Chiasso Vacations from $1,147

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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.
Uptown Palace

Uptown Palace

4 out of 5
Milan Centre
Price was $1,642, price is now $1,147 per person
$1,147
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Milan (MXP)
8.6/10 Excellent! (1,001 reviews)
Muy limpio y elegante

Reviewed on Jun 4, 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
Save 100% on your flight
Price was $2,465, price is now $1,425 per person
$1,425
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Milan (MXP)
9.4/10 Exceptional! (550 reviews)
Amazing rooftop bar and great restaurant Fantastic breakfast, Interesting location

Reviewed on May 29, 2026

Parco San Marco Lifestyle Beach Resort

Parco San Marco Lifestyle Beach Resort

4 out of 5
Save 100% on your flight
Price was $2,569, price is now $1,655 per person
$1,655
per person
Aug 25 - Aug 30
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to Milan (MXP)
9.6/10 Exceptional! (468 reviews)
The resort itself is absolutely beautiful and the view is amazing but you have a lot of extra add ons such as a fee to use the cups in your room also having a car is very useful transport is hard to come by. The staff is very friendly and helpful!

Reviewed on May 29, 2026

Grand Hotel Victoria Concept & Spa, by R Collection Hotels

Grand Hotel Victoria Concept & Spa, by R Collection Hotels

5 out of 5
Save 100% on your flight
Price was $5,912, price is now $4,028 per person
$4,028
per person
Aug 25 - Aug 30
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to Milan (MXP)
9.8/10 Exceptional! (120 reviews)
Fantastic location, amenities and staff!

Reviewed on Jun 2, 2026

Hotel Promessi Sposi

Hotel Promessi Sposi

4 out of 5
Price was $2,392, price is now $1,744 per person
$1,744
per person
Aug 25 - Aug 30
found 24 hours ago
Roundtrip non-stop flight included
New York (JFK) to Milan (MXP)
9.2/10 Wonderful! (202 reviews)
Room overlooking the Lake was beautiful. Breakfast was fantastic and the bar was top notch. Great location, walking distance into the City Center of Lecco, and a short bus ride away from Bellagio. Great food options nearby as well. Would love to come stay here again.

Reviewed on May 13, 2026

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Chiasso Hotel Deals

Holiday Inn Express Milan - Malpensa Airport by IHG

Holiday Inn Express Milan - Malpensa Airport by IHG

3 out of 5
Via de Pinedo Ang. Somma Lombardo VA
Fully refundable
$106 nightly
The price is $120 total per night from Jun 24 to Jun 25
$120 total
Jun 24 - Jun 25
Total with taxes and fees
8.6/10 Excellent! (1,017 reviews)
"One night stay to catch a morning flight. We were able to check in early which was greatly appreciated. The gentleman at the front desk was wonderful-very helpful, friendly and knowledgeable. All staff we encountered was 5star. Room was very clean and surprisingly quiet considering how close to the ..."

Reviewed on Jun 4, 2026

Holiday Inn Express Milan - Malpensa Airport by IHG
Hotel Funicolare

Hotel Funicolare

Viale Guglielmo Poletti 30 Alta Valle Intelvi CO
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $77 total per night from Jun 8 to Jun 9
$77 total
Jun 8 - Jun 9
Total with taxes and fees
8.8/10 Excellent! (147 reviews)
"Staff were helpful and rooms were always clean"

Reviewed on Jun 4, 2026

Hotel Funicolare
MOXY Milan Malpensa Airport

MOXY Milan Malpensa Airport

3 out of 5
Milan Malpensa Airport, Terminal 2 Somma Lombardo VA
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $151 total per night from Jun 20 to Jun 21
$151 total
Jun 20 - Jun 21
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
"Good, very well located near T2 and train station"

Reviewed on May 27, 2026

MOXY Milan Malpensa Airport
See all 7,880 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 $1,147 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.