Compare Vacation Rentals & Rent By Owner Homes in Chicago, Illinois, USA
About Chicago Vacation Rentals
With more than 7253 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 Chicago.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner 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 Chicago. Places to stay near Chicago are 740.57 ft² on average, with prices averaging US $361 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in 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 Chicago, IL
Chicago Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Chicago?
- The Sono Chicago
- 52nd Floor MagMile Penthouse VIEWS Fireplace Pool
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 55-56 Mag Mile Penthouse
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- 53 Floor MagMile Penthouse Views, Balcony, Pool
- Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
- 51st Floor MagMile Penthouse Views Balcony Pool
- 53/54 Mag Mile Penthouse VIEWS, Fireplace, Pool
- NEW LUXURY PENTHOUSE CONDO
How many Rentbyowner vacation rentals are available in Chicago?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 7253 in the 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 Chicago.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1531 |
| The Loop Vacation Rentals in Chicago, Illinois | 705 |
| Near North Side Vacation Rentals in Chicago, Illinois | 605 |
| South Loop Vacation Rentals in Chicago, Illinois | 369 |
| Near South Side Vacation Rentals in Chicago, Illinois | 356 |
| River North Vacation Rentals in Chicago, Illinois | 318 |
| Lakeview Vacation Rentals in Chicago, Illinois | 266 |
| West Loop Vacation Rentals in Chicago, Illinois | 221 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 152 |
| Hyde Park Vacation Rentals in Chicago, Illinois | 103 |
| Logan Square Vacation Rentals in Chicago, Illinois | 87 |
| Edgewater Vacation Rentals in Chicago, Illinois | 76 |
| Rogers Park Vacation Rentals in Chicago, Illinois | 69 |
| O'Hare Vacation Rentals in Chicago, Illinois | 51 |
| Wrigleyville Vacation Rentals in Chicago, Illinois | 50 |
| Wicker Park Vacation Rentals in Chicago, Illinois | 47 |
