99 pet-friendly stays
NEW HOME/NEWLY FURNISHED! This 8 bed home is ready to host! My space accomodates 18 guests with 10 beds and 4 full baths and a fully stocked kitchen. We are minutes from the best restaurants and bars. Both MDW and ORD…
$518 / night View listingUnique opportunity to rent an original Victorian home in historic Old Town. Only listing of its kind!Walk to almost everything Chicago has to offer- Downtown, Magnificent mile, restaurants, bars, boutiques; Lincoln Park…
$524 / night View listingSummary:Gather your favorite people at The Winfrey, our exclusive offering of two luxury apartments, perfect for your groups special Chicago gathering. Our commitment to a pristine stay is clear, with a perfect 100%…
$526 / night View listingLight and airy custom built home across from Humboldt Park with expansive views of the Humboldt Park pond/lake. Spacious yet cozy, perfect for a family getaway or a large group of friends.The spaceHuge open concept…
$529 / night View listingSummary:NEW PENTHOUSE LOFT IN FULTON MARKET!Enjoy your own private luxury loft in Chicagos bustling Fulton Market-the citys center of main nightlife, restaurants and cultural scene. This 3,500 square foot penthouse…
$543 / night View listingThe Greenleaf House, built in 1915, is our 3600ft² home with 6 bedrooms, 2.5 baths, & an open floor plan—perfect for gatherings of any kind. Were in the heart of the Rogers Park neighborhood, walking distance from many…
$552 / night View listingSummary:NEWLY RENOVATED TOWNHOUSE IN THE HEART OF LINCOLN PARK!This private luxury townhouse (duplex) is perfectly located-surrounded by nightlife, restaurants, cultural attractions, and is only two blocks from DePaul…
$578 / night View listingIn a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and vibrant nightlife in this hub for arts and entertainment. The best shopping in Chicago is minutes…
$586 / night View listingSummary:BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicagos newest and most luxurious building in bustling River North-the citys center of main nightlife and restaurants. This ultra high-end…
$598 / night View listing\Welcome to your exclusive 2-story haven flooded with natural light! Dual TV areas with brand new 70\ and 55\ TVs create a modern retreat in vibrant LakeView/Lincoln Park, surrounded by fantastic dining and nightlife. A…
$618 / night View listing🛏 Sleeping Arrangements, Plenty of room for everyone to have their own space!Bedroom 1: King bedBedroom 2: Queen bedBedroom 3: Queen bedBedroom 4: Queen bedAir mattresses with extra pillows, blankets, and linens are…
$650 / night View listingSummary:Your familys perfect Chicago retreat awaits at The Soul, a spacious 4BR penthouse featuring a kids room, two balconies, and a safe, walkable neighborhood. Its a family-approved favorite, with over 9 out of 10…
$675 / night View listing
