Chiasso Vacations from $706

Book a Hotel + Flight or Car together to unlock savings

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
per person
Oct 30 - Nov 3
found 16 hours ago
Roundtrip non-stop flight included
New York (NYC) to Milan (LIN)
8.8/10 Excellent! (1,004 reviews)
Beautiful hotel with an excellent staff. Getting still water was an issue. The pool area didnt have enough chairs. The scrambled eggs for breakfast was like "egg soup" not cooked enough. Location was a distance from any relevant sites. 20 euro taxi ride.

Reviewed on Aug 13, 2025

Nuvole Garden Hotel

Nuvole Garden Hotel

5 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Milan (MXP)
7.2/10 Good! (5 reviews)
Wonderful property with spectacular views.

Reviewed on Jul 4, 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
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip flight included
New York (JFK) to Milan (LIN)
9.8/10 Exceptional! (79 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
Save 100% on your flight
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Milan (LIN)
8.6/10 Excellent! (1,010 reviews)
Great location! Very good hotel with excellent quality and service. Congratulations to all the staff.

Reviewed on Aug 16, 2025

Hotel Crivi's

Hotel Crivi's

4 out of 5
Milan Centre
Save 100% on your flight
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Milan (LIN)
8/10 Very Good! (323 reviews)
Nice place. Quiet and good location.

Reviewed on Aug 13, 2025

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

Chiasso Hotel Deals

Hotel Cruise

Hotel Cruise

4 out of 5
Via Carducci, 3, Montano Lucino, CO
$121 nightly
The price is $133 total per night from Aug 20 to Aug 21
$133 total
Aug 20 - Aug 21
Total includes taxes and fees
8.6/10 Excellent! (1,002 reviews)
"There was no kettle. Would suggest hotel keeps hot water kettle for tea and coffee"

Reviewed on Aug 10, 2025

Hotel Cruise
Grand Hotel Villa Serbelloni

Grand Hotel Villa Serbelloni

5 out of 5
Via Teresio Olivelli 1, Bellagio, CO
9.2/10 Wonderful! (522 reviews)
"The property was beautiful, especially the outside and the pool area. The interior left me wanting more."

Reviewed on Aug 15, 2025

Get rates
Grand Hotel Villa Serbelloni
Palace Hotel

Palace Hotel

4 out of 5
Lungo Lario Trieste, 16, Como, CO
Fully refundableReserve now, pay when you stay
$364 nightly
The price is $412 total per night from Aug 20 to Aug 21
$412 total
Aug 20 - Aug 21
Total includes taxes and fees
9.2/10 Wonderful! (1,003 reviews)
"Exceptionally located, convenient, incredible service and attention to guests ( Alessia was beyond expecations and gave us attention), food and staff always ready and pleasant, everything was close by, just a delight to stay at this hotel. Highly recommended."

Reviewed on Aug 11, 2025

Palace Hotel
See all 7,642 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.

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 $706 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.