Chiasso Vacation Packages

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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.

Top Chiasso Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Enterprise Hotel

Enterprise Hotel

4 out of 5
Porta Sempione
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Milan (LIN)
8.8/10 Excellent! (1,003 reviews)
Hotel ben strutturato, silenzioso, e posizionato in punto strategico, molto vicino a San siro e alla zona degli affari, colazione molto variegata.

Reviewed on Jul. 29, 2025

Uptown Palace

Uptown Palace

4 out of 5
Milan Centre
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Milan (LIN)
8.6/10 Excellent! (1,000 reviews)
We were very happy with the pleasant surprise brought by the reception, which was very welcoming, respectful, generous, and surprising. Not only was our check-in earlier, but we also received an upgrade to a huge, chic, modern apartment with a stunning view of Milan. Wow! For someone who traveled so many hours from Brazil, this gesture was truly a warm welcome! Thank you all so much yesterday morning. You made a difference in our lives! We'll be back!

Reviewed on Aug. 5, 2025

Grand Visconti Palace

Grand Visconti Palace

4 out of 5
Porta Lodovica
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Milan (LIN)
8.8/10 Excellent! (1,006 reviews)
Near Bocconi University

Reviewed on Jul. 29, 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
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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

Nuvole Garden Hotel

Nuvole Garden Hotel

5 out of 5
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Milan (MXP)
7.2/10 Good! (5 reviews)
Wonderful property with spectacular views.

Reviewed on Jul. 4, 2025

Ready to book your vacation to Chiasso?

 

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Chiasso Hotel Deals

Palace Hotel

Palace Hotel

4 out of 5
Lungo Lario Trieste, 16, Como, CO
Fully refundableReserve now, pay when you stay
The price is CA $465 per night from Aug 21 to Aug 22
CA $465
CA $528 total
Aug 21 - Aug 22
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Nice hotel and very central location, friendly staff"

Reviewed on Aug. 4, 2025

Palace Hotel
Hotel Cruise

Hotel Cruise

4 out of 5
Via Carducci, 3, Montano Lucino, CO
The price is CA $174 per night from Aug 10 to Aug 11
CA $174
CA $191 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"Location is near Como but you need a car. Breakfast was very good. Rooms were nice and clean, and a/c worked well."

Reviewed on Aug. 1, 2025

Hotel Cruise
Holiday Inn Express Milan - Malpensa Airport by IHG

Holiday Inn Express Milan - Malpensa Airport by IHG

3 out of 5
Via de Pinedo Ang., Via Oldrini Case Nuove, Somma Lombardo, VA
Fully refundable
The price is CA $129 per night from Aug 27 to Aug 28
CA $129
CA $144 total
Aug 27 - Aug 28
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"Nice location. Comfortable.,"

Reviewed on Jul. 26, 2025

Holiday Inn Express Milan - Malpensa Airport by IHG
See all 7,623 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Chiasso vacation package cost?
Offering great value package deals from CA $1,540 on Expedia, you'll be surprised at how little a vacation to Chiasso costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Chiasso?
To pick up cheap Chiasso vacation packages, organize your getaway outside of peak periods like public holidays and major events. You'll generally find lower prices and better availability for flights and hotels.
How many days is enough for Chiasso?
Allow at least 2 days for your Chiasso vacation to really enjoy everything that makes this place unique. Stroll around key areas, including Caneggio and San Pietro. Then check out major sights like Generoso Mount and Baumgartner Model Railway Gallery. With a well-planned itinerary, you'll be kept busy with room for some rest and relaxation too. Want to venture outside of Chiasso? Consider squeezing in a day trip or two.
Is it worth booking a vacation package to Chiasso?
Whether you're planning to visit attractions like Via Gottardo and Cinema Theatre Chiasso, or want to experience its top-notch walking trails and culture, a Chiasso vacation guarantees an unforgettable adventure. Book your trip with Expedia and find out why Chiasso is such a good vacation destination.
How to find the best Chiasso package deals?
Use Expedia's filter tool to help you find some tempting Chiasso package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Chiasso package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Chiasso vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations separately. Better still, you can customize your Chiasso getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Chiasso?
If you're considering a spontaneous Chiasso adventure, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Chiasso?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to go to Chiasso.
  2. Set your budget: Factor in expenses like food, flights and transportation when working out how much to save for your trip to Chiasso. Then, select a property that works with your budget, whether that's an economical option or a swankier retreat.
  3. Work out your trip length: Think about how much time you want to spend exploring Chiasso. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your accommodations and airfare: After you've settled on your trip dates and duration, lock in the right Chiasso vacation package for you.

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