South Side Vacation Rentals
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Vacation Rentals in South Side
cozy home in Bridgeport Chicago. walking to park and river front
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
Cheerful 4 bedroom smart home w/ indoor fireplace
Sentral Michigan Avenue
Sonder Market Hall
Sonder South Wabash
Level Chicago – Old Town
Found Chicago powered by Sonder
Sonder The Burnham
The Neighborhood Hotel-Little Italy
WoodSpring Suites Chicago Addison
Kasa River North Chicago
Sonder Jewelers Row
Sonder The Plymouth
Walking distance to restaurants, shops and Lake Michigan,
Wrigley/Southport Corridor Garden Oasis +parking!
Other types of properties in South Side you may be interested in
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
River Hotel
Everything you need to know about South Side vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
South Side vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in South Side. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Side in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
How to find incredible deals on South Side rentals
At Expedia, we put the best South Side vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top South Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Side vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
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