Chiasso Vacations from $1,060

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to $1,045 when you book a flight and hotel together*

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Hotel Brunelleschi

Hotel Brunelleschi

4 out of 5
Milan Centre
Price was $1,412, price is now $1,060 per person
$1,060
per person
Jan 3 - Jan 8
found 1 hour ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Milan (LIN)
8.8/10 Excellent! (1,212 reviews)
Clean room, helpful staff.

Reviewed on Oct 13, 2025

Casa Baglioni Milan - The Leading Hotels of the World

Casa Baglioni Milan - The Leading Hotels of the World

5 out of 5
Milan Centre
Save 100% on your flight
Price was $6,458, price is now $4,143 per person
$4,143
per person
Dec 29 - Jan 3
found 12 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Milan (LIN)
9.8/10 Exceptional! (83 reviews)
Perfect boutique hotel in a chic neighborhood. Would definitely come back

Reviewed on Jul 31, 2025

Uptown Palace

Uptown Palace

4 out of 5
Milan Centre
Price was $1,551, price is now $1,082 per person
$1,082
per person
Jan 3 - Jan 8
found 1 hour ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Milan (LIN)
8.6/10 Excellent! (1,010 reviews)
Good location walking distance to Piazza Duomo. Hotel is nice and clean except you can hear the rush of flowing water from the wall. Good breakfast in their restaurant located on the top floor with excellent views. Staff was helpful except during check in when I mentioned that I have Expedia VIP status, they kind of just laughed and said “Ok, so?” I told them I’m supposed to mention it when I check in. Anyway, I asked again later on in the day and I was told to just pick a bottle of wine or prosecco from the mini fridge. There were no wines in the fridge. There was a small bottle of Prosecco so I just didn’t bother at all.

Reviewed on Oct 13, 2025

Hotel Ansitz Plantiz

Hotel Ansitz Plantiz

5 out of 5
Save 100% on your flight
Price was $1,574, price is now $1,135 per person
$1,135
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Milan (MXP)
9.6/10 Exceptional! (83 reviews)
Nice place and nice staff. Had to pay for sending a jacket they had, without my knowledge, offloaded from the inside of the car, not trunk, and hanged it in a closet. Would have been nice for them to pay the transport but OK.

Reviewed on Apr 20, 2025

Nuvole Garden Hotel

Nuvole Garden Hotel

5 out of 5
Save 100% on your flight
Price was $4,961, price is now $3,703 per person
$3,703
per person
Dec 29 - Jan 3
found 12 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Milan (MXP)
7.8/10 Good! (6 reviews)
Wonderful property with spectacular views.

Reviewed on Jul 4, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chiasso
View all trips

Chiasso Hotel Deals

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
$117 nightly
The price is $130 total per night from Nov 2 to Nov 3
$130 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,016 reviews)
"A great place to overnight for morning air travel from Milan Malpensa airport. No problems…highly recommend!"

Reviewed on Oct 13, 2025

MOXY Milan Malpensa Airport
Hotel Cruise

Hotel Cruise

4 out of 5
Via Carducci, 3, Montano Lucino, CO
$83 nightly
The price is $92 total per night from Nov 2 to Nov 3
$92 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (1,009 reviews)
"Clean room, great location"

Reviewed on Oct 1, 2025

Hotel Cruise
Grand Hotel Villa Serbelloni

Grand Hotel Villa Serbelloni

5 out of 5
Via Teresio Olivelli 1, Bellagio, CO
Fully refundableReserve now, pay when you stay
$792 nightly
The price is $883 total per night from Oct 14 to Oct 15
$883 total
Oct 14 - Oct 15
Total with taxes and fees
9.2/10 Wonderful! (540 reviews)
"We traveled to Bellagio early October 2025 for our honeymooon!! This hotel was amazing - it is absolutely the best place to stay in all of Lake Como, and possibly all of Italy. The staff were extremely friendly, helpful, and attentive. They often remembered our drink orders from the previous day ..."

Reviewed on Oct 7, 2025

Grand Hotel Villa Serbelloni
See all 7,757 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.

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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chiasso vacation package cost?
Offering great value package deals from $1,060 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.

Explore a world of travel with Expedia

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