Compare Vacation Rentals & Rent By Owner Homes in Heart of Chicago, Chicago, Illinois, USA
About Heart of Chicago Vacation Rentals
With more than 1497 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 781.94 ft² on average, with prices averaging US $376 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
Frequently Asked Questions About Heart of Chicago?
What are the top vacation rentals in Heart of Chicago?
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- 1F Chicago's Little italy Graystone nearDowntown
- Million Dollar Views! Luxury Downtown Skyhouse!
- Prime Location! Modern 3 Bed 3 Bath Rental in Chicago
- Cozy Pilsen Depa
- MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
- 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
- Family Friendly 2-Bedroom w/Kitchen & Laundry
- The Suite Spot Eclectic Modern Central Sleeps 6
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 1497 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 | 63 |
| University Village / Little Italy Vacation Rentals in Chicago, Illinois | 743 |
| Lower West Side Vacation Rentals in Chicago, Illinois | 909 |
| Pilsen Vacation Rentals in Chicago, Illinois | 3300 |
| McKinley Park Vacation Rentals in Chicago, Illinois | 739 |
