Chiasso Vacations from $999

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Your Chiasso Vacation

From its cosmopolitan vibe to its cultural experiences and spectacular views, you'll find loads of reasons to spend time in the mountainous city of Chiasso. Discover these highlights and more when you lock in your vacation package to Chiasso. Eager to explore your new surroundings? Como Cathedral, Villa Olmo and Volta Temple are among the leading places to visit during a trip to Chiasso. Expedia has what you need to escape your routine. Tailor your vacation to Chiasso to match your travel style, whatever that may be.

The Latest Chiasso vacation packages

Price found within the past 48 hours. Click for updated prices.
Grand Visconti Palace

Grand Visconti Palace

4 out of 5
Porta Lodovica
Save 100% on your flight
Price was $1,475, price is now $999 per person
$999
per person
Mar 9 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Milan (LIN)
8.8/10 Excellent! (1,000 reviews)
Nice ppl, parking is the not the easiest! Maybe they should hire valet

Reviewed on Jan 5, 2026

NEMI Hotel

NEMI Hotel

5 out of 5
Porta Vittoria
Save 100% on your flight
Price was $1,919, price is now $1,255 per person
$1,255
per person
Mar 9 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Milan (LIN)
9.6/10 Exceptional! (13 reviews)
What a wonderful hotel, so glad my research led me to it!! I am very picky with hotels and am only happy in new luxury hotels and this hotel was fabulous! Even the air conditioning was wonderful and I almost never can say that!! Perfect hotel, will only stay here when I return to Milan from now on. Area around hotel is good too, with dining, shopping and gelato options you won’t be disappointed!

Reviewed on Sep 21, 2025

Uptown Palace

Uptown Palace

4 out of 5
Milan Centre
Save 100% on your flight
Price was $1,919, price is now $1,276 per person
$1,276
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Milan (LIN)
8.6/10 Excellent! (1,001 reviews)
Rooms were clean and the shower was awesome. Decent distance from the duomo but very far from milan centrale station. Cant fault the hotel. Really good location

Reviewed on Jan 25, 2026

Magna Pars- L'Hotel à Parfum Small Luxury Hotels of the World

Magna Pars- L'Hotel à Parfum Small Luxury Hotels of the World

5 out of 5
Porta Genova
Price was $1,795, price is now $1,263 per person
$1,263
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Milan (LIN)
9.4/10 Exceptional! (460 reviews)
I absolutely loved my stay in Milan at Magna Pars. It is one of those places that makes feel at home. Each suite has their unique scent, inspired by their perfumes. All staff are incredibly friendly, welcoming, polite and a pleasure to work with. I still miss my time there, even days after my trip ended, and I’m very much looking forward to returning one day.

Reviewed on Jan 13, 2026

Palazzo Cordusio Gran Meliá – The Leading Hotels of the World

Palazzo Cordusio Gran Meliá – The Leading Hotels of the World

5 out of 5
Milan Centre
Save 100% on your flight
Price was $3,049, price is now $2,210 per person
$2,210
per person
Feb 26 - Mar 1
found 24 hours ago
Roundtrip flight included
New York (JFK) to Milan (LIN)
9.4/10 Exceptional! (43 reviews)
Welcoming staff who anticipate your needs and always helpful. Amazing terrace area

Reviewed on Nov 10, 2025

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Chiasso Hotel Deals

Hotel Osteria della Pista

Hotel Osteria della Pista

4 out of 5
Via Verbano 1 Casorate Sempione VA
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $104 total per night from Jan 31 to Feb 1
$104 total
Jan 31 - Feb 1
Total with taxes and fees
9.4/10 Exceptional! (1,236 reviews)
Great staff, location and value

Reviewed on Jan 21, 2026

Hotel Osteria della Pista
Crowne Plaza Milan - Malpensa Airport by IHG

Crowne Plaza Milan - Malpensa Airport by IHG

4 out of 5
Via Arturo Ferrarin, 7 Somma Lombardo VA
Fully refundable
$119 nightly
The price is $136 total per night from Feb 25 to Feb 26
$136 total
Feb 25 - Feb 26
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
Clean room. Good wifi

Reviewed on Jan 23, 2026

Crowne Plaza Milan - Malpensa Airport by IHG
Palace Hotel

Palace Hotel

4 out of 5
Lungo Lario Trieste, 16 Como CO
Fully refundableReserve now, pay when you stay
$220 nightly
The price is $254 total per night from Jan 28 to Jan 29
$254 total
Jan 28 - Jan 29
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
Everything was awesome the view from the lake view room was incredible

Reviewed on Jan 19, 2026

Palace Hotel
See all 7,547 properties in Chiasso
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.

Find the Best Chiasso Vacation Packages

Chiasso Essential Information

Language
French
Currency
Swiss francs
Local Welcome
Salut / Bonjour
Local Goodbye
Au revoir / À bientôt
Population
8,100
Max Temp Winter
45ºF
Max Temp Summer
75ºF
Top Sights
Cinema Theatre Chiasso, Museum dArt and Mount San Giorgio

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Frequently asked questions

How much does a Chiasso vacation package cost?
Offering great value package deals from $999 on Expedia, you'll be thrilled with how little a vacation to Chiasso costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Chiasso?
You're likely to find lower prices and greater availability in January, March and November. Browse our cheap Chiasso vacation packages and you could get some great off-season discounts.
How many days is enough for Chiasso?
The ideal duration for your Chiasso vacation depends on what you'd like to see. Typically, a handful of days to a week will give you enough time to visit all the major sights and explore some hidden spots along the way.
Is it worth booking a vacation package to Chiasso?
Well known for its walking trails, culture and plenty of other highlights, you can be certain Chiasso is a good vacation destination. Some of the top attractions to put on your to-do list? Visit Cinema Theatre Chiasso and Via Gottardo during your Chiasso vacation.
How to find the best Chiasso package deals?
Finding a cheap Chiasso package deal is a cinch with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, add some filters and browse what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Chiasso package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Chiasso vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and hotels separately. Better still, you can personalize your Chiasso escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Chiasso?
Score incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Chiasso adventure.
Does Expedia offer Book Now, Pay Later Chiasso vacation packages?
If you're anything like us, you love exploring new places but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Chiasso trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.