Little Italy holiday rentals

We found 177 holiday rentals — enter your dates for availability

Discover a selection of 17 apartments and other holiday rentals in Little Italy that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the amenities that you expect for your stay, such as Wi-Fi and cable TV. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Little Italy

Showing deals for:15 Aug - 22 Aug

Image gallery for 1600ft² Floor 19 PH w/ Best Views@WestLoop|TheSoul

Living area
9.6 out of 10 rating
Exceptional
(11 reviews)

1600ft² Floor 19 PH w/ Best Views@WestLoop|TheSoul

Chicago, Illinois

8% off
Price is S$8,699
S$1,243 per night
includes taxes & fees
1600ft² Floor 19 PH w/ Best Views@WestLoop|TheSoul

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental accommodation in Little Italy?
The most sought-after types of holiday rentals in Little Italy are apartments. Hoping for something different? Vrbo has a variety of options to match our guests’ unique requirements, so you’ll see properties in loads of sizes and shapes. The perfect home away from home is waiting for you — discover yours today.
How much does it cost to rent a holiday rental in Little Italy?
The average price for a holiday rental in Little Italy is based on a number of factors, including property type, length of stay and season. Whether you’re dreaming about a villa with space for extended family or a cosy cabin just for the two of you, just enter your dates of travel to see stays that offer great value.
How much does it cost to rent a beach house in Little Italy?
Prices for beach houses in Little Italy may differ depending on the type and size of the property and when you plan to travel. All you need to do is enter your travel dates into Vrbo and how many guests to see your options and prices. From there you can use our filter tool to narrow your search by nearby activities, amenities, ratings and more.
Are there pet-friendly holiday rentals in Little Italy?
Pack a travel bag for your pooch because Little Italy has six holiday rentals that welcome pets with open arms. Let your four-legged pal get in on the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your dates and destination, then check the “Pets allowed” filter box.
Can I rent a house with a pool in Little Italy?
Dig out your swimwear and inflatable swan, because there are two houses with a private pool in Little Italy. Book one of these popular holiday homes and you’ll enjoy pool days every day. Simply enter your dates into Vrbo, then check the “pool” filter to find the perfect place to make a splash!
What are popular rental amenities in Little Italy?
A garden, a swimming pool and nearby museums top the list of most popular rental amenities in Little Italy. Whether you’re planning to travel as a party of one, with a partner or as a family group, Vrbo will help you find a holiday rental that suits your style with all the features you’re looking for.
Are there large group holiday rentals in Little Italy?
Take your pick of three Vrbo holiday properties in Little Italy that can accommodate five or more people. You’ll enjoy all the space and privacy you need to spend time with your favourite people — and nobody else.
Are there holiday rentals in Little Italy that welcome kids?
Little Italy has six family-friendly holiday rentals. And securing a stay that welcomes little ones is easy with our “Properties good for families” filter. As well as having the whole place to yourselves, you’ll also enjoy access to perks and amenities like living rooms, kitchens and yards.
What are the top attractions for families in Little Italy?
Keeping the kids happy during your stay in Little Italy is simple with these exciting family-friendly attractions:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom holiday rentals in Little Italy?
You’ll find three one-bedroom properties in Little Italy to pick from. A one-bedroom holiday rental is a great choice if it’s just two of you or if you’re travelling alone. Add in more privacy, convenience and space than a hotel, and you’ve got yourself a getaway to remember.
Are there holiday rentals with WiFi in Little Italy?
Pick from three holiday rentals with WiFi in Little Italy. If you’d like to disconnect from the world on your trip, but still need to be connected to the web, these getaways have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Little Italy?
Decide on your travel dates and then use our filter tool to see holiday rentals with ac in Little Italy on Vrbo. With six air-conditioned properties available, you can look forward to a cool and comfortable break.
How old do you have to be to rent a holiday rental in Little Italy?
We recommend you check with the Little Italy holiday home you’re considering on Vrbo as age restrictions vary. However, typically it’s 16, 18 or 21.
How long can I rent a holiday rental in Little Italy for?
How long you can book a holiday rental in Little Italy depends on the property. Just enter your preferred dates to display a list of options offering extended stays. With tons of amenities such as air conditioning and kitchens, as well as some offering discounted weekly or monthly prices, you’re sure to discover somewhere just right to call your home away from home in Little Italy.

More Holiday Rentals ideas

Oakland Holiday Rentals
Standard Link for Oakland
Catawissa Holiday Rentals
Standard Link for Catawissa
Kapeli Holiday Rentals
Standard Link for Kapeli
San Pablo Lytton Casino Holiday Rentals
Standard Link for San Pablo Lytton Casino
Fox River Preserve Holiday Rentals
Standard Link for Fox River Preserve
Iririki Island Holiday Rentals
Standard Link for Iririki Island
Pine Cove of Sanibel Holiday Rentals
Standard Link for Pine Cove of Sanibel
Forest Glen Holiday Rentals
Standard Link for Forest Glen
Grace Abbott Homes Holiday Rentals
Standard Link for Grace Abbott Homes
Athenaeum Theatre Holiday Rentals
Standard Link for Athenaeum Theatre
Cahokia Holiday Rentals
Standard Link for Cahokia
Oldenburg Holiday Rentals
Standard Link for Oldenburg
Bulverde Holiday Rentals
Standard Link for Bulverde
Chase Tower Holiday Rentals
Standard Link for Chase Tower
Fulton Market Holiday Rentals
Standard Link for Fulton Market
AMITA Health Resurrection Medical Center Chicago Holiday Rentals
Standard Link for AMITA Health Resurrection Medical Center Chicago
Rush and Division Holiday Rentals
Standard Link for Rush and Division
Flossmoor Holiday Rentals
Standard Link for Flossmoor
Briggsville Holiday Rentals
Standard Link for Briggsville
Sauganash Holiday Rentals
Standard Link for Sauganash
Slingerlands Holiday Rentals
Standard Link for Slingerlands
Hyde Park Holiday Rentals
Standard Link for Hyde Park
Washington Park Holiday Rentals
Standard Link for Washington Park
Daan Viljoen Game Reserve Holiday Rentals
Standard Link for Daan Viljoen Game Reserve
Uptown Holiday Rentals
Standard Link for Uptown
Manpho Convention Center Holiday Rentals
Standard Link for Manpho Convention Center
National Corvette Museum Holiday Rentals
Standard Link for National Corvette Museum
Apollo Theater Chicago Holiday Rentals
Standard Link for Apollo Theater Chicago
Logan Square Holiday Rentals
Standard Link for Logan Square
The Galena Territory Holiday Rentals
Standard Link for The Galena Territory