Pet-friendly vacation rentals in Downtown Chicago

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Downtown Chicago

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

Superhost
Apartment in Chicago
River North's Rock N Roll
Much Safer during Covid, No Common Areas. Avoid high-rises / hotels. Monthly Bookings Available, message to inquire about pricing. Decorated with rock n' roll memorabilia and located above a trendy restaurant, this cozy apartment also features high ceilings and a carved canopy bed. Minutes to Mag Mile and the Loop! Free parking available when requested at booking. Great space...Great Location. Only blocks from Michigan Avenue shopping district and blocks from downtown loop. CTA Brown line station across the street. River North Art Galleries one street south. Great Dining, Millennium Park and all that Chicago has to offer only minutes away. Divvy bike station around the corner. Jump on the Brown Line across the street, be at Wrigley Field in 15 minutes. Parking Included based upon availability when requested at time of booking. A beautiful apartment with fully equipped kitchen, 65" TV with cable and HBO. Little to none... The apartment is located in River North, one of Chicago's trendiest neighborhoods. It is blocks away from Michigan Avenue, the Loop, and River North Art Galleries. This neighborhood is also a short train ride from Millennium Park and Wrigley Field. Jump on the CTA Brown Line across the street...tour the Loop... be at Millennium Park, Grant Park or Nave Pier in minutes... 15 minutes to Wrigley Field. Even Divvy bike sharing location 150 feet away. Well trained dogs welcome!
Nov 1 – 8
$319 per night
4.89 out of 5 average rating, 254 reviews
Superhost
Apartment in Chicago
Spectacular Corner 2BR Penthouse in the Loop | Roo
This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, 13 foot tall ceilings and oversized windows, this spacious penthouse is a true escape in the sky in the heart of downtown Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed, ideal for families, business travelers, or couples traveling together. The building has a pool and an amazing outdoor rooftop terrace with 360 degree vi
Oct 19 – 26
$504 per night
4.86 out of 5 average rating, 185 reviews
Guest favorite
Guest suite in Chicago
Stylish Studio in Historic Logan Square
Brand new, unique garden studio (4 steps down), located in the heart of the highly desirable Logan Square neighborhood. This luxurious space with heated floors & a spa inspired bathroom is situated on the Historic Logan Boulevard, 2 blocks from the CTA Blue Line which runs between downtown & O'Hare airport. The suite has a private entrance & access to a fabulous shared backyard space. The owner's treehouse deck can be reserved by request. Convenience & excitement are easily accessible!​
Apr 1 – 8
$125 per night
4.97 out of 5 average rating, 225 reviews

Popular amenities for Downtown Chicago pet-friendly home rentals

Pet-friendly house rentals

Guest favorite
Home in Chicago
Chicago Riverhouse private chill patio comfy beds
Oct 24 – 31
$261 per night
4.96 out of 5 average rating, 122 reviews
Guest favorite
Home in Chicago
Private 3rd Floor Apartment
Nov 8 – 15
$109 per night
4.89 out of 5 average rating, 330 reviews
Guest favorite
Home in Forest Park
Charming dog friendly 2-Bath Bungalow Near Chicago
May 23 – 30
$121 per night
4.9 out of 5 average rating, 216 reviews
Guest favorite
Home in Chicago
The Avondale Guesthouse
Oct 22 – 29
$81 per night
4.86 out of 5 average rating, 212 reviews
Guest favorite
Home in Chicago
Historic Old Town, Fabulous 4 Bedroom Home
Sep 27 – Oct 4
$370 per night
4.81 out of 5 average rating, 129 reviews
Guest favorite
Home in Berwyn
Private apartment with retro vibe
Aug 10 – 17
$92 per night
4.92 out of 5 average rating, 225 reviews
Guest favorite
Home in Chicago
Huge Home * Yard * Parking * Best Location
Mar 3 – 10
$296 per night
4.85 out of 5 average rating, 113 reviews
Guest favorite
Home in Chicago
Amazing Penthouse Skyline Views!
Apr 19 – 26
$413 per night
4.93 out of 5 average rating, 322 reviews
Superhost
Home in Chicago
Bucktown Home W/ Free Garage Parking for 2 Cars!
Aug 2 – 9
$716 per night
4.83 out of 5 average rating, 116 reviews
Superhost
Home in Chicago
ALOHA | Tropical Penthouse Designer Home
Sep 5 – 12
$825 per night
4.9 out of 5 average rating, 172 reviews
Guest favorite
Home in Chicago
Wrigley Retreat - Full Home w/ Chicago Charm
Jan 26 – Feb 2
$690 per night
4.94 out of 5 average rating, 105 reviews
Guest favorite
Home in Chicago
Victorian House in Heart of Rogers Park
Aug 7 – 14
$458 per night
4.98 out of 5 average rating, 57 reviews

Pet-friendly home rentals with a pool

Guest favorite
Home in Highland Park
2-Acre Highland Park Retreat with Heated Pool ~ 5*
Apr 9 – 16
$848 per night
4.9 out of 5 average rating, 123 reviews
Superhost
Apartment in Itasca
King Bed at Chicago Northwest + PET Friendly
Aug 18 – 25
$999 per night
4.77 out of 5 average rating, 169 reviews
Guest favorite
Apartment in Chicago
Dtown Penthouse 2bd/2.5ba (+Parking, Pool, Gym)
Apr 26 – May 3
$444 per night
4.94 out of 5 average rating, 33 reviews
Superhost
Apartment in Chicago
Luxe Suite + Spa House Retreat! Pets Welcome
Dec 21 – 28
$138 per night
4.9 out of 5 average rating, 20 reviews
Superhost
Apartment in Chicago
Skyline Oasis: City & Lake Views
Jun 19 – 26
$369 per night
5.0 out of 5 average rating, 10 reviews
Guest favorite
Campsite in Midlothian
Waverly Woods Outpost: Private Glampsite w Theater
Sep 25 – Oct 2
$162 per night
4.99 out of 5 average rating, 76 reviews
Superhost
Apartment in Schaumburg
PrimeLocation:pool, fitness, dog park A+ amenities
May 22 – 29
$152 per night
5.0 out of 5 average rating, 3 reviews
Superhost
Apartment in Chicago
Luxury Designer Penthouse South |Pool| Gold Coast
Oct 3 – 10
$783 per night
New place to stay
Apartment in Chicago
Kasa | Nearby Millennium Park | River North
Nov 9 – 16
$130 per night
4.84 out of 5 average rating, 175 reviews
Apartment in Chicago
Guest king Room at Aloft Chicago Mag Mile
Apr 2 – 9
$135 per night
New place to stay
Apartment in Chicago
Let’s make a toast in the “Gold Coast ”
Feb 8 – 15
$128 per night
4.73 out of 5 average rating, 37 reviews
Apartment in Chicago
Sentral 1BR Premium Apt in South Loop Chicago
Aug 17 – 24
$483 per night
4.57 out of 5 average rating, 81 reviews

Private, pet-friendly home rentals

Superhost
Apartment in Chicago
1BR Perfect Home in the City, Close to Everything
Apr 29 – May 6
$123 per night
4.88 out of 5 average rating, 129 reviews
Guest favorite
Townhouse in Chicago
⭐️Cozy Garden Unit by Downtown & Blue Line Stop⭐️
Apr 25 – May 2
$97 per night
4.87 out of 5 average rating, 132 reviews
Guest favorite
Condo in Chicago
Lincoln Square Gem!
May 6 – 13
$145 per night
4.98 out of 5 average rating, 325 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 Chicago
Bright and Cozy 1BR Apartment in Logan Square!
Mar 18 – 25
$90 per night
4.87 out of 5 average rating, 129 reviews
Guest favorite
Apartment in Logan Square
Best in Chicago, private, amazing garden space
Apr 6 – 13
$214 per night
4.95 out of 5 average rating, 644 reviews
Guest favorite
Apartment in Chicago
Bright family-friendly Lincoln Square 2-bed 1-bath
Nov 12 – 19
$115 per night
4.96 out of 5 average rating, 312 reviews
Superhost
Apartment in Chicago
Relaxed Bucktown/Wicker Park 1B Apt
Apr 9 – 16
$72 per night
4.84 out of 5 average rating, 472 reviews
Guest favorite
Apartment in Chicago
Unwind in the Garden of an elegant, Modern Home
Jan 1 – 8
$135 per night
4.87 out of 5 average rating, 295 reviews
Guest favorite
Apartment in Chicago
Sunny Logan Square Artists' home
Sep 2 – 9
$105 per night
4.89 out of 5 average rating, 330 reviews
Guest favorite
Apartment in Chicago
Ravenswood Manor, Sleeps 4! Close to El and Parks
Jan 14 – 21
$97 per night
4.89 out of 5 average rating, 171 reviews
Guest favorite
Guest suite in Chicago
Comfortable & Cozy in Bridgeport
Apr 7 – 14
$85 per night
4.94 out of 5 average rating, 117 reviews

Destinations to explore