Delle Terme 25 Siena SI

Fully refundableReserve now, pay when you stay

$70 nightly

$81 total

Dec 1 - Dec 2

Total with taxes and fees

Stay at this hotel in Siena. Enjoy free WiFi, daily housekeeping, and pillowtop beds. Popular attractions Piazza del Campo and Teatro dei Rozzi are located ...

Sangallo Park Hotel

Strada Di Vico Alto 2 Siena SI

Fully refundableReserve now, pay when you stay

$83 nightly

$94 total

Nov 15 - Nov 16

Total with taxes and fees

Book a stay at this business-friendly hotel in Siena. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Piazza del Campo and Palasport Mens ...

9/10 Wonderful! (622 reviews)

"Excellent staff"

Reviewed on Oct 14, 2026

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Hotel Italia

Viale Camillo Benso Conte di Cavour, 67 Siena SI

Fully refundableReserve now, pay when you stay

$69 nightly

$79 total

Nov 22 - Nov 23

Total with taxes and fees

Stay at this hotel in Siena. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. ...

9.2/10 Wonderful! (1,000 reviews)

"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the ..."

Reviewed on Oct 21, 2026

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.

Our Top Province of Siena Apartment Hotels

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Montepulciano Siena

Stay at this vacation home in Montepulciano. Enjoy a garden, laundry facilities, and patios. Popular attractions Medici Fortress and Torre del Pulcinella are ...

9.6/10 Exceptional! (95 reviews)

"The views were INCREDIBLE! The house was nice and we liked the ability to use the second door to enter upstairs with the luggage. It is so close to the city plaza with a short walk. The parking made it very convenient for us but the views off the huge terrace was simple amazing to wake to every morning. ..."

Reviewed on Oct 23, 2026

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VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.

San Gimignano

Book a stay at this family-friendly villa in San Gimignano. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Fonti Medievali and Archaeological ...

10/10 Exceptional! (124 reviews)

"Thank you so much to our hosts at Villa Iris. They were so welcoming and helpful. The Villa is stunning and our group of 8 people loved staying there for a week and exploring the beautiful Tuscan towns. I highly recommend booking this gorgeous property when planning a vacation to this area. Thanks ..."

Reviewed on Oct 23, 2026

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Chiusarella Arceno Rentals Club Chianti Villa exclusive Pool Concierge freeWiFi

CASTELNUOVO BERARDENGA Tuscany

Book a stay at this family-friendly villa in Castelnuovo Berardenga. Enjoy free WiFi, private pools, and a fitness center. Popular attractions San Felice Winery ...

10/10 Exceptional! (35 reviews)

"Such a beautiful home in a perfect setting, we immediately felt at home. The daily cleaning service was wonderful and friendly. We loved arriving to a fully stocked kitchen, with enough to make a great meal and several snacks throughout our time. I would highly recommend this home!"

Reviewed on Jul 8, 2026

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Save an average of 15% on thousands of hotels when you're signed in

Farmhouse in the heart of the real chiantishire

Castellina in Chianti Tuscany

Stay at this vacation home in Castellina in Chianti. Enjoy a garden, laundry facilities, and patios. Popular attractions Castellina Fortress and Archaeological ...

10/10 Exceptional! (159 reviews)

"Sehr schöne Zeit in dem Farmhaus verbracht.Es ist Alles da was man braucht, wunderschöne Lage ,gutAusgangspunkt um die Chianti erkunden"

Reviewed on Sep 28, 2026

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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.

Score Epic Province of Siena Accommodation Deals

Hotel Athena

P Mascagni 55 Siena SI

Fully refundableReserve now, pay when you stay

$92 nightly

$104 total

Nov 29 - Nov 30

Total with taxes and fees

Book a stay at this business-friendly hotel in Siena. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the breakfast and the helpful staff ...

9.2/10 Wonderful! (1,006 reviews)

"This is a lovely hotel. The front desk staff were very friendly and helpful. Breakfast and dinner were great as was the hospitality shown by the dining room staff. The room was comfortable and clean. The rooftop terrace is an amazing place to enjoy beautiful views and the sunset. I would highly recommend ..."

Reviewed on Nov 4, 2026

Precise Tale Poggio Alla Sala

Via Di Poggio Alla Sala, 10 Montepulciano SI

Book a stay at this luxury hotel in Montepulciano. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...

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Hotel Minerva

Via Garibaldi, 72 Siena SI

Fully refundableReserve now, pay when you stay

$86 nightly

$98 total

Nov 8 - Nov 9

Total with taxes and fees

Book a stay at this family-friendly hotel in Siena. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff in our reviews. Popular ...

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Grand Hotel Continental Siena – Starhotels Collezione

Banchi Di Sopra 85 Siena SI

Fully refundableReserve now, pay when you stay

$285 nightly

$320 total

Dec 4 - Dec 5

Total with taxes and fees

Book a stay at this luxury hotel in Siena. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...

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.

Family Friendly Hotels in Province of Siena

Piazza Paradiso Accomodation

Via di Stalloreggi, 38 Siena SI

$62 nightly

$73 total

Nov 30 - Dec 1

Total with taxes and fees

Book a stay at this luxury affittacamere in Siena. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Piazza del Campo and Pinacoteca ...

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.

San Gimignano

Book a stay at this family-friendly villa in San Gimignano. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Fonti Medievali and Archaeological ...

10/10 Exceptional! (124 reviews)

Families like: Private pool, kitchen, playground, game room

Travelers say...

Reviewed on Oct 23, 2026

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Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

$112 nightly

$128 total

Nov 16 - Nov 17

Total with taxes and fees

Stay at this hotel in Montepulciano. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Civic Museum and Palazzo Ricci are located ...

9.4/10 Exceptional! (220 reviews)

"It was wonderful to spot Bree days in ancient town Montepulciano with Robert family. A Tuscany family,a Tuscany charm, and lots of pleasant Tuscany memories! Arrivederci!"

Reviewed on Nov 3, 2026

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La Terrazza Sul Campo Rooming House

Via di Città 65 Siena SI

Stay at this residence in Siena. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Piazza del Campo and Palazzo Chigi-Saracini are located ...

9.8/10 Exceptional! (256 reviews)

"We loved our overnight stay in Siena. Our room was perfect for our needs and our host was gracious and very helpful. Location was excellent and we hope to stay again. ❤️"

Reviewed on Oct 29, 2026

Get rates

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

Compact

Ford Focus

4 people

Midsize

Toyota Corolla

5 people

SUV

Jeep Compass

5 people

Province of Siena

Why search for low cost fares on your flights to Province of Siena when Orbitz offers the guaranteed lowest prices on foreign and domestic flights? When you travel with Orbitz you can benefit from:

Bargain Flights to Province of Siena

Orbitz offers massive discounts and substantial last-minute savings on your Province of Siena flights. Orbitz ensures that you can find, plan and reserve your flights any destination with ease, all while enjoying the guaranteed lowest prices available anywhere.

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Outstanding Customer Service

Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Province of Siena but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.

Frequently asked questions

Which airlines fly to Province of Siena?

Book a fare with one of the 16 airlines that operate services to Fiumicino - Leonardo da Vinci Intl. Airport (FCO) and get set for awesome new adventures. This popular airport is the jumping-off point for exploring Province of Siena. When you're ready to cross off this region, these international airlines will take you there:

ITA Airways - 666 flights to Province of Siena per month
Ryanair - 423 flights to Province of Siena per month
Vueling - 286 flights to Province of Siena per month

How much is a flight to Province of Siena?

Prices for return flights to Province of Siena this past week ranged from $155 to $878. If you were flying one-way out of Chicago (ORD), you could have landed fares from just $243.

How to book the cheapest flight to Province of Siena?

Picking up cheap flights to Province of Siena is as easy as booking with Orbitz. But if you're eager to make sure you're nabbing the best flight deals around, here are some tips to follow:

Depending on where you're coming from, select the 'Nearby airports' function (located under the departure and arrival form fields). On occasion, alternative departure points will have cheaper fares.
Similarly, click on the 'Show flexible dates' option to bring up the prices for days around your chosen departure. It's possible to find cheaper flight deals if your travel plans are flexible.
To refine your results, hit 'Show options.' You can search based on airlines, seating class, and nonstop and refundable flights. You can also choose your preferred departure and arrival times under 'Sort & Filter' to the left.
Once you've worked out your travel dates, don't delay booking. Airfares normally climb as the departure date gets closer.
Think about combining your hotels, flights and car rental into a package deal with Orbitz to make your budget go even further.
Don't travel during the busy season if possible. By avoiding school vacations and summer, you can make superb savings on your airfare.

What is the best time to book a flight to Province of Siena?

Book your tickets to Province of Siena in January. This is the best time of the year for bargain fares, closely followed by February and August. Catch cheap flights and let your dream vacation come true with Orbitz.

What day of the week is the cheapest to book a flight to Province of Siena?

If you're after inexpensive fares to Province of Siena, the best days of the week to make a booking are Tuesdays, Wednesdays and Saturdays. With Orbitz (and a bit of good timing!), an unbeatable flight deal will be all yours.

What is the cheapest day of the week to fly to Province of Siena?

Look into flying early in the week to nab cheap flights to Province of Siena. Orbitz data from 2020 indicates Monday is generally the cheapest day to head off, followed by Tuesday. Saturday was found to have the highest ticket fares. This is probably because most passengers choose to start their trip when the weekend rolls around.

What is the cheapest month to fly to Province of Siena?

If you have some flexibility with your travel plans, think about jetting off in August. Orbitz data has found that this is generally the best month to take off if you want cheap flights to Province of Siena. As you would imagine, airfares get pricier in the busy month of June and flights book out quickly.

Which airlines allow free cancellation?

Flexibility is important, that's why Orbitz lets you search for fares that won't slap on fees for amendments to your reservation. Fill out your departure and arrival points, then select "Filter by flexible change policies." We'll show you options that include free cancellation within 24 hours of booking and no change fees.

What do I need for the flight to Province of Siena?

Any lengthy flight can be daunting, but it's nothing a little preparation can't solve. We've put together our top tips to make sure your trip flows without a hitch:

Nothing is more important than having your travel documents. Which to bring and how many depend on whether you're flying domestic or international. Be sure to check with your airline. In both cases, you'll need to show some sort of government-issued ID.
If you're flying direct to Province of Siena, chances are you're going to be in the sky for quite some time. Take lots of snacks and entertainment to keep you occupied. Now is a fantastic time to pick up that novel you haven't read yet!
Long-haul voyages can get very cold, especially if you're flying overnight. If you prefer not to stay awake shivering for the length of your journey, bring a sweater and some wool socks.

How do I get cheap first-class/business deals to Province of Siena?

There are ways of booking business or first-class tickets to Province of Siena that won't burn through your wallet. Snap up a seat at the front of the plane for less with these great tips:

Flexibility is key. By being open to different travel dates, you'll have better odds of landing a great deal on first or business-class airfares.
Low-cost airlines offer business-class seats at a fraction of the usual cost. Ditch the full-service carriers and go with one of these cheaper options.
Bid for an upgrade. Some carriers hold online auctions that let you offer a price for a seat at the front of the plane. You may also be able to upgrade with points earned through a loyalty program.

What is the best time to go to Province of Siena?

Province of Siena is a fun getaway destination year-round, but the most popular months to visit are April, May and June. If you prefer warm weather, consider traveling in the summertime. Like most destinations in the Northern Hemisphere, the summer season starts June 20. During this time, temperatures generally hover between 60 ºF and 85 ºF during the daytime.

More to Explore

Siena Vacations

Things to do in Siena

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.