South Side Vacation Rentals, Chicago: house rentals & more

Find the best place to stay - South Side

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Sleeps 4 · 1 bedroom · 1 bathroom

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Sleeps 20 · 5 bedrooms · 2+ bathrooms

Find spaces that suit your style

Find properties near top attractions in South Side

Wrigley Field

Top rated rentals - South Side

Fantastic Condo

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
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Explore the lakeside setting in South Side

Come and experience South Side and its museums, architecture and art galleries. Well-liked for its skyscrapers, aquarium and lake, this city is both cosmopolitan and scenic. Take in top local attractions like McCormick Place and Lake Michigan. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around South Side

Are you hoping to find things to do during your stay? Venture out of your vacation home and check out everything that makes South Side a fun spot to vacation. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

Lincoln Park Zoo (8.1 mi / 13 km)
Galloping Ghost (12.7 mi / 20.5 km)
The Dome at the Parkway Bank Sports Complex (18.3 mi / 29.4 km)
Adagio Teas (19.2 mi / 30.9 km)
Cog Hill Golf & Country Club (19.9 mi / 32.1 km)
Orland Park Sportsplex (20.5 mi / 32.9 km)

Exploring the natural landscape of South Side

Whether you're an active traveler or just want to spend some time taking in the scenery, South Side is a great place to get out in nature. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city center:

Grant Park (4.7 mi / 7.6 km)
Millennium Park (5.4 mi / 8.7 km)
Jackson Park (2.4 mi / 3.9 km)
Lakefront Trail (2.6 mi / 4.2 km)
Maggie Daley Park (5.4 mi / 8.7 km)
Ohio Street Beach (6.1 mi / 9.8 km)

Traveling to and around South Side

The nearest airport is in Chicago Midway Airport (MDW), located 6.9 mi (11.1 km) from the city center.

If you prefer to travel by train, Chicago 47th Street Station (Kenwood), Chicago 51st-53rd Street Station (Hyde Park) and Chicago 55th-56th-57th Street Station are the main stations that serve the city. It's easy to get around South Side by jumping on the metro at 51st Station, 47th Station (Green Line) or Garfield Station (Green Line).

Frequently asked questions

What is the best area to stay in South Side when booking a vacation rental?

Among the more desired neighborhoods to find a South Side vacation home is Essex. When you book your Vrbo vacation property, you'll have the entire place to yourselves. So you won't have to share it with anybody other than your group.

What is the most popular type of vacation rental accommodation in South Side?

Apartments are the most popular kind of vacation rental in South Side, according to our data. Even if you have a different idea about what you'd like, Vrbo has vacation homes in a variety of shapes and sizes. Browse our options to find your ideal fit.

How much does it cost to rent a vacation rental in South Side?

Several factors affect how much you pay for a vacation rental in South Side, including the type of property, length of stay and season. Still, all of our vacation homes have something in common — incredible value. Simply enter your travel dates to find your ideal match.

How much does it cost to rent a beach house in South Side?

When you travel and the style and size of the property will determine the cost of your beachside escape. Enter your South Side travel dates to view your available options on Vrbo. Did someone just say "private pool"? Use our filters to select the amenities and features you need.

What are popular rental amenities in South Side?

When it comes to rental amenities that people look for in South Side, a microwave oven, a fridge and a dryer are at the top of the list. With Vrbo vacation homes, you'll enjoy choices to fit your taste and style, whether you're taking a trip with relatives, friends or even pets.

Are there large group vacation rentals in South Side?

You can pick from 14 vacation properties in South Side that can accommodate 10 or more guests. Whether you're planning a family trip or a special event, there's plenty of room to get your group together under the same roof.

What are the top attractions for families in South Side?

Keep the kids busy at these fun family-friendly attractions in South Side:

Jackson Park
Guaranteed Rate Field
Abbott Park

Can I find two-bedroom vacation rentals in South Side?

Select from 26 two-bedroom rentals in South Side. Put the kids in the second room or fill it with a couple of your best friends. There's a comfy spot for whoever's lucky enough to be joining in on the fun.

Are there vacation rentals with WiFi in South Side?

South Side has 105 vacation rentals with WiFi, so you can stay connected during your trip. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming TV shows with the family to catching up on social media, these Vrbo homes will keep you online.

How old do you have to be to rent a vacation rental in South Side?

The minimum required age is normally 16, 18 or 21. It can change between properties on Vrbo, so look at the rules of your chosen South Side stay before you book.

How long can I rent a vacation rental in South Side for?

The amount of time you can book a South Side vacation home for depends on each property. Simply put in your travel dates to browse available options offering longer term stays. They have all you need to make your extended vacation more enjoyable and convenient, like air conditioning and kitchens. Some properties may also offer weekly or monthly discounted prices, so you can stay even longer for less.