Compare Vacation Rentals & Rent By Owner Homes in Second City, Chicago, Illinois, USA
About Second City Vacation Rentals
With more than 3979 Second City 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 Second City.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Second City, 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 Second City. Places to stay near Second City are 775.38 ft² on average, with prices averaging CA $569 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Second City with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Frequently Asked Questions About Second City?
What are the top vacation rentals in Second City?
- The Sono Chicago
- 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
- NEW LUXURY PENTHOUSE CONDO
- Magic Factory Loft 2West
- Single Family Home! Sleeps 8 Lincoln Park/Lakeview
- NEW LUXURY CONDO WITH PATIO DECK
How many Rentbyowner vacation rentals are available in Second City?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 3979 in the Second City 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 Second City.
Nearby Neighborhood (12)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1545 |
| The Loop Vacation Rentals in Chicago, Illinois | 713 |
| Near North Side Vacation Rentals in Chicago, Illinois | 619 |
| South Loop Vacation Rentals in Chicago, Illinois | 366 |
| River North Vacation Rentals in Chicago, Illinois | 332 |
| Lakeview Vacation Rentals in Chicago, Illinois | 266 |
| West Loop Vacation Rentals in Chicago, Illinois | 213 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 153 |
| Hyde Park Vacation Rentals in Chicago, Illinois | 103 |
| O'Hare Vacation Rentals in Chicago, Illinois | 50 |
| Gold Coast Vacation Rentals in Chicago, Illinois | 37 |
| Magnificent Mile Vacation Rentals in Chicago, Illinois | 3906 |
