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Holiday Homes in Southwest Side

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Southwest Side holiday homes

1. 4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.4 out of 10, Exceptional, (25 reviews)
"Very clean, very quite loved having 3 bathrooms, had everything you’d need for your stay"
Canada
LM
The price is €695
includes taxes & fees
17 Sept - 18 Sept
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
A billiards room with multiple tables, large windows, and a high ceiling with exposed ductwork.

2. Wabash 4BR - Pool, Free In & Out Parking 1

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
The price is €901
includes taxes & fees
8 Oct - 9 Oct
Wabash 4BR - Pool, Free In & Out Parking 1
A wooden deck with a railing, a staircase, and a window with a wreath.

3. 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
9.8 out of 10, Exceptional, (34 reviews)
"I had a fun stay "
United States
Jusu K.
The price is €182
includes taxes & fees
29 Sept - 30 Sept
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

4. 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
7.8 out of 10, Good, (33 reviews)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing. Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix) All in all it was a good stay."
United States
Amal
The price is €270
includes taxes & fees
21 Sept - 22 Sept
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house. Lots of room and the games in the basement were awesome. Our grandsons loved them. The back yard is very nice too. The neighborhood is very nice. Everyone is so friendly. We had a great time."
United States
kim r.
The price is €491
includes taxes & fees
17 Sept - 18 Sept
Game Room • Fire-pit • Playground • Gym • Billiard
A living room with a sectional sofa, a round wooden coffee table, and three framed artworks on the wall.

6. 4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
10.0 out of 10, Exceptional, (6 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is €546
includes taxes & fees
21 Sept - 22 Sept
4BR Retreat w/ Theater, Arcade, Gym and Firepit
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

7. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
9.4 out of 10, Exceptional, (3 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is €206
includes taxes & fees
17 Oct - 18 Oct
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A circular fire pit with chairs around it, string lights overhead, and a house in the background.

8. Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater
Austin
6.0 out of 10, (1 review)
"Ok place to fit large families if no other option available. Not suitable for kids with allergies as there are some opportunities in the cleanness and maintenance of the property.The communication were ok for reserving but very limited during the stay.The floor os severely damaged as well."
United States
Adrian Cesar C.
Sleeps 18 • 7BR • Gym • Game Room • Theater
A modern living room with a sectional sofa, a coffee table, and a TV.

9. Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
8.6 out of 10, Excellent, (4 reviews)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
The price is €194
includes taxes & fees
29 Sept - 30 Sept
Attractive Coach House Apartment for rent in Oak Park.
A bedroom with a stone wall, a TV mounted on it, a bed with a white comforter, and a view of the outdoors through a window.

10. Beautifully furnished one bedroom loft located in Chicago's South side suburb

Beautifully furnished one bedroom loft located in Chicago's South side suburb
Hazel Green
The price is €302
includes taxes & fees
21 Sept - 22 Sept
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

11. PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.4 out of 10, Exceptional, (23 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is €383
includes taxes & fees
22 Sept - 23 Sept
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
A single-story house with a covered porch, a front door, and a small garden area.

12. 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, (3 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is €307
includes taxes & fees
6 Oct - 7 Oct
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

13. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
Forest Park
10.0 out of 10, Exceptional, (2 reviews)
"Great location, great place to stay, host was friendly. Parking was great. Hoping to be able to stay again in the near future."
United States
LEM R.
The price is €401
includes taxes & fees
29 Sept - 30 Sept
Classic Forest Park Foursquare < 1 Mi to Blue Line
A white two-story house with a porch, steps, and a small table with chairs.

14. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (33 reviews)
"Would stay there again"
United States
Margaret L.
The price is €530
includes taxes & fees
21 Sept - 22 Sept
Oak Park Victorian by FLW Studio
A hotel room with a large bed, two pillows, a teal throw blanket, and a view of buildings through a window.

15. 3BR · Steps from McCormick · Balcony & Gym

3BR · Steps from McCormick · Balcony & Gym
Near South Side
9.0 out of 10, Wonderful, (10 reviews)
"Six of us made a trip to Chicago and stayed at this location. The place is very roomy with a full kitchen. There was public transportation nearby to get us ro everywhere we were going ( Field museum, Grant park, Navy pier)."
United States
Kathy
3BR · Steps from McCormick · Balcony & Gym
A living room with a sofa, two armchairs, a coffee table, a flat-screen TV, and a painting on the wall.

16. Designer 3BR Near Beach & Obama Center

Designer 3BR Near Beach & Obama Center
Woodlawn
The price is €699
includes taxes & fees
29 Sept - 30 Sept
Designer 3BR Near Beach & Obama Center
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

17. Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (8 reviews)
"The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded promptly and was accommodating. Would book and recommend to others!"
United States
Ashley Y.
The price is €784
includes taxes & fees
21 Sept - 22 Sept
Sleeps 18 • 8BR • Game Room • Gym • Theater
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

18. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (58 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is €323
includes taxes & fees
21 Sept - 22 Sept
LUXE 3 BR, 2 BA + Hot Tub

19. Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
8.8 out of 10, Excellent, (3 reviews)
"Great home, clean ample space. Host was responsive and helpful. I would certainly stay again."
United States
Latasha C.
The price is €650
includes taxes & fees
22 Sept - 23 Sept
Arcade • Theater • Gym • Office • Sleeps 15
A modern gym with various exercise equipment, including a bench press, dumbbells, and a treadmill.

20. Brand New 12 Bedroom Mansion

Brand New 12 Bedroom Mansion
Downtown Chicago
The price is €3,455
includes taxes & fees
29 Sept - 30 Sept
Brand New 12 Bedroom Mansion
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 Southwest Side Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Comfortable and aesthetic! Enjoyed our stay a lot."
Ryan 4-night trip
Posted 4 hours ago
InterContinental Chicago Magnificent Mile by IHG

Find out more about Southwest Side

Southwest Side Holiday Homes information

Number of reviews
36,494
Accommodation
345 Holiday Homes
Lowest Price
€78
Highest Price
€376

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