Family-Friendly Vacation Rentals in West Englewood, IL: Compare 10+ Sites & Save

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  6.  West Englewood

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346 Best Family Vacation Rentals in West Englewood (Starting from $72)

Quiet 1BR, Eat-In Kitchen, Close to Midway
Quiet 1BR, Eat-In Kitchen, Close to Midway
Apartment
Chicago, IL, USA
3.2k from West Englewood center

Fireplace/Heating, Guest Services, Smoking, Parking, Pet Friendly, Air Conditioner, Internet

1 Bedroom4 Guests
8.0

Good

5 reviews

$171
Average price / night
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Close to Univ of Chicago - Extended Stays Welcome
Close to Univ of Chicago - Extended Stays Welcome
Apartment
Chicago, IL, 60621, United States
1.4k from West Englewood center

AC, Free Parking, Heater, Kitchen, Microwave, No Smoking, Toys, TV

3 Bedrooms6 Guests
New to Booking
$121
Average price / night
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Modern 1BR Outdoor Space & Cozy Vibes
Modern 1BR Outdoor Space & Cozy Vibes
Apartment
Chicago, IL, USA
3.2k from West Englewood center

Parking, Pet Friendly, Air Conditioner, Internet, View, Security/Safety, Child Friendly

1 Bedroom4 Guests
3.0

Review score

2 reviews

$72
Average price / night
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Charming 3-bed, 3-bath house in amazing Chicago, 10 min from Midway Airport.
Charming 3-bed, 3-bath house in amazing Chicago, 10 min from Midway Airport.
House
Chicago, IL, 60652, United States
2.7k from West Englewood center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$243
Average price / night
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Midway Hideaway -Cozy 1BR- parking
Midway Hideaway -Cozy 1BR- parking
Apartment
Chicago, IL, USA
3.2k from West Englewood center

Parking, Pet Friendly, Air Conditioner, Internet, Security/Safety, Child Friendly

1 Bedroom4 Guests
7.6

Good

6 reviews

$200
Average price / night
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2 Mi to Red Line: Chicago Home Near Sherman Park
2 Mi to Red Line: Chicago Home Near Sherman Park
House
Chicago, IL, 60609, United States
2.8k from West Englewood center

Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space, TV

5 Bedrooms9 Guests
New to Booking
$89
Average price / night
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BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12
BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12
House
Chicago, IL, USA
4.0k from West Englewood center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

5 Bedrooms12 Guests
9.3

Superb

3 reviews

$449
Average price / night
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Charming 2-bedroom apartment in awesome Chicago with WiFi, AC
Charming 2-bedroom apartment in awesome Chicago with WiFi, AC
Apartment
Chicago, IL, 60632, United States
3.2k from West Englewood center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$100
Average price / night
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Historic Feel Modern Comfort Walk to Parks & Food
Historic Feel Modern Comfort Walk to Parks & Food
Apartment
Chicago, IL, USA
4.0k from West Englewood center

Sports/Activities, Fireplace/Heating, View, Security/Safety, Parking, Guest Services, Internet

2 Bedrooms5 Guests
New to Booking
$117
Average price / night
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Your Home Away from home -12 mins from Downtown
Your Home Away from home -12 mins from Downtown
Apartment
Chicago, IL, 60609, United States
3.5k from West Englewood center

AC, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Toys

3 Bedrooms8 Guests
9.4

Superb

3 reviews

$328
Average price / night
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Entire Private Apartment, Near Downtown - Free Parking
Entire Private Apartment, Near Downtown - Free Parking
Apartment
Chicago, IL, USA
4.1k from West Englewood center

Apartments, Accommodations, Parking, Lodgings, Places to stay

4 Bedrooms12 Guests
New to Booking
$1000
Average price / night
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Cozy 2- bedroom w/ patio mins from Midway Airport
Cozy 2- bedroom w/ patio mins from Midway Airport
Apartment
Chicago, IL, 60629, United States
3.8k from West Englewood center

Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, Patio

9.8

Exceptional

12 reviews

$205
Average price / night
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Spacious 3BDR Luxury Penthouse
Spacious 3BDR Luxury Penthouse
Apartment
Chicago, IL, USA
4.1k from West Englewood center

Guest Services, Parking, Internet, Fireplace/Heating, Security/Safety, Air Conditioner, Child Friendly

3 Bedrooms6 Guests
New to Booking
$383
Average price / night
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Luxury suite with 3 Bedrooms \n10 min to downtown \n5 min to university of Chicago
Luxury suite with 3 Bedrooms \n10 min to downtown \n5 min to university of Chicago
Apartment
Chicago, IL, 60637, United States
4.2k from West Englewood center

AC, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
New to Booking
$252
Average price / night
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Exec Lux home wth 3 Level,6 Bdrms/3bth & 2 Kitchen
Exec Lux home wth 3 Level,6 Bdrms/3bth & 2 Kitchen
Apartment
Chicago, IL, USA
4.2k from West Englewood center

Internet, Air Conditioner, Child Friendly, Laundry, Smoking, Parking, Balcony/Terrace

6 Bedrooms9 Guests
10.0

Exceptional

1 reviews

$377
Average price / night
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Scott House in Woodlawn - Entire Building - includes basement space
Scott House in Woodlawn - Entire Building - includes basement space
House
Chicago, IL, 60637, United States
4.8k from West Englewood center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms5 Guests
7.8

Good

6 reviews

$184
Average price / night
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7 Mi to Downtown Luxe Chicago Condo
7 Mi to Downtown Luxe Chicago Condo
Apartment
Chicago, IL, USA
4.2k from West Englewood center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Condos

3 Bedrooms7 Guests
9.2

Superb

5 reviews

$513
Average price / night
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Stylish comfortable 3BR with tons of natural light
Stylish comfortable 3BR with tons of natural light
Apartment
Chicago, IL, 60632, United States
4.8k from West Englewood center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$229
Average price / night
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Shared, spacious condo near UChicago and Obama Center
Shared, spacious condo near UChicago and Obama Center
House
Chicago, IL, USA
4.4k from West Englewood center

Sports/Activities, Tv, View, Air Conditioner, Parking, Internet, Fireplace/Heating

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$107
Average price / night
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LUXE Vintage Loft, 10min to Downtown, Retro Movie Theatre - 15% Discount Applied
LUXE Vintage Loft, 10min to Downtown, Retro Movie Theatre - 15% Discount Applied
Apartment
Chicago, IL, 60609, United States
4.9k from West Englewood center

AC, Arcade, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms10 Guests
8.8

Fabulous

8 reviews

$547
Average price / night
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Chateau de Woodlawn - Peaceful 3 bedroom apartment.
Chateau de Woodlawn - Peaceful 3 bedroom apartment.
Apartment
Chicago, IL, USA
4.5k from West Englewood center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Self-catering, Accessible hotels

3 Bedrooms6 Guests
8.2

Very Good

11 reviews

$126
Average price / night
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Modern Chicago Getaway • Sleeps 6 • Near Downtown
Modern Chicago Getaway • Sleeps 6 • Near Downtown
Apartment
Chicago, IL, 60615, United States
5.1k from West Englewood center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
8.8

Fabulous

15 reviews

$364
Average price / night
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Luxurious 3Br with parking on premises 🌔
Luxurious 3Br with parking on premises 🌔
Apartment
Chicago, IL, 60632, United States
5.1k from West Englewood center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
9.2

Superb

14 reviews

$225
Average price / night
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Luxury Hyde Park Haven- Perfect for families and digital nomads.  Pet Friendly.
Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
House
Chicago, IL, 60615, United States
5.5k from West Englewood center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

4 Bedrooms8 Guests
9.8

Exceptional

17 reviews

$666
Average price / night
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The MOD Suite: Quaint family abode near UChicago, Lakeshore Dr. & DuSable Museum
The MOD Suite: Quaint family abode near UChicago, Lakeshore Dr. & DuSable Museum
Apartment
Chicago, IL, 60637, United States
5.9k from West Englewood center

AC, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
New to Booking
$146
Average price / night
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Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
House
Chicago, IL, 60653, United States
6.0k from West Englewood center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

6 Bedrooms15 Guests
9.2

Superb

22 reviews

$805
Average price / night
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Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
House
Chicago, IL, 60615, United States
6.2k from West Englewood center

AC, Barbecue, Crib, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry

5 Bedrooms8 Guests
10.0

Exceptional

17 reviews

$709
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in West Englewood.

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West Englewood Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 346 verified family-friendly vacation rentals in West Englewood. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in West Englewood vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $72 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in West Englewood offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in West Englewood are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in West Englewood often include amenities such as Child Friendly, Fireplace/Heating, and Internet. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.