Compare Vacation Rentals & Rent By Owner Homes in The Loop, Chicago, Illinois, USA
About The Loop Vacation Rentals
With more than 1174 The Loop 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 The Loop.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner The Loop, 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 The Loop. Places to stay near The Loop are 608.1 ft² on average, with prices averaging R7,064 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in The Loop 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 The Loop, IL
Frequently Asked Questions About The Loop?
What are the top vacation rentals in The Loop?
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- 55th Floor Penthouse with Award-Winning Views
- 53 Floor MagMile Penthouse Views, Balcony, Pool
- 51st Floor MagMile Penthouse Views Balcony Pool
- 2-Story Penthouse Views, Fireplace, Pool, Gym
- Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
- 52nd Floor Penthouse with Skyline Views and Pool
- 50th Floor Mag Mile Views, Balcony, Pool, Gym
- Smart Home in Logan Square by the 606 Trail
- Tranquil Portage Park Stay
How many Rentbyowner vacation rentals are available in The Loop?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1174 in the The Loop 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 The Loop.
Nearby Neighborhood (10)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1327 |
| Near North Side Vacation Rentals in Chicago, Illinois | 564 |
| South Loop Vacation Rentals in Chicago, Illinois | 345 |
| River North Vacation Rentals in Chicago, Illinois | 338 |
| West Loop Vacation Rentals in Chicago, Illinois | 167 |
| West Loop Gate Vacation Rentals in Chicago, Illinois | 37 |
| Printers Row Vacation Rentals in Chicago, Illinois | 4031 |
| Lakeshore East Vacation Rentals in Chicago, Illinois | 3853 |
| Near East Side Vacation Rentals in Chicago, Illinois | 3849 |
| Chicago Museum Campus Vacation Rentals in Chicago, Illinois | 3309 |
