Vacation Homes in South Side, IL
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top Vacation Homes in South Side

Cheerful 4 bedroom smart home w/ indoor fireplace

South Shore Retreat 5 bedrooms/entertainment

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Lakefront property , minutes from McCormick Place and Downtown Chicago.

“The Marlowe” A Couples Getaway

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

Huge Limestone SFH/McCormick

LakeHouse

House with garage, outdoor dining and basement bar
Top hotels in South Side

SpringHill Suites by Marriott Chicago Chinatown
Find the Best Vacation Homes in South Side
Why book a vacation home in South Side?
Vacation homes in South Side make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in South Side?
Private South Side rental homes range between $85 - $331 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in South Side vacation home rentals. You might look for South Side rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in South Side offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in South Side?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in South Side. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding South Side hotels and vacation homes that best suit your stay. We also have deals for flights, and South Side car rentals. You’ll save even more when you bundle your items into a South Side vacation package!
How many vacation homes are available to book in South Side?
There are 95 rental homes in South Side. Enter your travel dates to check availability.
How do I find the best price for a vacation home in South Side?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
South Side Vacation Homes essential information
Accommodation | 95 Vacation Homes |
---|---|
Lowest Price | $85 |
Highest Price | $331 |
Popular accommodation | Cheerful 4 bedroom smart home w/ indoor fireplace, South Shore Retreat 5 bedrooms/entertainment, Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago, 1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown, Lakefront property , minutes from McCormick Place and Downtown Chicago. , “The Marlowe” A Couples Getaway, Gorgeous historic mansion on UChicago campus. Renovation with original detail., LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins, Huge Limestone SFH/McCormick, LakeHouse, House with garage, outdoor dining and basement bar, Newly Revamped Home - For privacy lovers |
Explore more Vacation Homes
More places to stay in South Side
Most popular
- Hotels around Donald E. Stephens Convention Center
- Hotels around Water Tower Place
- Cheap Hotels in Chicago Union Station
- Hotels around Riviera Theatre
- Hotels around House of Blues Chicago
- 5 Star Hotels in North Suburbs
- Hotels around Anna and Frederick Douglass Park
- Hotels around Michigan Avenue
- Hotels around James M. Nederlander Theatre
- Hotels around Millennium Park
- Hotels around Lincoln Park Zoo
- Hotels around Grant Park
- Hotels around Aon Center
- Hotels around Allstate Arena
- Hotels around Rosemont Theatre
- Hotels around Chicago Theatre
- Hotels around Vic Theatre
- Hotels around Navy Pier
- Hotels around Wrigley Field
- Hotels around Credit Union 1 Arena
- Hotels around Wintrust Arena
- Hotels around Chicago Riverwalk
- Hotels around Bridgeport Art Center
- North Suburbs Luxury Hotels
- Hotels around United Center
- Hotels around Soldier Field
- Hotels around Rivers Casino
- Hotels around McCormick Place
- Hotels around Santa's Village