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

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1394 Best Vacation Rentals in Cragin (Starting from $175)

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
Peaceful Oasis - Captivating Six-Bedroom Escape
Peaceful Oasis - Captivating Six-Bedroom Escape
Apartment
Chicago, IL, 60639, United States
0.2k from Cragin center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

6 Bedrooms14 Guests
New to Booking
$913
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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1BR 1BA Windy City Hideout
1BR 1BA Windy City Hideout
Apartment
Chicago, IL, 60639, United States
0.3k from Cragin center

Crib, Dryer, Heater, Internet, Kitchen, Laundry, No Smoking, TV, Washer

1 Bedroom2 Guests
New to Booking
$200
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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2BR Cozy & Functional Unit
2BR Cozy & Functional Unit
Apartment
Chicago, IL, 60639, United States
0.3k from Cragin center

Crib, Dryer, Heater, Internet, Kitchen, Laundry, No Smoking, TV, Washer

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$197
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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 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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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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1BR Retreat: Roomy & Well-Appointed
1BR Retreat: Roomy & Well-Appointed
Apartment
Chicago, IL, 60641, United States
0.6k from Cragin center

Crib, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking, TV, Washer

2 Bedrooms2 Guests
New to Booking
$175
Average price / night
Check Availability
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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Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Apartment
Chicago, IL, 60639, United States
0.6k from Cragin center

AC, Barbecue, Crib, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms7 Guests
New to Booking
$386
Average price / night
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Hermosa House apartment - Peaceful Quiet 3BR, Free Street Parking, Solar Powered, by Logan Square
Hermosa House apartment - Peaceful Quiet 3BR, Free Street Parking, Solar Powered, by Logan Square
Apartment
Chicago, IL, USA
2.2k from Cragin center

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

3 Bedrooms3 Guests
8.9

Fabulous

11 reviews

$360
Average price / night
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2BR w/ Workspace - Coffee Bar - Near Transit
2BR w/ Workspace - Coffee Bar - Near Transit
Apartment
Chicago, IL, 60639, United States
0.6k from Cragin center

AC, Barbecue, Crib, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms5 Guests
New to Booking
$382
Average price / night
Check Availability
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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2BR Traveler's Favorite • Modern and Clean
2BR Traveler's Favorite • Modern and Clean
Apartment
Chicago, IL, 60639, United States
0.6k from Cragin center

AC, Barbecue, Crib, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms5 Guests
New to Booking
$380
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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Two Bedroom - Tranquil Retreat
Two Bedroom - Tranquil Retreat
Apartment
Chicago, IL, 60639, United States
0.6k from Cragin center

No Smoking

2 Bedrooms4 Guests
New to Booking
$331
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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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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NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!
NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!
House
Chicago, IL, 60639, United States
1.0k from Cragin center

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

5 Bedrooms12 Guests
10.0

Exceptional

9 reviews

$829
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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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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2 Mi to Logan Square: Pet-Friendly Urban Oasis!
2 Mi to Logan Square: Pet-Friendly Urban Oasis!
Apartment
Chicago, IL, 60639, United States
1.2k from Cragin center

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

2 Bedrooms4 Guests
10.0

Exceptional

7 reviews

$274
Average price / night
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4BR Bright City Retreat-Sleeps 12-Garage Parking
4BR Bright City Retreat-Sleeps 12-Garage Parking
House
Chicago, IL, 60639, United States
1.4k from Cragin center

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

5 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$871
Average price / night
Check Availability
Game Room • Fire-pit • Playground • Gym • Billiard
Game Room • Fire-pit • Playground • Gym • Billiard
House
Chicago, IL, 60639, United States
1.5k from Cragin center

AC, Barbecue, Crib, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking

4 Bedrooms9 Guests
New to Booking
$643
Average price / night
Check Availability
Vantage appartement 9' ceiling, just renovated
Vantage appartement 9' ceiling, just renovated
Apartment
Chicago, IL, 60639, United States
1.5k from Cragin center

Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking, TV

2 Bedrooms4 Guests
New to Booking
$201
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 Vacation Rentals in Cragin.

Stay Near Cragin's Top Attractions

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Cragin Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1394 verified vacation rentals in Cragin. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Cragin vary depending on the season, property size, and location. Rates typically start from around $175 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Cragin include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Cragin welcome pets. Currently, 42 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Cragin often include amenities such as Fireplace/Heating, Kitchen, and Laundry. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.