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.
Hotel Crivi's

Hotel Crivi's

4 out of 5
Milan Centre
Price was CA $2,399, price is now CA $1,677 per person
CA $1,677
per person
Oct 10 - Oct 16
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milan (MXP)
8.2/10 Very good! (400 reviews)
Breakfast was lovely and staff welcoming. Plenty of trams and buses available. We walked from Milano Central to the hotel - 1 hour. Pleasant walk on the flat. Walk to the city centre approximately 15 minutes. The hotel was spotless and well maintained, decor a little dated (90s). Would recommend and would stay again.

Reviewed on Jul 24, 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 CA $5,423, price is now CA $2,925 per person
CA $2,925
per person
Sep 20 - Sep 26
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Milan (MXP)
9.4/10 Exceptional! (591 reviews)

Kleos Hotel Milano by Kleos Group Collection

Kleos Hotel Milano by Kleos Group Collection

3 out of 5
Città Studi
Price was CA $3,735, price is now CA $2,533 per person
CA $2,533
per person
Sep 20 - Sep 26
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Milan (MXP)
8.4/10 Very good! (84 reviews)
The room is clean despite of not very spacious. The location is not very close to the main attraction but close to underground station from where take about 2-3 stops to the town centre.

Reviewed on Jul 7, 2026

Art Hotel Navigli

Art Hotel Navigli

4 out of 5
Navigli
Price was CA $2,721, price is now CA $1,858 per person
CA $1,858
per person
Oct 10 - Oct 16
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milan (MXP)
9/10 Wonderful! (1,002 reviews)
From check in, to arranging transportation for traveling home- this was a fantastic experience. Generous breakfast available everyday, afternoon cookies and a crazy complimentary antipasti evening spread were welcomed surprises. Walkable to any place in Navigli, a great center of nightlife. Cool and modern- loved it!

Reviewed on Jul 30, 2026

DBH Duomo Boutique Hotel Lake Como

DBH Duomo Boutique Hotel Lake Como

4 out of 5
Como City Centre
Price was CA $6,056, price is now CA $4,364 per person
CA $4,364
per person
Sep 20 - Sep 26
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Milan (MXP)
9.8/10 Exceptional! (208 reviews)
DBH is probably one of the most hospitable boutique hotels I’ve ever stayed in, the front desk staff is exceptional and truly seems to care. We had a no-so-fun issue as first timers in the area and did not know about the zoning restrictions as it was a last minute booking. Usually a hotel will send a message to let you know where to drive/park, but we literally booked DBH 30 minutes before we arrived. So silly us just drove up to the front of the hotel! Note to all guests with cars, this is a no no in the area as the location is literally next to the stunning Duomo. I did not have time to do my usual research. All that said, the staff went above and beyond to get us taken care of and get our room prepared quickly for my family of 3. The room had everything we needed. Breakfast on the front patio was lovely as well and had air conditioning. The location was perfect as well, all sorts of restaurants and shops around. Quick stay but we will definitely save it for our next visit to Como!

Reviewed on Jul 31, 2026

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Chiasso Hotel Deals

Villa Sassa

Villa Sassa

4 out of 5
Via Tesserete 10 Lugano TI
Fully refundableReserve now, pay when you stay
The price is CA $325 per night from Aug 30 to Aug 31
CA $325
CA $354 total
Aug 30 - Aug 31
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"While the views of Lake Lugano are on point, the place is outdated and in dire need of renovation. We stayed in a Grand Suite, but cooling was a major issue, there were only two AC units for four bedrooms and a living room, which is unacceptable. We ended up dragging a mattress into the living room ..."

Reviewed on Aug 2, 2026

Villa Sassa
Hotel Barchetta Excelsior

Hotel Barchetta Excelsior

4 out of 5
Piazza Cavour 1 Como CO
Fully refundableReserve now, pay when you stay
The price is CA $458 per night from Aug 31 to Sep 1
CA $458
CA $520 total
Aug 31 - Sep 1
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Great location overlooking the water. Walkable and great city. Super easy to take ferries to other cities like Bellagio. The ferry is literally across the street. This was our favorite spot (hotel and location) of the Italy tour."

Reviewed on Aug 2, 2026

Hotel Barchetta Excelsior
Hotel Funicolare

Hotel Funicolare

Viale Guglielmo Poletti 30 Alta Valle Intelvi CO
Fully refundableReserve now, pay when you stay
The price is CA $101 per night from Aug 31 to Sep 1
CA $101
CA $111 total
Aug 31 - Sep 1
includes taxes & fees
Hotel Funicolare
See all 8,104 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.
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Stay near popular Chiasso attractions

Via Gottardo

You can take time to visit Via Gottardo during your travels to Chiasso. Take in the theater scene while you're in the area.
See properties

Frequently asked questions

How much does a Chiasso vacation package cost?
Offering great value package deals from CA $1,677 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.