Discover a selection of 1,000 vacation rentals in Near South Side, Chicago that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $59 per night, and condos 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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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, recognized for its lake, restaurants and sporting events. McCormick Place and Soldier Field are just a couple of the must-sees. If you're looking for accommodations 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 vacation home and experience everything that makes Near South Side a one-of-a-kind vacation spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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 center:

  • 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 center. 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 traveling 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.

How many vacation rentals are available around Near South Side, Chicago?

Our 2021 property listings offer a large selection of 762 vacation rentals around Near South Side. From 641 condo and apartment rentals to 53 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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

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

  • McCormick Place: 1,162 vacation rentals
  • Wintrust Arena: 1,428 vacation rentals
  • Chicago McCormick Place Station: 1,414 vacation rentals
  • Willie Dixon's Blues Heaven: 1,420 vacation rentals
  • Chicago 18th Street Station: 1,426 vacation rentals

But there are many other points of interest around Near South Side listed on Vrbo 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 Condos/Apartments in Near South Side?

Yes, of course. Vrbo has 641 Condos/Apartments in Near South Side. Our other popular types of vacation rentals in Near South Side include:

  • Houses: 53 rentals available
  • Studios: 616 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 148 vacation rentals with pool available in Near South Side. Please use our search bar to access the selection of vacation rentals available.