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South Side Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for South Side vacation rentals

Interior

2MI to Obama Center - Pet-Friendly near UOC!

2MI to Obama Center - Pet-Friendly near UOC!
Woodlawn
10.0 out of 10, Exceptional, (2 reviews)
"Great host very accommodating."
United States
Kali P.
2MI to Obama Center - Pet-Friendly near UOC!
TV

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Brighton Park
10.0 out of 10, Exceptional, (2 reviews)
"The rooms were spotless. The apartment was spacious. I enjoyed my stay. "
United States
Rachel
$292 nightly
The price is $326
Jul 28 - Jul 29
Total with taxes and fees
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Smart TV, fireplace, video games, DVD player

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax

Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Calumet Park
9.2 out of 10, Wonderful, (9 reviews)
"Lakeia was very accommodating throughout our stay."
United States
Timothy K.
$248 nightly
The price is $265
Jul 28 - Jul 29
Total with taxes and fees
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Smart TV, video games

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Excellent location and go anywhere so close."
United States
Yiu S.
$242 nightly
The price is $270
Jul 13 - Jul 14
Total with taxes and fees
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Room

King Bed | Smoking|Chicago

King Bed | Smoking|Chicago
Chatham
$167 nightly
The price is $202
Jul 6 - Jul 7
Total with taxes and fees
King Bed | Smoking|Chicago
Room

King Bed|Smoking|Chicago

King Bed|Smoking|Chicago
Woodlawn
$162 nightly
The price is $187
Jul 6 - Jul 7
Total with taxes and fees
King Bed|Smoking|Chicago
Smart TV, offices

Spacious 3BR · Bronzeville/South Loop · Sleeps 8

Spacious 3BR · Bronzeville/South Loop · Sleeps 8
Near South Side
9.0 out of 10, Wonderful, (4 reviews)
"Excellent stay! The property was clean and an easy walk to McCormick Place convention center. The space was colossal and well appointed, with soap and towels provided for the shower. We were greeted by a wonderful gentleman who took the time to explain the Chicago area to us. Checkout was a breeze—just had to leave our keys—and the instructions were very clear. There was only minimal housekeeping required before leaving the apartment. I would definitely stay here again"
United States
Ilir T.
$472 nightly
The price is $582
Jul 9 - Jul 10
Total with taxes and fees
Spacious 3BR · Bronzeville/South Loop · Sleeps 8
Room

Chicago|2 Full Bed|Smoking

Chicago|2 Full Bed|Smoking
Woodlawn
$175 nightly
The price is $203
Jul 15 - Jul 16
Total with taxes and fees
Chicago|2 Full Bed|Smoking
Individually decorated, individually furnished, iron/ironing board

Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
$301 nightly
The price is $358
Jul 7 - Jul 8
Total with taxes and fees
Kasa Lake Shore Chicago
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,200 reviews)
"Great location"
United States
JAVIER
$177 nightly
The price is $208
Jul 5 - Jul 6
Total with taxes and fees
Sentral Michigan Avenue
Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (14 reviews)
"The property was clean and the location was great."
United States
Steven C.
$488 nightly
The price is $602
Jul 8 - Jul 9
Total with taxes and fees
ENVITAE Hotel, 4BR Luxury Modern Apartments
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (497 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
$299 nightly
The price is $351
Jul 6 - Jul 7
Total with taxes and fees
Level Chicago – Old Town
TV, offices

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
$215 nightly
The price is $254
Jul 6 - Jul 7
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 2BR
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.2 out of 10, Wonderful, (9 reviews)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
$158 nightly
The price is $187
Jul 5 - Jul 6
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
$525 nightly
The price is $601
Jul 6 - Jul 7
Total with taxes and fees
River North Rooftop With In and Out Parking 3
Interior

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
$642 nightly
The price is $792
Jul 9 - Jul 10
Total with taxes and fees
Premium Urban 4BR - Perfect Mix of Comfort & Location
TV, offices

South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3
Downtown Chicago
8.8 out of 10, Excellent, (5 reviews)
"Clean place. Family friendly. Location was great. A lot of restaurants close by. Great communication from the host."
United States
jaspreet
$505 nightly
The price is $576
Aug 3 - Aug 4
Total with taxes and fees
South Loop Rooftop With In and Out Parking 3
Property grounds

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (84 reviews)
"Great location for a short trip "
United States
Eric W.
$278 nightly
The price is $343
Jul 5 - Jul 6
Total with taxes and fees
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (197 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
Kasa River North Chicago
TV, offices

Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2
Downtown Chicago
9.4 out of 10, Exceptional, (9 reviews)
"Excellent location, very clean & comfortable. West Loop is an awesome area to stay in Chicago. Seamless check in process."
United States
Dean R.
$814 nightly
The price is $934
Jul 9 - Jul 10
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 2
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Side Hotel Reviews

SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

10/10 Excellent
"Two nights stay. Two days parking. All good will stay again. A+ all the way."
kar 2-night trip
Posted 4 hours ago
SpringHill Suites by Marriott Chicago Chinatown

Find out more about South Side

Everything you need to know about South Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Side vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Side. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $478 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Side rentals

At Expedia, we put the best South Side vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top South Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Side vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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