Discover a selection of 1,000 holiday rentals in Near South Side, 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 pool and internet/WiFi. Prices start at £ 82 per night, and flats & apartments and houses are popular options for a stay in Near South Side. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Near South Side
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Destination guide

Delight in the lakeside landscape of Near South Side

Enjoy the museums and other features of Near South Side. This city is cosmopolitan and scenic, recognised for its lake, restaurants and sporting events. McCormick Place and Soldier Field are just a couple of the must-see attractions. 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.

Activities

Sightseeing in and around Near South Side

Do you want to find top things to see and do while you're in the area? Venture out of your holiday home and experience everything that makes Near South Side a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Skydeck Ledge (1.7 mi / 2.7 km)
  • John G. Shedd Aquarium (0.7 mi / 1.1 km)
  • Adler Planetarium and Astronomy Museum (0.9 mi / 1.4 km)
  • Navy Pier (2.4 mi / 3.9 km)
  • Lincoln Park Zoo (4.4 mi / 7.1 km)
  • Brookfield Zoo (11.2 mi / 18 km)
Natural features

Exploring the natural landscape of Near South Side

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Near South Side is a great place to get outside. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (1.7 mi / 2.8 km)
  • Grant Park (1.1 mi / 1.8 km)
  • Lincoln Park (6.5 mi / 10.5 km)
  • Northerly Island (0.6 mi / 0.9 km)
  • Northerly Island Park (0.7 mi / 1.1 km)
  • Lakefront Trail (1.4 mi / 2.3 km)
How to get there

How to get to and around Near South Side

Fly into Chicago, IL (MDW-Midway Intl.), the closest airport, located 7.9 mi (12.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Chicago, IL (ORD-O'Hare Intl.), which is 16.9 mi (27.1 km) away.

If you're travelling by train, make your way to Chicago 18th Street Station or Chicago McCormick Place Station and explore the city from there. You might consider catching a ride on the metro at Roosevelt Station for ease of access to the rest of the city.

Can I find a vacation rental around Near South Side?

Yes, our 2021 property listings offer a large selection of 793 vacation rentals near Near South Side. From 682 flats & apartments to 70 houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Near South Side for a holiday or a weekend are on Vrbo.

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

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

  • McCormick Place: 1,272 vacation rentals
  • Chicago McCormick Place Station: 1,534 vacation rentals
  • Wintrust Arena: 1,528 vacation rentals
  • Willie Dixon's Blues Heaven: 1,527 vacation rentals
  • Chicago 18th Street Station: 1,529 vacation rentals

But there are many other points of interest around Near South Side 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 Flats in Near South Side?

Yes, of course. Vrbo UK has 682 Flats in Near South Side. Our other popular types of vacation rentals in Near South Side include:

  • Houses: 70 rentals available
  • Studios: 584 rentals available
  • Townhouses: 7 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Hotels and more.

Can I find a vacation rental with pool in Near South Side?

Yes, you can select your preferred vacation rental with pool among our 197 vacation rentals with pool available in Near South Side. Please use our search bar to access the selection of vacation rentals available.