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 $2,795, price is now CA $1,966 per person
CA $1,966
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Milan (MXP)
8.2/10 Very good! (394 reviews)
En realidad en todo Milano la gente no es muy amable, entonces no podía esperar algo diferente

Reviewed on Jul 8, 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 $4,815, price is now CA $2,900 per person
CA $2,900
per person
Sep 21 - Sep 27
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milan (MXP)
9.4/10 Exceptional! (574 reviews)
Unbelievably friendly staff, really quirky rooms that are really well designed and furnished. A very stylistic and unique Hotel

Reviewed on Jul 9, 2026

Uptown Palace

Uptown Palace

4 out of 5
Milan Centre
Price was CA $4,037, price is now CA $2,514 per person
CA $2,514
per person
Sep 21 - Sep 27
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milan (MXP)
8.6/10 Excellent! (1,005 reviews)
The breakfast was pretty good and was included in our room rate, but the scrambled eggs were powdered eggs (they were terrible) and if you want fresh cracked eggs you paid 8-12 euros. We stayed in the presidential suite. It was very nice and large room and had a nice view of the Duomo. The outdoor balcony was very large too. Unfortunately, the lobby chairs and sofas need to be updated. They smelled bad and had stains on them. Otherwise, you are about a 10 minute walk from the galleria shopping area. Nice hotel and once they update the lobby furniture, it will be much better.

Reviewed on Jun 30, 2026

Grand Visconti Palace

Grand Visconti Palace

4 out of 5
Porta Lodovica
Price was CA $3,575, price is now CA $2,447 per person
CA $2,447
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Milan (MXP)
8.8/10 Excellent! (1,000 reviews)
Rooms were nice except old small tv, there were no bathrobes, pool was additional 20€ per person…. Parking 35€ and 10 € tax per person. Staff was nice!

Reviewed on Jul 10, 2026

Palazzo Cordusio Gran Meliá – The Leading Hotels of the World

Palazzo Cordusio Gran Meliá – The Leading Hotels of the World

5 out of 5
Milan Centre
Price was CA $5,562, price is now CA $4,096 per person
CA $4,096
per person
Aug 21 - Aug 26
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Milan (MXP)
9.6/10 Exceptional! (59 reviews)
Very centrally located.

Reviewed on Jul 7, 2026

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Chiasso Hotel Deals

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 $452 per night from Aug 6 to Aug 7
CA $452
CA $514 total
Aug 6 - Aug 7
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"We were given a free upgrade to a suite which had 2 balconies, perfect for viewing the lake! Reception was very helpful in giving us information about the activities in Como, and the breakfast was great!"

Reviewed on Jul 10, 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 $136 per night from Jul 20 to Jul 21
CA $136
CA $150 total
Jul 20 - Jul 21
includes taxes & fees
9/10 Wonderful! (190 reviews)
"It was all good"

Reviewed on Jul 2, 2026

Hotel Funicolare
Novotel Milan Malpensa Airport

Novotel Milan Malpensa Airport

4 out of 5
Via Al Campo 99 Cardano al Campo VA
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Aug 1 to Aug 2
CA $159
CA $175 total
Aug 1 - Aug 2
includes taxes & fees
8/10 Very good! (1,014 reviews)
"The carpet floor didn’t look clean although the bed was really clean and tidy. Bathroom was decent but needed extra towels for a family of four. The lobby was warm, didn’t know if it was the crowd of people checking in or a problem with the A/C. Other family members were also staying here and their ..."

Reviewed on Jul 11, 2026

Novotel Milan Malpensa Airport
See all 7,917 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

Cinema Theatre Chiasso

Enjoy a show at Cinema Theatre Chiasso, a storied theater in Chiasso. Wander the lakeside or discover the area's mountain views.
See properties

Frequently asked questions

How much does a Chiasso vacation package cost?
Offering great value package deals from CA $1,966 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.

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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.