Family-friendly vacation rentals in Downtown Chicago

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Top-rated family-friendly rentals in Downtown Chicago

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Guest favorite
Apartment in Chicago
Amazing Location | Stunning Views | Free Parking
You will feel on top of the world as this luxury property truly has it all. With a 24 hour doorman, heated parking in the building, hot tub, workout and rec rooms, and views not to be beat, this property is in a beautiful and safe neighborhood in Chicago. Be at Mccormick place in under five minutes or dash off to all Chicago has to offer from our perfectly located condo in our Luxury South Loop flat. Close to public transport and an easy cab ride to the airports, we look forward to your stay!
Mar 5 – 12
$353 per night
4.86 out of 5 average rating, 148 reviews
Guest favorite
Apartment in Chicago
Fully Furnished Apartment Wicker Park Free Parking
Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available
Mar 31 – Apr 5
$109 per night
4.97 out of 5 average rating, 442 reviews
Guest favorite
Apartment in Chicago
Urban Chic Apartment by the Magnificent Mile
Ideally located just half a block from Michigan Avenue, this bright and open 3rd floor apartment boasts thoughtfully appointed rooms for your comfort so will have everything you need to enjoy your stay in style! PLEASE NOTE: 3rd floor walk up (NO ELEVATOR) There is a small neighborhood bar on the second floor of the building. They are respectful of our neighbors, however they do play music which can be heard in the living room but rarely, if ever, in the bedrooms.
Nov 14 – 21
$220 per night
4.94 out of 5 average rating, 210 reviews

Popular amenities for Downtown Chicago family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Home in Chicago
LOFT606: Gigantic Sunlit Former Factory Home
Apr 13 – 20
$964 per night
4.89 out of 5 average rating, 82 reviews
Guest favorite
Loft in Chicago
Artist Loft Duplex in a 1904 Former Factory
Jun 26 – Jul 3
$614 per night
4.81 out of 5 average rating, 278 reviews
Apartment in Chicago
Spacious 2bdm unit 15min to Dwtn
Apr 15 – 22
$131 per night
4.57 out of 5 average rating, 7 reviews
Apartment in Evanston
Lovely Furnished Evanston Apt.
Mar 6 – 13
$127 per night
4.27 out of 5 average rating, 16 reviews
Condo in Chicago
Cozy 2bd unit,10mins 4m dwntwn,IDEAL FOR LONG STAY
Jun 23 – 30
$126 per night
4.41 out of 5 average rating, 73 reviews

Family- and pet-friendly home rentals

Guest favorite
Apartment in Chicago
Sunny Logan Square Artists' home
Dec 26 – Jan 2
$94 per night
4.89 out of 5 average rating, 330 reviews
Superhost
Apartment in Chicago
River North's Rock N Roll
Dec 20 – 27
$320 per night
4.89 out of 5 average rating, 254 reviews
Guest favorite
Condo in Evanston
Spacious Evanston Unit - Walk to Northwestern U
Aug 17 – 24
$117 per night
4.76 out of 5 average rating, 553 reviews
Guest favorite
Apartment in Chicago
Roscoe Village One Bed Lux Apartment Near Wrigley
Nov 3 – 10
$90 per night
4.96 out of 5 average rating, 232 reviews
Guest favorite
Apartment in West Town
Unwind in the Garden of an elegant, Modern Home
Jan 7 – 14
$135 per night
4.87 out of 5 average rating, 295 reviews
Guest favorite
Townhouse in Hoffman Estates
a SIMPLE place
Oct 17 – 24
$85 per night
4.91 out of 5 average rating, 284 reviews
Guest favorite
Apartment in Logan Square
Best in Chicago, private, amazing garden space
Sep 8 – 15
$238 per night
4.95 out of 5 average rating, 645 reviews
Guest favorite
Guest suite in Chicago
Stylish Studio in Historic Logan Square
May 16 – 23
$141 per night
4.97 out of 5 average rating, 226 reviews
Superhost
Apartment in Wicker Park
Relaxed Bucktown/Wicker Park 1B Apt
Jul 21 – 28
$100 per night
4.84 out of 5 average rating, 472 reviews
Guest favorite
Home in Forest Park
Charming dog friendly 2-Bath Bungalow Near Chicago
Jun 12 – 19
$122 per night
4.9 out of 5 average rating, 216 reviews
Guest favorite
Home in Uptown
Private 3rd Floor Apartment
Dec 18 – 25
$128 per night
4.89 out of 5 average rating, 330 reviews
Guest favorite
Apartment in Chicago
✨Spacious Centrally Located West Loop Loft✨
Dec 16 – 23
$201 per night
4.93 out of 5 average rating, 201 reviews

Family-friendly home rentals with a pool

Superhost
Apartment in Chicago
Stylish Corner 2 Bedroom in the Heart of Chicago |
Nov 24 – Dec 1
$481 per night
4.77 out of 5 average rating, 181 reviews
Guest favorite
Apartment in The Loop
STUNNING VIEWS, 5★AMENITY BUILDING, FREE PARKING
Oct 27 – Nov 3
$552 per night
5.0 out of 5 average rating, 6 reviews
Guest favorite
Apartment in Forest Park
Comfy & Cute-Oak Park Area - Parking +Public Trans
Mar 13 – 20
$102 per night
4.91 out of 5 average rating, 11 reviews
Guest suite in Berwyn
Music Hot Spot’s Main Level
Oct 22 – 29
$105 per night
4.74 out of 5 average rating, 31 reviews
Guest favorite
Guest suite in Chicago
Sweet Home Chicago-9min downtown/pool/free parking
Nov 16 – 23
$176 per night
4.96 out of 5 average rating, 79 reviews
Superhost
Apartment in Chicago
Luxury Corner 2 Bedroom in the Loop | Roof Deck
Nov 18 – 25
$381 per night
4.77 out of 5 average rating, 197 reviews
Superhost
Apartment in Chicago
Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Dec 14 – 21
$877 per night
4.59 out of 5 average rating, 46 reviews
Place to stay in Berwyn
Beat-Town Flex Stays
Jan 16 – 23
$61 per night
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