170 pet-friendly stays
Summary: NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2nd rooftop remains open and available for guests to use. 2 stylish corner apartments in a perfect…
$717 / night View listingFantastic location in the heart of Wrigleyville! Just a 5-minute walk to Wrigley Field and a block from The Metro concert venue. Steps away from iconic restaurants, cafes, and entertainment. Minutes from the interstate…
$722 / night View listingKick back and relax in this calm, stylish space that features 4 bedrooms, a large basement with bar, fully stocked kitchen and dining space for get-togethers. Enjoy beautiful Chicago summers in one of the various…
$750 / night View listingWelcome to Luxe Chicago, your exclusive Fulton Market penthouse retreat. This 3-bedroom, 2-bath designer loft offers 2,400 square feet of open-concept living space with soaring 14-foot ceilings, expansive windows, and…
$775 / night View listingHave fun with the whole family at this stylish place.Your family will be close to everything when you stay at this centrally-located place.The spaceIn need of a place to stay , relax, unwind and have a great time with…
$788 / night View listingWalk to everything Chicago has to offer- Downtown and Mag Mile; North ave beach, zoo and Lincoln park, restaurants, bars, boutiques; bring family or friends to this large property on a quiet neighborhood street in…
$879 / night View listingSummary:Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after locations in the city!Located on one of Chicago’s famous streets, you’ll be a 5-minute walk from the…
$935 / night View listingRENT WITH CONFIDENCE FROM A PREMIER HOST WITH OVER 800 POSITIVE REVIEWS!One-of-a-kind opportunity to rent a historic Gilded Age Chicago Gold Coast mansion. All modern amenities meet Romanesque Revival style at this huge…
$1,049 / night View listingTime Out magazine calls us one of the Best Chicago Rentals! HUGE mansion with six bedrooms, two living rooms, and four parking spots! Sleeps 21–everyone fits! Three blocks from Red & Purple line train stop. Twenty…
$1,112 / night View listingLoft606 Chicago is the perfect spot for private gatherings, weddings, corporate meetings, pop-up events, art exhibitions, reunions, dinner parties, birthday parties, classes, photo shoots, holidays, Bar Mitzvahs, and so…
$1,385 / night View listingOur custom-built house is perfect for a group of guests wanting to experience Chicago to its fullest. The home is a brand new modern masterpiece located in the heart of Old Town and central to all the attractions the…
$1,504 / night View listingChicago’s Gold Coast Luxury Single Family Home. The location is so perfect it cannot be beat! IG: ChicagoLuxuryVRBO. We offer additional services please inquire for any special needs. Chauffeur, private chef, private…
$2,700 / night View listing
