Compare Vacation Rentals & Rent By Owner Homes in Heart of Chicago, Chicago, Illinois, USA
About Heart of Chicago Vacation Rentals
With more than 53 Heart of Chicago vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Heart of Chicago.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Heart of Chicago, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Heart of Chicago. Places to stay near Heart of Chicago are 906.16 ft² on average, with prices averaging US $304 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Heart of Chicago with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in Heart of Chicago, IL
Heart of Chicago Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Heart of Chicago?
- Charming Pilsen Studio - Quick Access to Downtown Chicago!
- Charming Chicago Apt
- 2-bedroom apartment in Pilsen
- Fresh Stylish Apartment
- Pet-Friendly Chicago Getaway w/Free Parking!
- Cozy Charming Art 🎨 Food🌮 Close to Train 🚉 Parking!
- Zen Oasis of Elegance: Expansive Executive Home
- Modern SFH Near McCormick Place & Soldier Field
- Charming Chicago Apt
- Luxuriant, Foodie, Culture,
How many Rentbyowner vacation rentals are available in Heart of Chicago?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 53 in the Heart of Chicago area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Heart of Chicago.
Nearby Neighborhood (5)
| Neighborhood | Property Count |
|---|---|
| Near West Side Vacation Rentals in Chicago, Illinois | 334 |
| University Village / Little Italy Vacation Rentals in Chicago, Illinois | 91 |
| Lower West Side Vacation Rentals in Chicago, Illinois | 44 |
| Pilsen Vacation Rentals in Chicago, Illinois | 3300 |
| McKinley Park Vacation Rentals in Chicago, Illinois | 739 |
