Holiday Homes in Southwest Side

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Southwest Side holiday homes

Plymouth Collection: 3BD 2BA with Gym & Rooftop

Plymouth Collection: 3BD 2BA with Gym & Rooftop
Downtown Chicago
Plymouth Collection: 3BD 2BA with Gym & Rooftop

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.6 out of 10, Exceptional, (24 reviews)
"I had a fun stay "
United States
Jusu K.
The price is €157
includes taxes & fees
30 Apr - 1 May
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is €491
includes taxes & fees
27 Apr - 28 Apr
Near Lake and Museum • Modern • Game Area

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (63 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is €263
includes taxes & fees
27 Apr - 28 Apr
✽ Charming Cottage ✽ close to College/Town/Station

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very good, (23 reviews)
"Easy to access, big place, great for a group that needs to have several rooms and beds. Would definitely stay again"
United States
JOSE S.
The price is €258
includes taxes & fees
27 Apr - 28 Apr
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (60 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is €292
includes taxes & fees
10 May - 11 May
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (2 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is €325
includes taxes & fees
6 May - 7 May
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (44 reviews)
"Nice overall"
United States
Hell
The price is €267
includes taxes & fees
27 Apr - 28 Apr
LUXE 3 BR, 2 BA + Hot Tub

Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking

Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking
Bensenville
10.0 out of 10, Exceptional, (1 review)
"Easily the nicest place I have ever stayed at. Wonderful neighborhood, clean house, and great amenities. I’ll stay there again anyday. "
United States
Jacob F.
The price is €470
includes taxes & fees
29 Apr - 30 Apr
Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking

Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
Richton Park
9.0 out of 10, Wonderful, (24 reviews)
"The location was perfect! The house very spacious, with more than enough room for my boys!"
United States
Carmen
The price is €363
includes taxes & fees
29 Apr - 30 Apr
Spacious 3br home near Chicago, fenced yard for pets

PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
Lombard
9.6 out of 10, Exceptional, (18 reviews)
"Location was easy to find and good as a base for day trips to Chicago. "
United States
Brian H.
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

Spacious 5-bedroom bungalow with AC, WiFi in welcoming Berwyn

Spacious 5-bedroom bungalow with AC, WiFi in welcoming Berwyn
Berwyn
10.0 out of 10, Exceptional, (2 reviews)
"We had an excellent stay. Our host was responsive & accommodated an extremely early check-in request for us. This helped tremendously. Instructions were clear to get in & the home was spacious & clean. The location was great & easily accessible to restaurants. We would stay here again. "
United States
Sarah H.
Spacious 5-bedroom bungalow with AC, WiFi in welcoming Berwyn

Modern 4BR Retreat Near MDW | LCP Collection

Modern 4BR Retreat Near MDW | LCP Collection
Burbank
7.8 out of 10, Good, (8 reviews)
"Check in was easy and house was in safe neighborhood. It was a quick stay really a place to sleep for a few hours on our way through. "
United States
Stephanie S.
The price is €426
includes taxes & fees
29 Apr - 30 Apr
Modern 4BR Retreat Near MDW | LCP Collection

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Lockport
10.0 out of 10, Exceptional, (5 reviews)
"Everything was just as expected. Enjoyed our stay."
United States
Eileen W.
The price is €303
includes taxes & fees
30 Apr - 1 May
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie
10.0 out of 10, Exceptional, (36 reviews)
"Beautiful property, great location, quiet, with plenty of curb parking directly in front. "
United States
carlos l.
The price is €539
includes taxes & fees
28 Apr - 29 Apr
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Spacious 2BR Retreat • Full Basement • Coffee Bar • Pet Friendly

Spacious 2BR Retreat • Full Basement • Coffee Bar • Pet Friendly
Brookfield
Spacious 2BR Retreat • Full Basement • Coffee Bar • Pet Friendly

Wonderful in Wood Dale, right by O’Hare airport!

Wonderful in Wood Dale, right by O’Hare airport!
Wood Dale
10.0 out of 10, Exceptional, (18 reviews)
"Very clean, comfortable home in a good location. This was a great place to stay while visiting Chicago. "
United States
Pelayo M.
The price is €412
includes taxes & fees
30 Apr - 1 May
Wonderful in Wood Dale, right by O’Hare airport!

Entire home in Lockport, Illinois

Entire home in Lockport, Illinois
Lockport
10.0 out of 10, Exceptional, (1 review)
"The house is very clean. The host was very kind and responsive. "
United States
Susan B.
The price is €285
includes taxes & fees
27 Apr - 28 Apr
Entire home in Lockport, Illinois

Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
Game Room • Fire-pit • Playground • Gym • Billiard

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.6 out of 10, Exceptional, (28 reviews)
"Vic and his staff were extremely attentive. Thank you for a great stay"
United States
Brian N.
The price is €257
includes taxes & fees
30 Apr - 1 May
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Southwest Side Hotel Reviews

Find out more about Southwest Side

Southwest Side Holiday Homes information

Number of reviews
321
Accommodation
344 Holiday Homes
Lowest Price
€157
Highest Price
€539

Explore a world of travel with Expedia