Compare Vacation Rentals & Rent By Owner Homes in Downtown Chicago, Chicago, Illinois, USA
About Downtown Chicago Vacation Rentals
With more than 2439 Downtown 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 Downtown Chicago.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Downtown 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 Downtown Chicago. Places to stay near Downtown Chicago are 693.86 ft² on average, with prices averaging US $434 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Downtown 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 Downtown Chicago, IL
Frequently Asked Questions About Downtown Chicago?
What are the top vacation rentals in Downtown Chicago?
- 52nd Floor MagMile Penthouse VIEWS Fireplace Pool
- 55-56 Mag Mile Penthouse
- 53 Floor MagMile Penthouse Views, Balcony, Pool
- 51st Floor MagMile Penthouse Views Balcony Pool
- 53/54 Mag Mile Penthouse VIEWS, Fireplace, Pool
- Magic Factory Loft 2West
- 51/52nd Floor Penthouse-VIEWS, Fireplace, Pool
- Magic Factory Loft 2East 4 Bd/3 Ba Families Groups
- Million Dollar Views! Luxury Downtown Skyhouse!
- Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
How many Rentbyowner vacation rentals are available in Downtown Chicago?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 2439 in the Downtown 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 Downtown Chicago.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| The Loop Vacation Rentals in Chicago, Illinois | 749 |
| Near North Side Vacation Rentals in Chicago, Illinois | 690 |
| South Loop Vacation Rentals in Chicago, Illinois | 368 |
| Near South Side Vacation Rentals in Chicago, Illinois | 357 |
| River North Vacation Rentals in Chicago, Illinois | 355 |
| Near West Side Vacation Rentals in Chicago, Illinois | 332 |
| West Town Vacation Rentals in Chicago, Illinois | 296 |
| Streeterville Vacation Rentals in Chicago, Illinois | 203 |
| West Loop Vacation Rentals in Chicago, Illinois | 200 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 154 |
| University Village / Little Italy Vacation Rentals in Chicago, Illinois | 88 |
| Old Town Vacation Rentals in Chicago, Illinois | 54 |
| River West Vacation Rentals in Chicago, Illinois | 50 |
| Gold Coast Vacation Rentals in Chicago, Illinois | 42 |
| Magnificent Mile Vacation Rentals in Chicago, Illinois | 4128 |
| Lakeshore East Vacation Rentals in Chicago, Illinois | 735 |
