Holiday Rentals in South Side

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Holiday Rentals in South Side

Our top choices for South Side holiday rentals

Cozy Studio in Hyde Park-Walk to Lake & University

10.0 out of 10, Exceptional, (2)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is €169
includes taxes & fees
8 Sept - 9 Sept
Cozy Studio in Hyde Park-Walk to Lake & University

Perfect 1BR Spot near Attractions

7.2 out of 10, Good, (5)
"Freshly painted and clean. Hosts were responsive. Everything we needed for our stay. Walkable area. "
The price is €178
includes taxes & fees
8 Sept - 9 Sept
Perfect 1BR Spot near Attractions

South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community

9.0 out of 10, Wonderful, (23)
"Very comfortable, enjoyed my stay "
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community

A Home Away From Home!

9.6 out of 10, Exceptional, (7)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!

LakeHouse

9.2 out of 10, Wonderful, (20)
"Everything was perfect with the property and the host even came to help right away when we had one issue with the lights."
LakeHouse

Comfortable Condo in the Heart of Bronzeville by RedAwning

6.6 out of 10, (4)
"There was confusion with VRBO regarding our arrival date, no fault of the property owner. They made arrangements to clean the unit and provide lunch for our group while we waited and offered a second night free for the inconvenience. Highly recommend. Property owner went above and beyond!"
The price is €354
includes taxes & fees
3 Sept - 4 Sept
Comfortable Condo in the Heart of Bronzeville by RedAwning

Come experience The Lake Shore!

10.0 out of 10, Exceptional, (1)
"We had a great stay at the property. "
Come experience The Lake Shore!

1 Mi to University of Chicago: Urban Escape!

10.0 out of 10, Exceptional, (7)
"Quiet area. The owner was very welcoming and we had a very pleasant stay. Place was spacious and clean"
1 Mi to University of Chicago: Urban Escape!

House with garage, outdoor dining and basement bar

7.4 out of 10, Good, (3)
"Property was very clean, warm and welcoming. Beds were comfortable. Property manager was great at checking in, and readily available. The place smells great! Everything is new! We will definitely book again!"
House with garage, outdoor dining and basement bar

Prime Spot, Chic 1-Bedroom Unit

5.0 out of 10, (2)
"This is exactly what we were looking for. Location is good near beautiful side streets and walking distance from shops and good restaurants. Very responsive host. Nice decorative touches and clean, efficient cooking area. Clean apartment which could use updating but if you want updates you’ll just have to pay more. This was our second stay in this general area and we liked this one better. Definitely a reasonable price for this area. Ad is accurate regarding the apartment. "
Prime Spot, Chic 1-Bedroom Unit

Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago

2.0 star property
9.6 out of 10, Exceptional, (10)
"Served us well for our event near the McCormick Center. Hospitality was second to none! "
Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago

Chic 1-bedroom apartment,15mims from downtown

9.0 out of 10, Wonderful, (2)
"Stayed here to work C2E2 for the weekend. Great big space with everything I needed to rest up after a long day of work."
Chic 1-bedroom apartment,15mims from downtown

Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago

8.6 out of 10, Excellent, (8)
"Very nice stay. Very clean, plenty of room, great location from Downtown Chicago. "
Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago

1-bedroom condo next to Chicago Midway International Airport

10.0 out of 10, Exceptional, (6)
"super nice place!"
1-bedroom condo next to Chicago Midway International Airport

Chic 1-bedroom apartment in marvelous Chicago with WiFi, AC.

Chic 1-bedroom apartment in marvelous Chicago with WiFi, AC.

Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront

10.0 out of 10, Exceptional, (2)
"Clean, comfortable, and quiet! We enjoyed the condo very much. "
Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront

Studio Apt Comfy & Sunlit

Studio Apt Comfy & Sunlit

Bronzeville Manor walking distance to hospitals

9.8 out of 10, Exceptional, (17)
"Great location, very clean place. Ample street parking and the owner is very nice. I’ll definitely be booking this location again."
Bronzeville Manor walking distance to hospitals

Explore Hyde Park: 2BR Apt on Blackstone Ave

The price is €193
includes taxes & fees
1 Sept - 2 Sept
Explore Hyde Park: 2BR Apt on Blackstone Ave
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

Find out more about South Side

Find out more about South Side

Everything you need to know about South Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

South Side holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Side holiday rentals we have selected for you start as low as €169 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Side rentals

At Expedia, we put the best South Side holiday 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 holiday.

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.