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

Search and Rent South Side Condos

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for South Side condo rentals

A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

1. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (65 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
$226 nightly
The price is $232
Sep 28 - Sep 29
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

2. Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.4 out of 10, Exceptional, (71 reviews)
"Easy access to the Green Line."
United States
Michael
$219 nightly
The price is $251
Sep 28 - Sep 29
Total with taxes and fees
Chic Suite/Mins to L Train /Laundry/Free Parking
A modern kitchen with stainless steel appliances, wooden cabinets, and a green tiled backsplash.

3. Wrigley Field MVP Suite 1 Bedroom Apartment

Wrigley Field MVP Suite 1 Bedroom Apartment
Lakeview
9.6 out of 10, Exceptional, (14 reviews)
"Great location. 30 steps to Wrigley field. Clean. Safe. Very clean apt."
United States
Curt M.
$540 nightly
The price is $666
Sep 27 - Sep 28
Total with taxes and fees
Wrigley Field MVP Suite 1 Bedroom Apartment
A hotel room with two beds, a desk, a chair, a TV, and a painting on the wall.

4. Chicago O’Hare Modern Hotel‑Style Stay w/parking

Chicago O’Hare Modern Hotel‑Style Stay w/parking
Norridge
$298 nightly
The price is $300
Sep 23 - Sep 24
Total with taxes and fees
Chicago O’Hare Modern Hotel‑Style Stay w/parking
A stone building with a covered entrance, benches, and potted plants.

5. Fully-Equipped Suite | Gym Access

Fully-Equipped Suite | Gym Access
York Center
10.0 out of 10, Exceptional, (1 review)
"Everything was nice. The breakfast was exceptional! Would definitely book again."
United States
Heather M.
$172 nightly
The price is $191
Sep 27 - Sep 28
Total with taxes and fees
Fully-Equipped Suite | Gym Access
A modern living room with a blue sofa, a round dining table, and a white desk.

6. MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking

MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
South Evanston
9.4 out of 10, Exceptional, (27 reviews)
"Parking was convenient and accommodations were comfortable."
United States
Evan Q.
$385 nightly
The price is $437
Sep 29 - Sep 30
Total with taxes and fees
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
A modern kitchen with white cabinetry, a stainless steel sink, a built-in oven, and a microwave.

7. Just remodeled apartment close to airport and mall

Just remodeled apartment close to airport and mall
Elk Grove Village
9.8 out of 10, Exceptional, (21 reviews)
"Great place! "
United States
Isabella T.
$259 nightly
The price is $277
Sep 24 - Sep 25
Total with taxes and fees
Just remodeled apartment close to airport and mall
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

8. Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort

Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
Downtown Evanston
10.0 out of 10, Exceptional, (37 reviews)
"Very nice place to stay with a great location. Thanks!"
United States
Robin M.
$371 nightly
The price is $421
Sep 23 - Sep 24
Total with taxes and fees
Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
A modern living room with a sofa, coffee table, and a kitchen area with a refrigerator and bar stools.

9. Wrigley Field All Star Suite 3 Bedrooms 2 Bath

Wrigley Field All Star Suite 3 Bedrooms 2 Bath
Lakeview
9.4 out of 10, Exceptional, (28 reviews)
"Perfect location! "
United States
Angela A.
$767 nightly
The price is $946
Sep 28 - Sep 29
Total with taxes and fees
Wrigley Field All Star Suite 3 Bedrooms 2 Bath
A modern living room with a grey sectional sofa, a black coffee table, and two framed pictures on the wall.

10. Cozy One Bedroom, Washer Dryer, Central Location, Fireplace, Monthly Discounts

Cozy One Bedroom, Washer Dryer, Central Location, Fireplace, Monthly Discounts
Lombard
9.4 out of 10, Exceptional, (23 reviews)
"The place was clean and wonderfull. Love the area."
United States
Jack W.
$339 nightly
The price is $359
Oct 5 - Oct 6
Total with taxes and fees
Cozy One Bedroom, Washer Dryer, Central Location, Fireplace, Monthly Discounts
A stone building with a covered entrance, benches, and potted plants.

11. Air-Conditioned King Suite | Complimentary Breakfast

Air-Conditioned King Suite | Complimentary Breakfast
York Center
8.8 out of 10, Excellent, (5 reviews)
"Sufficient for a quick overnight stay. Hotel was undergoing renovations."
United States
Anonymous traveler
$177 nightly
The price is $197
Sep 27 - Sep 28
Total with taxes and fees
Air-Conditioned King Suite | Complimentary Breakfast
A living room with a large arched window, a fireplace, and a sofa with patterned cushions.

12. Wrigley Field Home Run 4 Bedroom, 2 Bathroom

Wrigley Field Home Run 4 Bedroom, 2 Bathroom
Lakeview
9.8 out of 10, Exceptional, (21 reviews)
"Would definitely stay there again "
United States
Enrique
$879 nightly
The price is $1,085
Oct 5 - Oct 6
Total with taxes and fees
Wrigley Field Home Run 4 Bedroom, 2 Bathroom
A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

13. Free Breakfast. Indoor Pool. Gym. Business Center.

Free Breakfast. Indoor Pool. Gym. Business Center.
Schererville
$251 nightly
The price is $281
Oct 22 - Oct 23
Total with taxes and fees
Free Breakfast. Indoor Pool. Gym. Business Center.
A modern living room with a sofa, a coffee table, and a TV stand. A kitchen with a microwave, refrigerator, and bar stools is visible in the background.

14. Chicago's Hidden Treasure, "EVANSTON, IL"

Chicago's Hidden Treasure, "EVANSTON, IL"
Downtown Evanston
9.6 out of 10, Exceptional, (9 reviews)
"Great location for Northwestern. Clean,Safe place. "
United States
friendolyn
$371 nightly
The price is $421
Sep 23 - Sep 24
Total with taxes and fees
Chicago's Hidden Treasure, "EVANSTON, IL"
A modern living room with a sofa, a coffee table, and a TV stand. A kitchen with a microwave, refrigerator, and bar stools is visible in the background.

15. Half a mile from everything in the heart of Evanston, Illinois

Half a mile from everything in the heart of Evanston, Illinois
Downtown Evanston
10.0 out of 10, Exceptional, (12 reviews)
"Great place overall! The coffee machine on the 3rd floor was great to have. Beds comfortable."
United States
Lisa m.
$366 nightly
The price is $416
Sep 27 - Sep 28
Total with taxes and fees
Half a mile from everything in the heart of Evanston, Illinois
A stone building with a covered entrance, benches, and potted plants.

16. Fully-Equipped Suite | Complimentary Breakfast

Fully-Equipped Suite | Complimentary Breakfast
York Center
2.0 out of 10, (1 review)
"Hotel staff were great. “Suite” was a total disaster. Carpets were at least 10 years old with holes and furniture was as old and very uncomfortable. Never would have rented this “Suite” if we knew the true condition. Online pictures paint a very different picture."
United States
Paul S.
$170 nightly
The price is $189
Oct 4 - Oct 5
Total with taxes and fees
Fully-Equipped Suite | Complimentary Breakfast
A living room with a large arched window, a fireplace, and a sofa with patterned cushions.

17. Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom

Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
Lakeview
9.8 out of 10, Exceptional, (28 reviews)
"Location cannot be beat! So close to Wrigley and so fun! "
United States
Celia A
$880 nightly
The price is $1,086
Sep 27 - Sep 28
Total with taxes and fees
Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
A living room with a large arched window, a fireplace, and a sofa with patterned cushions.

18. Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms

Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
Lakeview
9.6 out of 10, Exceptional, (33 reviews)
"This place was perfect for our quick weekend getaway!"
United States
Kate P.
$880 nightly
The price is $1,086
Sep 27 - Sep 28
Total with taxes and fees
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
A modern kitchen with stainless steel appliances, a granite countertop, and a wine bottle.

19. Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms

Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
Lakeview
9.0 out of 10, Wonderful, (15 reviews)
"We loved the location and the VRBO itself. Clean, stocked with essentials, and easy to communicate with!"
United States
Meaghan M.
$880 nightly
The price is $1,086
Sep 27 - Sep 28
Total with taxes and fees
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
A hotel lobby with a stone fireplace, wooden flooring, and a seating area with chairs and a sofa.

20. 2 Bedroom | Free Daily Breakfast. Indoor Pool.

2 Bedroom | Free Daily Breakfast. Indoor Pool.
Schererville
$388 nightly
The price is $435
Oct 22 - Oct 23
Total with taxes and fees
2 Bedroom | Free Daily Breakfast. Indoor Pool.
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

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent
"amazing and friendly staff"
Amelia 2-night trip
Posted 8 hours ago
Holiday Inn Chicago – Midway Airport S by IHG

Find out more about South Side

South Side Condo Rentals information

Number of reviews
298
Accommodation
24 Condo Rentals
Lowest Price
$189
Highest Price
$1,086

Explore a world of travel with Expedia