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

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507 Best Family Vacation Rentals in Cragin (Starting from $110)

1BR 1BA Windy City Hideout - Lockwood rep
1BR 1BA Windy City Hideout - Lockwood rep
Apartment
Chicago, IL, USA
0.3k from Cragin center

Air Conditioner, Internet, Fireplace/Heating, Security/Safety, Child Friendly

2 Bedrooms2 Guests
New to Booking
$221
Average price / night
Check Availability
 3-bedroom apt .on North Side! Great location between downtown and the airport.
3-bedroom apt .on North Side! Great location between downtown and the airport.
Apartment
Chicago, IL, 60641, United States
0.6k from Cragin center

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

3 Bedrooms5 Guests
8.0

Good

4 reviews

$211
Average price / night
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2BR w Workspace and Coffee Bar Near Transit
2BR w Workspace and Coffee Bar Near Transit
Apartment
Chicago, IL, USA
0.6k from Cragin center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay

2 Bedrooms5 Guests
New to Booking
$296
Average price / night
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Updated Chicago Bungalow on a Beautiful and Calm Neighborhood Greenway Boulevard
Updated Chicago Bungalow on a Beautiful and Calm Neighborhood Greenway Boulevard
House
Chicago, IL, 60639, United States
1.0k from Cragin center

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

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$364
Average price / night
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2BR Travelers Favorite Modern
2BR Travelers Favorite Modern
House
Chicago, IL, USA
0.6k from Cragin center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

2 Bedrooms5 Guests
New to Booking
$280
Average price / night
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Luxury 5Bed 2Bath Apt w/Parking
Luxury 5Bed 2Bath Apt w/Parking
Apartment
Chicago, IL, 60641, United States
1.0k from Cragin center

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

4 Bedrooms8 Guests
7.6

Good

8 reviews

$549
Average price / night
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1BR Airy Apartment with Wi-Fi - Barry 2
1BR Airy Apartment with Wi-Fi - Barry 2
Apartment
Chicago, IL, USA
1.0k from Cragin center

Internet, Air Conditioner, Security/Safety, Guest Services, Child Friendly

1 Bedroom2 Guests
7.0

Good

1 reviews

$203
Average price / night
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Gorgeous 7BD Home w/ Garage
Gorgeous 7BD Home w/ Garage
House
Chicago, IL, 60641, United States
1.0k from Cragin center

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

8.8

Fabulous

6 reviews

$774
Average price / night
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ONE ROOM in AN APT HAVEN
ONE ROOM in AN APT HAVEN
Apartment
Chicago, IL, USA
1.3k from Cragin center

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

2 Bedrooms5 Guests
6.3

Good

3 reviews

$208
Average price / night
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Historic 1920s Private Bungalow Near Logan Square!
Historic 1920s Private Bungalow Near Logan Square!
House
Chicago, IL, 60641, United States
1.6k from Cragin center

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

4 Bedrooms8 Guests
9.8

Exceptional

40 reviews

$476
Average price / night
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Game Room, Firepit, Playground, Gym, Billiard
Game Room, Firepit, Playground, Gym, Billiard
House
Chicago, IL, USA
1.5k from Cragin center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms16 Guests
New to Booking
$1399
Average price / night
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Chic 3BR King Bed+Work-Friendly+ Firepit
Chic 3BR King Bed+Work-Friendly+ Firepit
House
Chicago, IL, 60641, United States
2.0k from Cragin center

AC, Barbecue, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
8.8

Fabulous

3 reviews

$455
Average price / night
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2BR Stylish Apartment in Avondale close to Shops - Roscoe 1W
2BR Stylish Apartment in Avondale close to Shops - Roscoe 1W
Apartment
Chicago, IL, USA
2.8k from Cragin center

Apartments, Cheap, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Self-catering

2 Bedrooms4 Guests
9.2

Superb

4 reviews

$243
Average price / night
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Stylish 3Bedroom Aparment w/Games & Free Parking
Stylish 3Bedroom Aparment w/Games & Free Parking
Apartment
Chicago, IL, 60639, United States
2.3k from Cragin center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet

3 Bedrooms6 Guests
9.4

Superb

3 reviews

$286
Average price / night
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Chic & Fully Furnished 2BR Apartment - Roscoe 1
Chic & Fully Furnished 2BR Apartment - Roscoe 1
Apartment
Chicago, IL, USA
2.9k from Cragin center

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

2 Bedrooms4 Guests
9.7

Exceptional

3 reviews

$345
Average price / night
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Modern 3-Bed Stay w/ Patio, Firepit, & Garage Parking Spot
Modern 3-Bed Stay w/ Patio, Firepit, & Garage Parking Spot
Apartment
Chicago, IL, 60647, United States
2.3k from Cragin center

AC, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$492
Average price / night
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Radiant 2BR Apt near Shops - Springfield 04-2
Radiant 2BR Apt near Shops - Springfield 04-2
Apartment
Chicago, IL, USA
2.9k from Cragin center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$258
Average price / night
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Cozy 3BR Apt w/ Park Views, Backyard, & BBQ!
Cozy 3BR Apt w/ Park Views, Backyard, & BBQ!
Apartment
Chicago, IL, 60647, United States
2.5k from Cragin center

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

3 Bedrooms6 Guests
New to Booking
$110
Average price / night
Check Availability
Relaxing 3BR Apt with King Beds & Washer - Lawndale 1 & 2 rep
Relaxing 3BR Apt with King Beds & Washer - Lawndale 1 & 2 rep
Apartment
Chicago, IL, USA
3.0k from Cragin center

Security/Safety, Air Conditioner, Guest Services, Internet, Child Friendly

3 Bedrooms6 Guests
1.0

Review score

1 reviews

$704
Average price / night
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Large 3BR /2BA Duplex• King • Parking
Large 3BR /2BA Duplex• King • Parking
Apartment
Chicago, IL, 60618, United States
2.6k from Cragin center

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

3 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$745
Average price / night
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Logan Sq 4BR Duplex • Garage • Sleeps 8
Logan Sq 4BR Duplex • Garage • Sleeps 8
Apartment
Chicago, IL, 60618, United States
2.6k from Cragin center

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

4 Bedrooms8 Guests
New to Booking
$717
Average price / night
Check Availability
Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!
Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!
Apartment
Chicago, IL, 60647, United States
2.6k from Cragin center

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

3 Bedrooms6 Guests
9.8

Exceptional

43 reviews

$379
Average price / night
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Bright Upper-Level 3BR Chicago • King • Walkable
Bright Upper-Level 3BR Chicago • King • Walkable
Apartment
Chicago, IL, 60618, United States
2.6k from Cragin center

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

3 Bedrooms5 Guests
10.0

Exceptional

18 reviews

$610
Average price / night
Check Availability
Historic North Side house w/ hot tub, public transit hub near downtown & Wrigley
Historic North Side house w/ hot tub, public transit hub near downtown & Wrigley
House
Chicago, IL, 60641, United States
2.8k from Cragin center

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

3 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$617
Average price / night
Check Availability
Family-friendly, stylish Chicago Apartment in Logan Square
Family-friendly, stylish Chicago Apartment in Logan Square
Apartment
Chicago, IL, 60647, United States
2.9k from Cragin center

AC, Arcade, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

3 Bedrooms7 Guests
10.0

Exceptional

67 reviews

$336
Average price / night
Check Availability
BoHo House - A Chic, 1903 Chicago Workers Cottage
BoHo House - A Chic, 1903 Chicago Workers Cottage
House
Chicago, IL, 60618, United States
3.0k from Cragin center

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

3 Bedrooms8 Guests
10.0

Exceptional

19 reviews

$641
Average price / night
Check Availability
Enjoy Chicago/suburbs 2BR townhouse fully equipped
Enjoy Chicago/suburbs 2BR townhouse fully equipped
House
Chicago, IL, 60707, United States
3.2k from Cragin center

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

2 Bedrooms6 Guests
10.0

Exceptional

14 reviews

$328
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 Cragin.

Stay Near Cragin's Top Attractions

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Cragin Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 507 verified family-friendly vacation rentals in Cragin. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Cragin vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $110 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Cragin 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 Cragin 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 Cragin often include amenities such as Child Friendly, Fireplace/Heating, and Guest Services. 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.