Chicago Family Rentals & Large Homes
Find Family-Friendly Vacation Rentals Near Chicago
When do you want to travel?
We search multiple sites to find you the best prices.
3.0
(193 Reviews)
- Parking
- Child Friendly
- Internet
10.0
(242 Reviews)
- Air Conditioner
- Parking
- TV
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House
10.0
(21 Reviews)
- Air Conditioner
- Parking
- TV
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Apartment
9.7
(18 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
10.0
(167 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
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Apartment
New
- Air Conditioner
- Pet Friendly
- Child Friendly
10.0
(119 Reviews)
- Air Conditioner
- Parking
- TV
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Apartment
9.0
(1 Review)
- Air Conditioner
- Parking
- Child Friendly
9.8
(227 Reviews)
- Air Conditioner
- Parking
- TV
9.6
(27 Reviews)
- Air Conditioner
- Parking
- TV
10.0
(38 Reviews)
- Air Conditioner
- Parking
- TV
10.0
(38 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
10.0
(408 Reviews)
- Air Conditioner
- Parking
- Pool
10.0
(227 Reviews)
- Air Conditioner
- Parking
- Pool
9.8
(33 Reviews)
- Air Conditioner
- TV
- Balcony/Terrace
10.0
(112 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
9.8
(53 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
9.6
(187 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
9.6
(19 Reviews)
- Balcony/Terrace
- Security/Safety
- Fireplace/Heating
10.0
(112 Reviews)
- Air Conditioner
- Parking
- TV
8.4
(19 Reviews)
- Air Conditioner
- Parking
- TV
10.0
(96 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
9.0
(14 Reviews)
- Balcony/Terrace
- Security/Safety
- Child Friendly
9.6
(56 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
Frequently Asked Questions About Chicago Family Rentals
What are the top rated Family Rentals in Chicago?
There are a lot of options in Chicago. If you plan on staying in the Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the top Family Rentals in Chicago:
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 55th Floor Penthouse with Award-Winning Views
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- 53 Floor MagMile Penthouse Views, Balcony, Pool
- 2-Story Penthouse Views, Fireplace, Pool, Gym
- NEW LUXURY PENTHOUSE CONDO
- Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
- Magic Factory Loft 2West
- Great Location-Beautiful Friendly Andersonville Neighborhood
- NEW LUXURY CONDO WITH PATIO DECK
How much does it cost to rent a family vacation rental in or near Chicago?
The average price per night for a family holiday rental in Chicago is $400. Check the list of kid-friendly accommodations in Chicago.
How many 2-bedroom apartment rentals are available to book in Chicago?
There are 6899 2-bedroom rental properties that are available in Chicago. You can book for your next trip with Chicagosbestvacationrentals.
Do any family-friendly vacation rentals in Chicago have a pool?
Yes, here are some top-rated family vacation rentals in Chicago that have a private swimming pool:
- Homan Square
- Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
- Wrigleyville Inn
- Luxurious Stay at Modern Apartment with Self Check-in Mins Frm Downtown
Check all holiday rentals with a pool in Chicago on Chicagosbestvacationrentals.
Can I find private owner rentals in Chicago?
Yes, We have 6899 direct by owner rentals in Chicago.