Heart of Chicago holiday rentals
We found 50 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Heart of Chicago that are perfect for your trip. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as cable TV and a washer and dryer. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.
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Find the best place to stay - Heart of Chicago

Spacious Modern Pilsen Retreat | Sleeps 8 | Near Downtown Chicago
Sleeps 8 · 3 bedrooms · 2 bathrooms

Cozy Charming •Art 🎨 • Food🌮 Close to Train 🚉 • Parking!
Sleeps 4 · 2 bedrooms · 1 bathroom

Pilsen Retreat: 4BR 3BA near Downtown Chicago
Sleeps 8 · 4 bedrooms · 3+ bathrooms

Charming retreat w/fireplace
Sleeps 8 · 1 bedroom · 1+ bathroom

Luxury Modern home minutes from Downtown Chicago
Sleeps 5 · 3 bedrooms · 2 bathrooms

Spacious Pilsen 3BR Apt,AC,Laudry,Free Parking
Sleeps 6 · 3 bedrooms · 1 bathroom
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental in Heart Of Chicago?
In the Heart of Chicago, apartments are the most popular type of holiday rental, with approximately 104 options available in the bustling city centre. These apartments are often situated near major attractions such as Millennium Park, the Art Institute of Chicago, and the vibrant shopping district along State Street. Guests can expect amenities like fully equipped kitchens, modern furnishings, and access to fitness facilities or rooftop terraces that offer stunning views of the skyline.Additionally, there are around 12 condos and 12 holiday houses available for those seeking a different atmosphere. Condos typically offer similar amenities to apartments but may include additional features like private balconies or access to communal pools and lounges. Holiday houses provide more space, making them ideal for families or groups, often featuring larger living areas, outdoor spaces, and multiple bedrooms.
Are there any beach house rentals in Heart Of Chicago?
In the Heart of Chicago, there are several beach house rentals available, primarily situated near Lake Michigan. These rentals offer unique amenities that cater to travellers looking for a home-like experience while enjoying the vibrant city. Most beach houses typically feature spacious living areas, fully equipped kitchens, and outdoor spaces such as balconies or patios where guests can relax and take in views of the lake.The area provides easy access to popular attractions, including Millennium Park and the Art Institute of Chicago, making these rentals a convenient base for exploring the city.
What are popular rental amenities in Heart Of Chicago?
In the Heart of Chicago, popular holiday rental amenities include fully equipped kitchens, which allow guests to prepare their own meals and enjoy the local cuisine at their leisure. Many rentals also feature coffee and tea makers, providing a convenient way to enjoy a warm beverage at any time. Onsite parking is another sought-after amenity, making it easier for visitors with vehicles to explore the city without the hassle of street parking. Additionally, many properties come with decks or patios, offering outdoor spaces where guests can relax and take in the vibrant city atmosphere.
Can I find family house rentals in Heart Of Chicago?
In the Heart of Chicago, there are numerous family-friendly house rentals available, with around 15 properties to choose from. This vibrant area features a mix of neighbourhoods, such as Lincoln Park and Lakeview, both of which are ideal for families seeking a city adventure. Many of these homes offer spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play or families can gather.Visitors will find themselves close to several attractions, including the Lincoln Park Zoo and the Museum of Science and Industry, both superb for family outings. Amenities like Wi-Fi, air conditioning, and laundry facilities are commonly featured, ensuring a comfortable stay for all ages.
Can I rent a holiday home with a pool or hot tub in Heart Of Chicago?
In the Heart of Chicago, there are several holiday homes available for rent that feature hot tubs, offering a great way to unwind after a day of exploring the city. This vibrant area includes popular neighbourhoods such as the Loop, River North, and the Near North Side, each providing a mix of modern amenities and local charm.Travellers can expect properties with various amenities, including private hot tubs, spacious living areas, and fully equipped kitchens. Many rentals are designed for comfort, featuring Wi-Fi and air conditioning to ensure a pleasant stay. Some homes may also offer access to shared pools or rooftop terraces, providing fantastic views of the iconic Chicago skyline.
Can I book pet-friendly holiday rentals in Heart Of Chicago?
In the Heart of Chicago, travellers can indeed find several pet-friendly holiday rentals. This vibrant area offers a range of accommodations that typically feature modern amenities such as fully equipped kitchens, spacious living areas, and Wi-Fi. Many properties are designed with comfort in mind, making them suitable for both pets and their owners.The neighbourhood is conveniently located near several parks, providing ample opportunities for walks and outdoor activities with pets. Grant Park, a significant green space in the city, is just a short distance away, featuring walking trails and open lawns great for enjoying some fresh air. Additionally, the proximity to pet-friendly cafes and restaurants enhances the experience for visitors travelling with their furry companions.
When is the best time to visit Heart Of Chicago for a holiday rental?
The peak season for visiting the Heart of Chicago runs from May to July, making it an ideal time for those seeking vibrant city life and outdoor fun. With the summer heat and long days, July stands out as the most popular month, attracting visitors eager to explore the city's rich culture, iconic architecture, and bustling festivals.During this period, temperatures typically hover around 20 to 30 degrees Celsius, providing a comfortable climate for outdoor activities. You can enjoy leisurely strolls along the scenic Lakefront Trail, visit Millennium Park for free concerts, or indulge in the city's renowned dining scene. The lively option is complemented by numerous street festivals and events, superb for those looking to immerse themselves in the local vibe.For travellers who are mindful of their budget, November presents a wonderful opportunity to enjoy the city at a quieter pace. While the summer crowds have dissipated, you can still explore the fascinating museums, such as the Art Institute of Chicago, and experience the city's architecture without the usual hustle and bustle. Plus, the fall foliage adds a beautiful touch to the city's parks.Ultimately, the best time to visit the Heart of Chicago for a holiday rental depends on whether you're looking for the excitement of peak season in summer or the charm of a quieter, more reflective experience in the fall.
Are there any remote work holiday rentals in Heart Of Chicago?
In the Heart of Chicago, there is a wealth of remote work holiday rentals available, with around 108 options to choose from. This bustling urban area offers a vibrant setting, ideal for both work and leisure. Many of these rentals are equipped with essential amenities for remote work, including high-speed internet access, dedicated desk spaces, and ergonomic desk chairs, ensuring a comfortable work environment.Properties are often situated near key attractions, such as Millennium Park, the Art Institute of Chicago, and the iconic Magnificent Mile, providing easy access to cultural experiences and dining options during breaks. The rentals typically feature modern conveniences, including Wi-Fi, comfortable living spaces, and sometimes even in-unit laundry facilities, catering perfectly to the needs of business travellers or those seeking a blend of work and leisure in the city. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are the top attractions in Heart Of Chicago, Illinois, United States of America?
In the Heart of Chicago, visitors can take part in a range of attractions that showcase the city's vibrant culture and history. Millennium Park is a must-visit, featuring the iconic Cloud Gate sculpture, commonly known as "The Bean," and beautifully landscaped gardens. Nearby, the Art Institute of Chicago boasts an impressive collection of artworks from around the world and is easily accessible from various holiday rentals in the area.Another popular area is the Magnificent Mile, where visitors can indulge in shopping at high-end boutiques and enjoy dining at renowned restaurants. The historic Chicago Water Tower, located on this famous stretch, serves as a picturesque landmark.For those interested in theatre and live performances, the Chicago Loop offers a number of options, including the renowned Chicago Shakespeare Theater and the Cadillac Palace Theatre.Additionally, the nearby Navy Pier is superb for family outings, offering amusement rides, dining options, and stunning views of Lake Michigan.
Are all fees included in the Heart of Chicago holiday homes prices shown on Stayz?
Stayz 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.
Are there any Heart of Chicago holiday homes with parking?
Stayz offers a wide selection of holiday homes in Heart of Chicago 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 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.
Are there any discounts for Heart of Chicago holiday homes?
You can find great discounts on holiday homes in Heart of Chicago on Stayz, 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.
Can I change or cancel my Heart of Chicago holiday home booking on Stayz?
To find Heart of Chicago holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Heart of Chicago?
A long-stay holiday home in Heart of Chicago 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Heart of Chicago holiday home?
Book your Heart of Chicago holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Heart of Chicago?
Prices for holiday homes in Heart of Chicago 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Heart of Chicago to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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