Little Italy holiday lettings

We found 167 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.

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Why visit Little Italy

  • Authentic Italian Cuisine: Savor delicious traditional dishes at local restaurants, showcasing the rich culinary heritage of Italy.
  • Cultural Experience: Immerse yourself in the vibrant Italian-American culture through festivals, art, and historic landmarks.
  • Charming Neighbourhoods: Explore picturesque streets filled with unique shops, cafes, and friendly locals.
  • Family-Friendly Activities: Enjoy parks and recreational areas that cater to all ages, perfect for family outings.
  • Diverse Nearby Areas: Discover the vibrant communities of Little Village and others, enhancing your adventure.

Popular types of accommodation around Little Italy

You've chosen to explore Little Italy, and now the excitement begins with selecting your accommodation. From charming apartments to spacious private homes and stylish condos, Little Italy offers a variety of options to suit your needs. Whether you’re searching for Little Italy apartments, Italy apartments, or Chicago IL apartments, you'll find the perfect base for your adventures. Discover the best places to stay and enjoy all that this vibrant area has to offer.

  • Apartments: The most sought-after option in Little Italy, providing a comfortable and convenient stay for visitors.
  • Houses: A popular choice for those seeking a homely atmosphere, ideal for families or groups.
  • Condos: A trendy and modern accommodation type, perfect for those wanting a stylish base in the heart of the area.
  • Cottages: Charming and quaint, these rentals offer a unique experience away from the bustle.
  • Villas: Luxurious options that provide ample space and amenities for a lavish getaway.**

Top attractions near Little Italy

Little Italy in Chicago is an ideal destination for families and those seeking a vibrant city experience. Visitors can explore an array of attractions, including urban parks, iconic skyscrapers, and historic buildings. This charming area offers a rich cultural experience, perfect for travellers looking to immerse themselves in the local heritage while enjoying outdoor activities.

  • McCormick Place: A premier event and conference venue with a professional atmosphere, McCormick Place hosts a variety of conventions and exhibitions. Experience the vibrant energy of business and innovation while enjoying its impressive architecture and facilities.
  • Michigan Avenue: Known as the Magnificent Mile, this bustling street is lined with high-end shops, restaurants, and iconic landmarks. Immerse yourself in the city's lively urban energy, perfect for shopping and people-watching.
  • Grant Park: A sprawling urban park offering a family-friendly atmosphere, Grant Park features beautiful gardens, walking paths, and open spaces. Enjoy outdoor activities and cultural events while soaking in stunning city views.

Things to do recommended for couples

For a romantic getaway in Little Italy, enjoy live music at the House of Blues or indulge in a lovely meal at the Historic Michael Jordan Restaurant, both a mere 1.2km away. For an unforgettable evening, consider a concert at the Aragon Ballroom, located 4.3km away.

Things to do recommended for families

Families will delight in the lively atmosphere at Wrigley Field, only 3.7km from Little Italy, and can unwind at the tranquil Northerly Island Natural Area, 1.9km away. The East Bank Club, located 1.2km from Little Italy, offers further opportunities for relaxation and wellness.

Things to do recommended for groups

Experience the vibrant culture of Little Italy by catching a show at the Chicago Theatre, just 1.2km away. For a good laugh, head to Second City, 1.9km away, perfect for family fun. Don't forget to explore Chicago Place Mall, also 1.9km away, for some shopping.

What do I need to keep in mind when booking a vacation around Little Italy

When you're planning a trip, whether it's with a group, your family, or pets, or if you're seeking extended stays, be sure to use the appropriate filters to match your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Little Italy with a group: Think about how many bedrooms you require, along with any amenities like a fully-equipped kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Little Italy with young kids: Journeying with young children can present its difficulties. It's essential to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Little Italy: For many, a family holiday isn’t quite the same without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Little Italy: If you’re in search of holiday rentals that offer discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include preferences such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Little Italy

Little Italy in Chicago offers a charming blend of urban vibrancy and family-friendly atmosphere, making it an ideal destination for those seeking cultural experiences. Nearby, explore the diverse neighbourhoods of Little Village and other affordable areas that showcase friendly locals and beautiful scenery. Whether you’re indulging in authentic Italian cuisine or enjoying the lively streets, Little Italy promises a delightful and memorable vacation experience.

  • Chicago: Chicago is a vibrant metropolis located a mere 1.2km from Little Italy. This city offers a delightful blend of family-friendly activities, outdoor adventures, and urban experiences. Visitors can indulge in shopping at renowned retail areas, catch thrilling sports events at local stadiums, and explore educational attractions. With its lively tourist precincts and an array of entertainment options, including arenas and cultural venues, Chicago is a must-visit for anyone seeking a dynamic city experience.
  • Downtown Chicago: Just 1.2km from Little Italy, Downtown Chicago is the bustling heart of the city. This neighbourhood is perfect for families and outdoor enthusiasts alike, featuring a plethora of shopping areas and theatre venues for cultural immersion. Visitors can enjoy the stunning architecture, vibrant streets, and engaging attractions like sports facilities and major tourist precincts. The blend of entertainment and urban charm makes Downtown Chicago an essential stop on your journey.
  • The Loop: The Loop, located 1.2km from Little Italy, is another iconic neighbourhood worth exploring. Known for its family-oriented atmosphere and outdoor spaces, it offers a unique city-themed experience. The Loop is home to excellent shopping districts, impressive theatre performances, and urban parks for relaxation. With its proximity to notable landmarks like stadiums and tourist precincts, The Loop captures the essence of Chicago’s dynamic spirit, making it a delightful addition to your travel itinerary.

Best time to go to Little Italy

If you're planning a trip to Little Italy, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudyModerately LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyModerately LowSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnyModerately HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnyModerately HighSlightly High
August73.0°F (22.8°C)Light RainMostly SunnyModerately HighSlightly High
September67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
October54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is simple

Looking to make the most of your next holiday while keeping costs down? Consider being flexible with your travel dates, as this can lead to significant price differences. Moreover, opting for a longer stay frequently results in excellent savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to narrow your search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides you with a convenient platform to plan new adventures, manage your existing arrangements, or organise your bookings. Your saved or reserved properties are neatly categorised into Potential, Upcoming, or Current Trips. To discover Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in Little Italy?
In Little Italy, apartments are the most popular type of holiday rental, with about 12 available in the area. These apartments are typically situated in charming neighbourhoods, providing guests with a homely atmosphere. Most units come equipped with essential amenities, including fully stocked kitchens, comfortable living spaces, and sometimes even balconies to enjoy the local views. This makes them a convenient choice for both short and extended stays, allowing visitors to immerse themselves in the vibrant culture and dining options of Little Italy.
How much does it cost to rent a holiday home in Little Italy?
Prices for holiday rentals in Little Italy vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Little Italy to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Little Italy holiday house rentals?
You can find great discounts on house rentals in Little Italy on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Little Italy?
In Little Italy, popular holiday rental amenities cater to families and travellers seeking comfort and convenience. Most accommodations feature fully equipped kitchens, allowing guests to prepare their meals easily. Many rentals also provide air conditioning to ensure a comfortable atmosphere, especially during warmer months. For families with young children, amenities such as travel cribs and books for children are commonly available, making it easier for parents to travel without needing to bring extra supplies. Additionally, you'll often find coffee and tea makers, great for enjoying a warm beverage in the morning or after a day of exploring the local neighbourhoods and nearby attractions.
Can I find family house rentals in Little Italy?
In Little Italy, Illinois, there are several family-friendly house rentals available, making it a delightful choice for families seeking a stay in this vibrant neighbourhood. The area is renowned for its rich Italian heritage and close-knit community atmosphere, providing a warm welcome to visitors.

Many of these homes offer ample living space, allowing families to relax together after a day of exploring. You can expect features such as fully equipped kitchens, where you can prepare meals, and comfortable dining areas superb for family gatherings. Some properties may even have outdoor spaces, ideal for enjoying the pleasant weather.

Additionally, Little Italy is conveniently located near several family-friendly attractions. The nearby University of Illinois at Chicago offers lovely parks, and the Chicago Children's Museum is just a short drive away, providing plenty of opportunities for fun and learning.
Are there any Little Italy holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Little Italy with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I book pet-friendly holiday rentals in Little Italy?
In Little Italy, there are several pet-friendly holiday rentals available, providing a welcoming environment for travellers with pets. Many of these accommodations come equipped with essential amenities such as well-appointed kitchens, comfortable living spaces, and access to outdoor areas where pets can enjoy the fresh air.

The neighbourhood itself is rich in cultural heritage, with lovely parks nearby, such as the expansive Douglas Park, which offers walking paths and open spaces for pets to roam. Additionally, the area features a variety of pet-friendly cafes and shops, ensuring that you and your furry companion have plenty of options for outings and relaxation.
Can I find long-stay holiday rentals in Little Italy?
A long-stay holiday rental in Little Italy is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Little Italy for a holiday rental?
The peak time to visit Little Italy is between May and July, when the neighbourhood bursts to life with vibrant festivals, outdoor dining, and a variety of cultural events. July stands out as the most popular month, drawing both locals and tourists who flock to enjoy the warm weather and lively option, great for indulging in the delicious cuisine that Little Italy is known for.

During these summer months, visitors can relish mild to warm temperatures, typically ranging from 20 to 30 degrees Celsius, making it ideal for exploring the charming streets and historic sites. Outdoor activities, such as strolling through the picturesque parks or dining al fresco at one of the many Italian restaurants, become even more enjoyable with the pleasant climate.

For those looking for a more budget-friendly experience, consider planning your visit in December. While this month may be quieter, it offers a unique charm with festive decorations and a chance to enjoy the local culture at a more relaxed pace. Plus, visitors can still savour the delightful seasonal dishes that bring a taste of Italy to the winter months.

Ultimately, the best time to book your holiday rental in Little Italy greatly depends on your preferences.
Are there any remote work holiday rentals in Little Italy?
In Little Italy, Illinois, there are several remote work-friendly holiday rentals available, with around 12 options to choose from. These properties cater well to those needing to balance work and leisure, often featuring dedicated office spaces and high-speed internet connections. Many accommodations come equipped with complimentary Wi-Fi, ensuring seamless connectivity for remote working.

The neighbourhood itself is rich in culture, with a variety of local eateries and vibrant community life, making it a delightful place to stay while working remotely. Additionally, travellers can expect amenities such as comfortable work desks, spacious living areas for relaxation, and convenient access to nearby parks or cafes for a change of scenery during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Little Italy holiday rental?
Book your Little Italy holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Little Italy, Illinois, United States of America?
In Little Italy, Illinois, visitors can experience firsthand a rich cultural experience characterised by its Italian heritage. The area is renowned for its vibrant dining scene, featuring authentic Italian restaurants and cafes that draw locals and tourists alike. A must-visit is the University Village, which is nearby and offers a mix of educational institutions and charming shops.

One of the highlights of Little Italy is the National Italian American Sports Hall of Fame, celebrating the achievements of Italian Americans in sports. Additionally, the neighbourhood is close to Taylor Street, often referred to as the heart of Little Italy, where you can find lively festivals, markets, and local events that showcase the community's spirit.

For those interested in history, the area is also within reach of the historic Chicago Stockyards, where you can learn about the city's past in relation to the meatpacking industry. The proximity to the University of Illinois at Chicago also provides opportunities to engage in cultural events and activities hosted by the campus.
Can I change or cancel my Little Italy home rental booking on Vrbo?
To find Little Italy holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Little Italy holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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