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Heart of Chicago vacation rentals

We found 52 vacation rentals — enter your dates for availability

Discover a selection of 31 apartments and other vacation rentals in Heart of Chicago that are perfect for your trip. Vacation rentals offer the amenities you expect for your stay with friends, family, or just your pet, like WiFi and cable TV. You'll be sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

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Find out more about Heart of Chicago

Why visit Heart of Chicago

  • Family-friendly activities: Heart of Chicago offers numerous attractions perfect for family outings and adventures.
  • Cultural immersion: Experience the local atmosphere and friendly community while exploring historic buildings and urban parks.
  • Convenient transportation: The proximity to the CTA allows easy access to nearby attractions and neighborhoods.
  • Diverse accommodations: Choose from downtown apartments, cozy homes, or stylish condos to suit your vacation needs.
  • Outdoor experiences: Enjoy a perfect blend of city life with outdoor fun in this vibrant neighborhood.

Popular types of accommodation around Heart of Chicago

If you're exploring options for a vacation rental in the Heart of Chicago, you're in the right place. Our most sought-after accommodations include downtown Chicago apartments, cozy houses, and stylish condos. Whether you're looking for an affordable rental, a spacious bedroom apartment in the heart of the city, or even charming Oak Park apartments, we have a variety of choices to suit your needs and ensure a memorable stay.

  • Apartments: The top choice for travelers seeking a vacation rental in the Heart of Chicago, offering convenience and local amenities.
  • Houses: A popular option for groups or families wanting a home-like atmosphere during their stay.
  • Condos: A favored selection for those looking for modern living spaces with access to shared facilities.
  • Cottages: A charming choice for visitors seeking a cozy and unique retreat in the city.**

Top attractions near Heart of Chicago

Heart of Chicago is perfect for family outings and city-themed adventures, offering a range of attractions such as urban parks, historic buildings, and event venues. Visitors can immerse themselves in the local culture while enjoying outdoor experiences that cater to families and city explorers alike. Whether you're traveling solo or with loved ones, there's something for everyone to discover in this vibrant neighborhood.

  • McCormick Place: A premier convention center that offers a bustling business atmosphere, hosting a variety of events, exhibitions, and conferences. Its expansive space and modern facilities make it a hub for professionals and networking.
  • Grant Park: Often referred to as Chicago's Front Yard, this urban park features beautiful gardens, walking paths, and recreational areas, perfect for families and outdoor enthusiasts looking to enjoy the city's vibrant atmosphere.
  • Art Institute of Chicago: Renowned for its vast collection of artwork, this cultural gem showcases masterpieces from various periods, offering visitors an enriching experience in art and history.

Things to do recommended for couples

For a romantic getaway in the Heart of Chicago, enjoy live music at the House of Blues, savor a meal at the historic Michael Jordan Restaurant, or dance the night away at the Aragon Ballroom. Each offers a unique vibe for couples seeking a memorable experience.

Things to do recommended for families

Families visiting the Heart of Chicago can catch a game at iconic Wrigley Field, enjoy nature at the serene Northerly Island Natural Area, or unwind at The East Bank Club, all within a short drive, offering fun and relaxation for everyone.

Things to do recommended for groups

Experience the vibrant culture at the Chicago Theatre, just 4 miles away, or enjoy laughs at Second City, located 5 miles from Heart of Chicago. Don't miss shopping at Chicago Place Mall, also 4 miles away, perfect for family and business vibes.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Heart of Chicago

If you're traveling with a group, family, pets, or planning an extended stay, be sure to refine your search based on your top priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Heart of Chicago with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Heart of Chicago with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like private swimming pools. Additionally, looking at how close you are to family-friendly attractions is a smart move.
  • Taking your pets with you to Heart of Chicago: For many families, a vacation isn't truly a getaway without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and cozy beds to ensure that everyone feels at home.
  • Planning for a long term stay visiting Heart of Chicago: If you're searching for vacation 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 rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Heart of Chicago

Heart of Chicago is a vibrant neighborhood offering an ideal mix of family-friendly activities and urban charm. Visitors can explore charming estate homes and enjoy the local atmosphere filled with friendly people. Its proximity to the CTA makes it easy to navigate the city, allowing travelers to discover nearby attractions and other delightful neighborhoods. Experience the perfect blend of city life and outdoor fun in this welcoming area of Chicago.

  • Chicago: As one of the most iconic cities in the United States, Chicago offers a vibrant and diverse experience for travelers. Located in the Heart of Chicago, this city is known for its family-friendly activities, outdoor spaces, and rich cultural scene. Enjoy shopping at the Magnificent Mile or catch a game at one of the famous sports facilities. Don't miss the chance to explore the bustling tourist precincts filled with theaters and entertainment venues, where you can immerse yourself in the local culture while enjoying stunning views of the skyline.
  • Downtown Chicago: A mere 4 miles from the Heart of Chicago, Downtown Chicago is the bustling center of the city, perfect for exploration. Known for its family-oriented attractions, outdoor parks, and city-themed experiences, Downtown boasts a variety of shopping areas, theaters, and arena entertainment facilities. Visit the renowned tourist precincts and take in the sights of iconic stadiums and sports facilities. The vibrant atmosphere and endless options for dining and entertainment make Downtown Chicago a must-see destination for any visitor.
  • Lower West Side: Located just 0.1 miles away from the Heart of Chicago, the Lower West Side is a charming neighborhood that offers a unique blend of family activities, outdoor enjoyment, and vibrant city life. Ideal for a quick getaway, this area features arenas for entertainment, educational venues, and shopping areas. Explore its local landmarks, including stadiums and event conference venues, which are perfect for sports enthusiasts and event-goers alike. The Lower West Side promises an engaging experience that highlights the best of Chicago's culture and community.

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can change significantly. Additionally, extending your stay can lead to substantial savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform for you to plan new trips, keep your travel arrangements on track, or review and organize your reservations. Your saved and booked properties are conveniently categorized into Potential, Upcoming, and Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Heart Of Chicago?
In the Heart of Chicago, apartments are the most popular vacation rental option, with about 26 available throughout the area. These apartments are typically located in vibrant neighborhoods close to attractions like Millennium Park, the Art Institute of Chicago, and Navy Pier. Travelers can expect amenities such as fully equipped kitchens, modern living spaces, and often access to fitness centers or rooftop terraces for stunning city views. Additionally, there are several condos and vacation houses that provide more spacious rooms, making them ideal for families or groups looking for a home-like experience in the city.
Are there any beach house rentals in Heart Of Chicago?
In the Heart of Chicago, several beach house rentals are available, primarily located near popular waterfront areas such as Lake Michigan. These rentals often feature amenities like spacious living areas, fully equipped kitchens, and outdoor patios or balconies for enjoying the lake views. Travelers can expect to find comfortable accommodations that cater to families or groups, with some properties offering multiple bedrooms and easy access to nearby attractions like Navy Pier and the Chicago Riverwalk.
How much does it cost to rent a vacation home in Heart Of Chicago?
Prices for vacation 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 vacation 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, travelers can expect popular vacation rental amenities that enhance their stay. Most rentals feature fully equipped kitchens, allowing guests to prepare their own meals and enjoy the convenience of home dining. Additionally, many properties come with coffee and tea makers to kickstart the day. For those traveling by car, onsite parking is a significant advantage, making it easier to explore the city. Many rentals also include decks or patios, providing outdoor spaces to relax and take in the vibrant urban atmosphere.
Can I find family house rentals in Heart Of Chicago?
In the Heart of Chicago, there are approximately 15 family-friendly house rentals available, making it a great destination for families. Neighborhoods like Lincoln Park and Near North Side offer spacious homes with amenities ideal for travelers with children. Many of these properties feature inviting living rooms, fully equipped kitchens for preparing meals, and outdoor spaces where kids can play or relax.

Visitors can also enjoy close proximity to popular attractions such as the Lincoln Park Zoo, the Chicago Children's Museum, and the vibrant waterfront at Navy Pier. The area is well-connected, allowing easy access to public transportation, making it convenient for exploring the city's many cultural landmarks, parks, and dining options. See all family-friendly rentals in Heart Of Chicago.
Can I rent a vacation home with a pool or hot tub in Heart Of Chicago?
In the Heart of Chicago, travelers can find several vacation homes available for rent that feature hot tubs, making it an appealing destination for those looking to relax after exploring the city. Many of these properties are located in vibrant neighborhoods like River North and the Near North Side, where visitors can enjoy proximity to popular attractions, dining, and nightlife.

Expect a range of amenities in these rentals, including modern kitchens, spacious living areas, and outdoor spaces for entertaining. Some homes may also offer private hot tubs or access to shared amenities like rooftop terraces with stunning city views.
Are there any Heart Of Chicago vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Heart Of Chicago with parking available—perfect for families or travelers 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 vacation rentals in Heart Of Chicago?
In the Heart of Chicago, travelers can find several pet-friendly vacation rentals that offer a variety of amenities to ensure a comfortable stay. Many of these properties are equipped with modern kitchens, spacious living areas, and high-speed internet, making them ideal for both short and extended stays. The vibrant neighborhoods surrounding this area provide easy access to numerous parks, great for those traveling with pets.

For instance, Grant Park, situated nearby, is an expansive green space that features walking paths and beautiful gardens, allowing for enjoyable outings with your furry companions. Additionally, Lincoln Park, which is not far from the Heart of Chicago, includes pet-friendly cafes and shops, enhancing the overall experience for visitors with pets. See all pet-friendly rentals in Heart Of Chicago.
Can I find long-stay vacation rentals in Heart Of Chicago?
A long-stay vacation rental in Heart Of Chicago is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Heart Of Chicago for a vacation rental?
The peak season for visiting the Heart of Chicago typically spans from May to July, with July being the most popular month. This vibrant period attracts travelers eager to enjoy the city's bustling atmosphere, outdoor festivals, and numerous attractions. Visitors can experience firsthand the rich cultural scene, from music festivals to art fairs, all while taking advantage of the pleasant summer weather, which usually ranges from the low 60s to mid-80s Fahrenheit.

During these summer months, you'll find an abundance of outdoor activities and sightseeing opportunities. Stroll along the picturesque Lakefront Trail, explore Millennium Park, or indulge in the culinary delights of the city's renowned restaurants. The lively energy of fellow travelers and locals alike creates an unforgettable experience, making this an ideal time for those seeking to soak in the city's vibrant spirit.

For those looking for a more budget-friendly option, November offers a quieter atmosphere with fewer tourists. While the weather may be cooler, typically in the 30s to 50s Fahrenheit, this time of year provides a unique opportunity to explore the city's landmarks and enjoy cozy indoor experiences, such as visiting museums or enjoying a warm meal at a local eatery.

Ultimately, the best time to visit the Heart of Chicago depends on your preference for lively summer festivities or a more tranquil autumn experience.
Are there any remote work vacation rentals in Heart Of Chicago?
In the Heart of Chicago, there are numerous remote work-friendly vacation rentals available, with around 27 options to choose from. This vibrant area offers a mix of modern apartments and cozy condos, many of which come equipped with dedicated workspaces, including desks and ergonomic chairs, making them ideal for professionals needing to balance work and leisure. Travelers can expect high-speed internet access, often provided through a third-party service, ensuring seamless connectivity during their stay.

The Heart of Chicago is conveniently located near various points of interest, such as Millennium Park, the Art Institute of Chicago, and the Magnificent Mile, making it easy to explore the city's rich cultural offerings during downtime. Many rentals also feature amenities like fully equipped kitchens, allowing guests to prepare meals at their convenience, as well as comfortable living areas for unwinding after a productive day. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Heart Of Chicago vacation rental?
Book your Heart Of Chicago vacation 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 vacation 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, Illinois, United States of America?
In the Heart of Chicago, visitors can explore an abundance of attractions that showcase the city's vibrant culture and history. Millennium Park is a must-visit, featuring the iconic Cloud Gate sculpture, also known as "The Bean," and beautiful gardens. Just nearby, the Art Institute of Chicago offers an extensive collection of artwork, making it a key destination for art enthusiasts.

The Loop, which is part of the Heart of Chicago, is home to the historic Chicago Theatre and is a hub for theaters and shopping. The vibrant streets of State Street and Michigan Avenue, known as the Magnificent Mile, provide endless options for shopping, dining, and entertainment.

For those interested in architecture, a stroll along the Chicago Riverwalk offers stunning views of the city's towering skyscrapers and unique architectural styles. Additionally, Navy Pier, a short distance away, features attractions like the Ferris wheel, restaurants, and seasonal events, making it a lively spot for families and tourists alike.
Can I change or cancel my Heart Of Chicago home rental booking on Vrbo?
To find Heart Of Chicago vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 Heart Of Chicago vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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