Discover a selection of 17 holiday rentals in South Shore, Chicago that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including internet/WiFi and air conditioning. Prices start at £ 69 per night, and houses and flats & apartments are popular options for a stay in South Shore. Either way, you'll find a rental for everyone's needs.
Destination guide

Explore the beachside setting in South Shore

The beaches and other outdoor surroundings create an inviting atmosphere in South Shore. This city's restaurants, shopping and golfing draw many visitors. McCormick Place and Willis Tower are just a couple of the must-see attractions in the area. If you're looking for accommodation options with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.


Sightseeing in and around South Shore

Do you want to find attractions to visit while you're in town? Venture out of your holiday home and experience everything that makes South Shore a fun spot to go on holiday. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Skydeck Ledge (8.9 mi / 14.3 km)
  • Adler Planetarium and Astronomy Museum (7.6 mi / 12.2 km)
  • John G. Shedd Aquarium (7.7 mi / 12.3 km)
  • Navy Pier (9.3 mi / 15 km)
  • Lincoln Park Zoo (11.5 mi / 18.5 km)
  • Brookfield Zoo (14.6 mi / 23.6 km)
Natural features

Exploring the natural landscape of South Shore

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in South Shore. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (8.9 mi / 14.3 km)
  • Grant Park (8.2 mi / 13.2 km)
  • Lincoln Park (13.6 mi / 21.9 km)
  • Jackson Park (1.5 mi / 2.4 km)
  • Osaka Garden (1.9 mi / 3.1 km)
  • Midway Plaisance (2.3 mi / 3.8 km)
How to get there

Transport options to and around South Shore

Fly into Chicago, IL (MDW-Midway Intl.), the closest airport, located 9.1 mi (14.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Chicago, IL (ORD-O'Hare Intl.), which is 22.9 mi (36.8 km) away.

If you're travelling by train, Chicago South Shore Station, Chicago Windsor Park Station and Chicago Bryn Mawr Station are the main stations in the area.

Can I find a vacation rental around South Shore?

Yes, our 2020 property listings offer a large selection of 17 vacation rentals near South Shore. From 8 houses to 8 flats & apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near South Shore for a holiday or a weekend are on Vrbo.

What is the best area to stay when traveling to South Shore?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in South Shore:

  • The Loop: 615 vacation rentals
  • Near North Side: 566 vacation rentals
  • West Town: 514 vacation rentals
  • Bucktown: 49 vacation rentals
  • Irving Park: 36 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to South Shore?

Vrbo UK offers a large selection of vacation rentals near lovely places in South Shore. From Vrbo UK travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Chicago 79th Street Station (Cheltenham): 1,327 vacation rentals
  • Chicago Stony Island Station: 1,305 vacation rentals
  • ETA Creative Arts Foundation: 1,301 vacation rentals
  • Chicago Windsor Park Station: 1,313 vacation rentals
  • Chicago South Shore Station: 1,312 vacation rentals

But there are many other points of interest around South Shore listed on Vrbo UK where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in South Shore?

Yes, of course. Vrbo UK has 8 Houses in South Shore. Our other popular types of vacation rentals in South Shore include:

  • Flats: 8 rentals available
  • Studios: 5 rentals available
  • House: 8 rentals available

Can I find a vacation rental with internet/wifi in South Shore?

Yes, you can select your preferred vacation rental with internet/wifi among our 12 vacation rentals with internet/wifi available in South Shore. Please use our search bar to access the selection of vacation rentals available.

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