Find Vacation Rentals in Near South Side

We have 2,215 properties to choose from
Anytime
Guests
Anytime
Guests

Popular Near South Side Vacation Rentals

Find the perfect Near South Side vacation rental

Bed and breakfast Near South Side
from $362 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Suite, 1 King Bed (Sinclair)

4.9
Outstanding(166 ratings)
Near South Side, Chicago, Illinois, United States
HomeToGo
Details
Bed and breakfast Near South Side
from $363 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Suite, 1 King Bed (Everleigh)

4.9
Outstanding(166 ratings)
Near South Side, Chicago, Illinois, United States
HomeToGo
Details
Bed and breakfast Near South Side
from $309 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Carmen)

4.9
Outstanding(166 ratings)
Near South Side, Chicago, Illinois, United States
HomeToGo
Details
Bed and breakfast Near South Side
from $309 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Dybek)

4.9
Outstanding(166 ratings)
Near South Side, Chicago, Illinois, United States
HomeToGo
Details
Bed and breakfast Near South Side
from $242 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 Queen Bed (Second City)

4.9
Outstanding(166 ratings)
Near South Side, Chicago, Illinois, United States
HomeToGo
Details
Bed and breakfast Near South Side
from $309 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Harvey)

4.9
Outstanding(166 ratings)
Near South Side, Chicago, Illinois, United States
HomeToGo
Details
Bed and breakfast Near South Side
from $242 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 Queen Bed (Meno)

4.9
Outstanding(166 ratings)
Near South Side, Chicago, Illinois, United States
HomeToGo
Details
Bed and breakfast Near South Side
from $272 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Rooney)

4.9
Outstanding(166 ratings)
Near South Side, Chicago, Illinois, United States
HomeToGo
Details
Bed and breakfast Near South Side
from $276 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Room, 1 King Bed (Cisneros)

4.9
Outstanding(166 ratings)
Near South Side, Chicago, Illinois, United States
HomeToGo
Details
Show more

Vacation rentals with a balcony

Bed and breakfast  Near South Side
from $229 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Dubois Guest House Room 201

3.7
Good(3 ratings)
Near South Side, Chicago, Illinois, United States
Balcony
Vrbo
Details
Bed and breakfast  Near South Side
from $176 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Villa Dubois Guest Room 6

Near South Side, Chicago, Illinois, United States
Balcony
Vrbo
Details
Bed and breakfast  Near South Side
from $278 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Dubois Guest House Room 103

4.4
Very good(3 ratings)
Near South Side, Chicago, Illinois, United States
Balcony
Vrbo
Details
Show more

Vacation Homes With Terraces

Bed and breakfast  Near South Side
from $222 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Dubois Guest House Room 302

Near South Side, Chicago, Illinois, United States
Balcony/Patio
Vrbo
Details
Bed and breakfast  Near South Side
from $277 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Dubois Guest House Room 203

Near South Side, Chicago, Illinois, United States
Balcony/Patio
Vrbo
Details
Bed and breakfast  Near South Side
from $278 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Dubois Guest House Room 303

3.5
Good(4 ratings)
Near South Side, Chicago, Illinois, United States
Balcony/Patio
Vrbo
Details
Show more

Vacation rentals and apartments with air conditioning

Bed and breakfast  Near South Side
from $269 per night
Bed and breakfast ∙ 6 guests ∙ 1 bedroom

Just Minutes from Downtown Chicago

Near South Side, Chicago, Illinois, United States
Air conditioning
Agoda
Details
Bed and breakfast  Near South Side
from $107 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Chicago Downtown River North

Near South Side, Chicago, Illinois, United States
Air conditioning
Agoda
Details
Bed and breakfast  Near South Side
from $140 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Modern Shared Condo Near Downtown Chicago, Flexible Room Options and Shared Amenities

Near South Side, Chicago, Illinois, United States
Air conditioning
Agoda
Details
Show more

Frequently Asked Questions

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

In Near South Side, vacation rentals start at $92 per night.

Can I see all vacation rentals that are available in Near South Side?

You can find and compare 2,215 offers in Near South Side and book an ideal place for your next getaway.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Near South Side

Looking for a vacation rental in Near South Side? Tripping.com has 100 vacation rental homes available in Near South Side. You'll find 4 studios, 58 1-bedroom, 34 2-bedroom and 4 rentals with 3 or more bedrooms ranging from $43 a night. For extra convenience, many of these vacation homes can be booked directly online. The average price of a nightly rental in Near South Side is $249 while the average price of a weekly rental is $25. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Near South Side home is $25. Wondering if you can bring your dog or cat along with you? There are 6 pet-friendly vacation rentals available in Near South Side. In addition to accommodating pets, Near South Side rentals offer a variety of amenities. In particular, 81 rentals have Internet and WiFi, 79 have TV and/or cable and 18 have a pool or hot tub. Search properties from 5 vacation rental sites in Near South Side where the top providers in that area are HomeAway, Booking.com, and Expedia. There are 38 HomeAway rentals, 24 Booking.com short term rentals and 18 Expedia vacation rentals.

Popular Day Trips Near Near South Side

image-tag