South Side Vacation Rentals

Vacation Rentals in South Side

LakeHouse
10.0 out of 10, Exceptional, 7 reviews
"Great"
LakeHouse
cozy home in Bridgeport Chicago. walking to park and river front
10.0 out of 10, Exceptional, 1 review
"Staying at this VRBO house in Chicago was an absolute knockout! The location was perfect for catching the wrestling show with my friends, and the house itself was spacious, clean, and had all the amenities we needed. From comfy beds to a fully equipped kitchen, we felt right at home. The host was super accommodating and made check-in a breeze. Definitely a five-star experience – would book again in a heartbeat!"
cozy home in Bridgeport Chicago. walking to park and river front
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
9.8 out of 10, Exceptional, 60 reviews
"The location is perfect for plans to the museums and easy access to Lake Shore Drive. It also has plenty of street parking."
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
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Cheerful 4 bedroom smart home w/ indoor fireplace
7.4 out of 10, Good, 6 reviews
"The check in process was great and the house was very clean. It was easy to communicate with the property manager. Helped make our trip to chicago great!"
Cheerful 4 bedroom smart home w/ indoor fireplace
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, 429 reviews
"Nice place very nice front desk"
The price is $189
$251 total
includes taxes & fees
Jul 3 - Jul 4
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very Good, 94 reviews
"It was perfect for my needs for the week! Great area, right across the street from a park! Within walking distance/delivery distance to several dining options! Walking distance to Rush (about 20 minutes) & had 2 bike stations within a 10 minute walk in 2 different directions! Downside was it was near a train station so it was loud when you were outside but I could barely hear it when in the apartment. Plus there was construction going on so that added to the noise. Everything in the apartment...
The price is $100
$117 total
includes taxes & fees
Jun 30 - Jul 1
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, 311 reviews
"Pretty nice but the outlet and few other items not functioning "
The price is $189
$222 total
includes taxes & fees
Jul 2 - Jul 3
Sonder South Wabash
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, 250 reviews
"Had some difficulty finding a USB charging port. It was located under the kitchen counter-top."
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, 214 reviews
"The staff here is amazing and so helpful. Loved my stay here. "
The price is $244
$303 total
includes taxes & fees
Jun 30 - Jul 1
Level Chicago – Old Town
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, 132 reviews
"I loved my stay at Found Chicago! The logistical communication was easy to understand and implement, and I liked that it was contactless. It was nice to use my PIN code for room entrance instead of keeping track of a key. The WiFi was sufficient for remote meetings on my laptop. And all of the amenities (lobby access, luggage locker, and printer) were convenient and easy to use. I highly recommend this hotel, and I'll plan to stay here again. "
The price is $189
$222 total
includes taxes & fees
Jun 30 - Jul 1
Found Chicago powered by Sonder
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, 78 reviews
"I like the hotel, I did not realize there was no cleaning services or fresh towels. After 4 days the room needed some freshing and clean wash rags and towels. There was a washing machine but doing laundry on vacation is not for me."
The price is $235
$276 total
includes taxes & fees
Jun 30 - Jul 1
Sonder The Burnham
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, 34 reviews
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, 188 reviews
"Very nice property "
The price is $90
$95 total
includes taxes & fees
Jun 9 - Jun 10
WoodSpring Suites Chicago Addison
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, 68 reviews
"The building was clean and attractive. Security on site. Breakfast options close by. All the best sites walking distance. Units was amazing. Kasa very engaged and accessible. River Walk, boat excursions etc. Tours etc. Right there. Rooftop pool and all amenities on site wow!"
The price is $359
$421 total
includes taxes & fees
Jun 12 - Jun 13
Kasa River North Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very Good, 107 reviews
"Loved it "
The price is $191
$224 total
includes taxes & fees
Jul 7 - Jul 8
Sonder Jewelers Row
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, 162 reviews
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very Good, 68 reviews
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is $218
$256 total
includes taxes & fees
Jul 2 - Jul 3
Sonder The Plymouth
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, 107 reviews
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, 157 reviews
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, 40 reviews
"Well renovated, nice bathroom."
Wrigley/Southport Corridor Garden Oasis +parking!
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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.

Other types of properties in South Side you may be interested in

Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, 6,867 reviews
"Nice place."
The price is $167
$196 total
includes taxes & fees
Jun 16 - Jun 17
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.0 out of 10, Very Good, 2,372 reviews
"Very good location "
The price is $211
$247 total
includes taxes & fees
Jul 2 - Jul 3
Embassy Suites by Hilton Chicago Downtown River North
River Hotel
4.0 star property
8.8 out of 10, Excellent, 2,961 reviews
"Excellent property "
The price is $153
$180 total
includes taxes & fees
Jul 8 - Jul 9
River Hotel
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.

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 $90 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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