Heart of Chicago holiday lettings

We found 45 holiday rentals — enter your dates for availability

Discover a selection of 19 apartments 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.

Holiday rentals with weekly discounts - Heart of Chicago

Showing deals for:14 Nov - 21 Nov

Image gallery for Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

Property grounds
9.0 out of 10 rating
Wonderful
(7 reviews)

Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

Chicago, IL

7% off
Price is £1,004
£143 per night
includes taxes & fees
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

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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 around 30 available in vibrant neighbourhoods close to attractions like Millennium Park, the Art Institute of Chicago, and the iconic Magnificent Mile. These apartments typically come with modern amenities, including fully equipped kitchens, spacious living areas, and in many cases, stunning city views from large windows.
Are there any beach house rentals in Heart Of Chicago?
In the Heart of Chicago, there are several beach house rentals available, particularly along the shores of Lake Michigan. These properties are often found in vibrant neighbourhoods such as Lincoln Park and near the popular North Avenue Beach. Travellers can expect amenities like spacious living areas, fully equipped kitchens, and outdoor decks or patios for enjoying the lakeside views.
How much does it cost to rent a holiday home in Heart Of Chicago?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Heart Of Chicago 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 Heart Of Chicago holiday house rentals?
You can find great discounts on house rentals in Heart Of Chicago 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 Heart Of Chicago?
In the Heart of Chicago, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals conveniently. Many rentals also feature coffee and tea makers for a comforting start to the day. Onsite parking is available in several properties, which is quite advantageous in the bustling city. Additionally, outdoor spaces like patios and decks provide a pleasant setting for relaxation while enjoying the vibrant city atmosphere.
Are there any family house rentals in Heart Of Chicago?
In the Heart of Chicago, there are some family-friendly house rentals available, with around 21 options to choose from. This vibrant area is known for its cultural attractions and stunning architecture. Many of the properties offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play. Visitors can also expect amenities such as Wi-Fi and air conditioning to ensure a comfortable stay.
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 pools and hot tubs. This vibrant urban area offers a range of accommodation options, from luxurious apartments in high-rise buildings to charming townhouses in historic districts. Many of these rentals come equipped with amenities such as private hot tubs, shared pools, and outdoor terraces, superb for relaxing after a day of exploring the city's attractions.
Are there any Heart Of Chicago holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 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.
Are there pet-friendly holiday rentals in Heart Of Chicago?
In the Heart of Chicago, there are several pet-friendly holiday rentals available, providing a great base for exploring the vibrant city. Many of these accommodations come equipped with modern amenities such as fully stocked kitchens, free Wi-Fi, and spacious living areas, making them comfortable for both pets and their owners.
Can I find long-stay holiday rentals in Heart Of Chicago?
A long-stay holiday rental 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 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 Heart Of Chicago for a holiday rental?
The best time to visit the Heart of Chicago for a holiday rental is during the vibrant summer months, particularly in July. This period falls within the peak season, which runs from May to July, and is characterised by bustling streets filled with festival-goers, outdoor diners, and locals enjoying the city's many attractions. The warm weather, with temperatures typically reaching the high 20s Celsius, creates the great setting for exploring Chicago's stunning architecture and world-class museums.

Summer in Chicago offers an array of outdoor activities, from leisurely strolls along the picturesque Lakefront Trail to enjoying live music at the numerous summer festivals. Attractions like Millennium Park come alive with events and performances, making it a fantastic time to immerse yourself in the local culture.

For those seeking a more budget-friendly experience, consider visiting in November. While the summer crowds have dispersed, the city still offers a unique charm as it transitions into winter. You can enjoy a quieter atmosphere, explore the city's renowned shopping districts, and even catch the early festive decorations without the hustle and bustle of peak season.
Are there any remote work holiday rentals in Heart Of Chicago?
In the Heart of Chicago, there are numerous remote work holiday rentals available, with around 35 options to choose from. This vibrant area is well-suited for those looking to combine work and leisure, as many properties come equipped with essential amenities tailored for remote work. Travellers can expect features such as high-speed Wi-Fi, dedicated office spaces, desks, desk chairs, and even computer monitors in some rentals, ensuring a comfortable and productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Heart Of Chicago holiday rental?
Book your Heart Of Chicago 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 Heart Of Chicago?
In the Heart of Chicago, visitors can experience firsthand a variety of attractions that showcase the city's rich culture and vibrant atmosphere. The iconic Millennium Park is a must-visit, featuring the famous Cloud Gate sculpture, often referred to as "The Bean," and the beautiful Jay Pritzker Pavilion hosting various performances. Nearby, the Art Institute of Chicago offers an extensive collection of artwork, making it a prime destination for art lovers.

The Magnificent Mile, located just a short stroll away, is renowned for its upscale shopping and dining options, alongside impressive architecture. The historic Water Tower and the Chicago Riverwalk provide scenic spots for leisurely walks and stunning views of the skyline.
Can I change or cancel my Heart Of Chicago home rental booking on Vrbo?
To find Heart Of Chicago 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Heart Of Chicago 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.

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