A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

South Side Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for South Side holiday rentals

Private kitchen

1. ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago

ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
Kenwood
10.0 out of 10, Exceptional, (4 reviews)
"Exactly as described, would recommend"
United States
Anonymous traveller
The price is HK$1,960
HK$4,866 total
includes taxes & fees
2 Sept - 3 Sept
ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago
Private kitchen

2. 3BR | Complete & Well-Located Apt in Hyde Park

3BR | Complete & Well-Located Apt in Hyde Park
Hyde Park
7.6 out of 10, Good, (5 reviews)
"Enjoyed our stay. Thank you"
United States
Nicolle C.
The price is HK$909
HK$2,149 total
includes taxes & fees
1 Sept - 2 Sept
3BR | Complete & Well-Located Apt in Hyde Park
Living area

3. Stylish 2BR Near Hyde Park, UChicago & Lake

Stylish 2BR Near Hyde Park, UChicago & Lake
Woodlawn
10.0 out of 10, Exceptional, (5 reviews)
"Definitely would rent again "
United States
Brittney J.
The price is HK$1,317
HK$3,241 total
includes taxes & fees
31 Aug - 1 Sept
Stylish 2BR Near Hyde Park, UChicago & Lake
Room

4. Group-Friendly 4BR Hyde Park Retreat Near UChicago

Group-Friendly 4BR Hyde Park Retreat Near UChicago
Hyde Park
6.0 out of 10, (5 reviews)
"Pretty standard for a VRBO property. No frills but excellent location and great that it had 4 bedrooms for our group. "
United States
Cuoghi E.
The price is HK$643
HK$2,698 total
includes taxes & fees
31 Aug - 1 Sept
Group-Friendly 4BR Hyde Park Retreat Near UChicago
Living area

5. Designer 3BR Near Beach & Obama Center

Designer 3BR Near Beach & Obama Center
Woodlawn
The price is HK$2,752
HK$6,408 total
includes taxes & fees
31 Aug - 1 Sept
Designer 3BR Near Beach & Obama Center
Games room

6. W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Brighton Park
9.4 out of 10, Exceptional, (12 reviews)
"It was great it had the basic amenities for a family to enjoy the stay"
United States
Damary T.
The price is HK$1,364
HK$3,068 total
includes taxes & fees
15 Sept - 16 Sept
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Living area

7. 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.
The price is HK$761
HK$2,033 total
includes taxes & fees
7 Sept - 8 Sept
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Room

8. Spacious Apt | 4 Queen Beds | Free Parking

Spacious Apt | 4 Queen Beds | Free Parking
Brighton Park
Spacious Apt | 4 Queen Beds | Free Parking
Living area

9. 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, (11 reviews)
"Cozy home, perfect for our stay. Highly recommend."
United States
Alisa G.
The price is HK$938
HK$2,111 total
includes taxes & fees
8 Sept - 9 Sept
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Private kitchen

10. Designer Home | Steps to the Obama Center & Beach

Designer Home | Steps to the Obama Center & Beach
Woodlawn
The price is HK$2,750
HK$8,054 total
includes taxes & fees
31 Aug - 1 Sept
Designer Home | Steps to the Obama Center & Beach
Room

11. Private Yard Near Beach & Obama Center

Private Yard Near Beach & Obama Center
Woodlawn
The price is HK$2,252
HK$6,338 total
includes taxes & fees
31 Aug - 1 Sept
Private Yard Near Beach & Obama Center
Exterior

12. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,289 reviews)
"Nice stay"
United States
Heather
The price is HK$1,193
HK$1,630 total
includes taxes & fees
31 Aug - 1 Sept
Sentral Michigan Avenue
Lake

13. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (23 reviews)
"Great location and super clean!"
United States
Erica
The price is HK$1,372
HK$2,097 total
includes taxes & fees
7 Sept - 8 Sept
Kasa Lake Shore Chicago
Private kitchen

14. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (520 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is HK$1,852
HK$2,368 total
includes taxes & fees
31 Aug - 1 Sept
Level Chicago – Old Town
Living area

15. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is HK$1,333
HK$1,768 total
includes taxes & fees
31 Aug - 1 Sept
LIVN Millennium Park Downtown Chicago 2BR
Room

16. Wabash 4BR - Pool, Free In & Out Parking 2

Wabash 4BR - Pool, Free In & Out Parking 2
Downtown Chicago
Wabash 4BR - Pool, Free In & Out Parking 2
Room

17. LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is HK$2,681
HK$3,622 total
includes taxes & fees
3 Sept - 4 Sept
LIVN West Loop Chicago King Studio
Interior

18. Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
9.6 out of 10, Exceptional, (8 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
The price is HK$1,968
HK$5,545 total
includes taxes & fees
2 Sept - 3 Sept
Modern West Loop Gem-City Views & Prime Location 3
Living area

19. River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.6 out of 10, Exceptional, (11 reviews)
"Excellent location. Host was very responsive. Check-in and parking was easy. The unit is very clean and uncluttered. Beds were comfortable."
United States
Kathleen M.
The price is HK$1,913
HK$4,078 total
includes taxes & fees
3 Sept - 4 Sept
River North Rooftop With In and Out Parking 1
Interior

20. Plymouth Collection: 3BD 2BA High Floor with Gym

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"The suite was excellent. Clean and very well furnished. The building is located within walking distance to many of the things that we did. We would stay in this place again in a heartbeat. Very pleased with our experience"
United States
Derek M.
Plymouth Collection: 3BD 2BA High Floor with Gym
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Side Hotel Reviews

Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"The room was very clean, the staff were very friendly and the breakfast was excellent!"
Gladys 2-night trip
Posted less than an hour ago
Hyatt Place Chicago-South/University Medical Center

Find out more about South Side

Search for holiday rentals in South Side on Expedia! You can easily find your home rentals, villas, holiday apartments in South Side using one of the methods below:

  • View our selection of featured holiday rentals in South Side
  • Use the map to find apartments and other holiday homes in the South Side neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in South Side while they last

Look no further and take a look at our great range of rental properties in South Side!

Explore a world of travel with Expedia