Heart of Chicago vacation rentals

We found 50 vacation rentals — enter your dates for availability

Discover a selection of 22 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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Frequently asked questions

What is the most popular type of vacation rental accommodation in Heart of Chicago?
Apartments are the most popular kind of vacation rental in Heart of Chicago, according to our data. Even if you’ve got something bigger or smaller in mind, Vrbo has vacation homes in a variety of sizes and shapes. Browse our many options to find your perfect pad.
How much does it cost to rent a vacation rental in Heart of Chicago?
The average price for a vacation rental in Heart of Chicago is determined by a number of factors, such as property type, season and length of stay. Whether you’re in search of a villa with space for extended family or a quaint cottage for you and your other half, just enter your dates of travel to see stays with unbeatable value.
How much does it cost to rent a beach house in Heart of Chicago?
Prices for beach houses in Heart of Chicago may differ depending on the type and size of the property and when you’re traveling. Just enter your travel dates into Vrbo and the number of guests to view your rental options and prices. From there you can use our filters to tailor your search by amenities, nearby activities, ratings and more.
Are there pet-friendly vacation rentals in Heart of Chicago?
Happily, yes. Choose from eight stays that allow pets in Heart of Chicago on Vrbo. Our furry friends need a getaway too, so simply use our search function for pet-friendly vacation rentals to book a perfect pad where Spot can lap up the good times.
What are popular rental amenities in Heart of Chicago?
A nearby marina, a nearby casino and WiFi are rated the most popular rental amenities in Heart of Chicago. Whether you plan to go by yourself, with your sweetheart or a group of family members, Vrbo will help you find a vacation rental that fits your style with all the features you need.
Are there large group vacation rentals in Heart of Chicago?
With six Heart of Chicago vacation properties that can accommodate a group of five or more people, you can invite a few extra friends or family members along. Whether you’re planning a casual get-together or a special event, we’ll help you find the perfect space to match the occasion.
Are there vacation rentals in Heart of Chicago that welcome kids?
Bring the whole family together for an adventure in Heart of Chicago at one of our eight family-friendly properties. Lots of these stays offer conveniences that are perfect for getaways with the kids, like dining rooms, living rooms and swimming pools. Just click on the “Properties good for families” filter box and select your favorite.
Can I find two-bedroom vacation rentals in Heart of Chicago?
Take off with your besties and enjoy peace, privacy and comfort in one of the seven two-bedroom vacation homes Heart of Chicago has to offer.
Are there vacation rentals with WiFi in Heart of Chicago?
Whether you want to keep up with the headlines, check emails or post a pic to social media, there are six vacation homes with WiFi in Heart of Chicago. Check the “WiFi” box when searching on Vrbo and stay connected on your getaway.
How can I find vacation rentals with air conditioning in Heart of Chicago?
Heart of Chicago has eight vacation rentals where you can unwind in air-conditioned comfort. To find a stay on Vrbo with this perk, enter your travel dates and use the handy filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Heart of Chicago?
You should check with the Heart of Chicago vacation rental you want on Vrbo as age restrictions vary. However, normally it’s 16, 18 or 21.
How long can I rent a vacation rental in Heart of Chicago for?
The amount of time you can stay in a Heart of Chicago vacation home for is down to the property. Simply put in your dates of travel to see available options that offer extended stays. They feature all you require to make your extended getaway more enjoyable and comfortable, such as air conditioning and laundries. Some properties may also offer weekly or monthly discounted prices, so you can stay longer for less money.
Does Vrbo offer discounts for vacation homes in Heart of Chicago?
Whether you’ve got your eye on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some great deals and discounts on Vrbo. From short stays to extended getaways, we’ve got the ideal place for your next Heart of Chicago escape.

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