170 pet-friendly stays
Most incredibly located, sun-filled home with designer kitchen, marble baths, and open-concept living areas—perfect for weekend friend getaways and weekday family or work trips.Walkable to so much of what Chicago has to…
$469 / night View listingWelcome to Your Chicago GetawayThis spacious home comfortably accommodates up to 12 guests, ideal for romantic getaways, family reunions, or gatherings with friends. With private keyless entry and a car garage, check-in…
$469 / night View listingWelcome to our contemporary, luxurious living experience! This 4BR Chicago home with a gym is ideal for an unforgettable family vacation, a trip with friends, or a group of digital nomads. Our home is conveniently…
$470 / night View listingSummary: 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. Stunning 1,400+ square foot penthouse…
$488 / 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…
$489 / night View listingImagine a stone castle, medieval style; except this one has an 85\ HDTV, Wifi, 16 long granite bar with full kitchen and appliances. The warm glow of recessed lighting and polished concrete floors create an atmosphere…
$500 / night View listingFeel at Home, Unwind, and Enjoy the amenities you deserve at our 3bed 2-Story Penthouse.Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because:✅Central location near…
$512 / night View listingMy charming 3-bedroom apartment has everything you need for your Chicago trip. The unit comes with washer/dryer in building, laptop-friendly workspace, and a fully loaded kitchen for all your culinary needs. The condo…
$513 / night View listingWrigleyville condo is located 1/2 block from Wrigley Field and Clark Street. Also close to Southport corridor and Brown Line. Easy access to Red Line which will take you downtown, Millenium Park, Grant Part, Maggie…
$513 / night View listingNEW HOME/NEWLY FURNISHED! This 6 bed single family home is ready to host! My space accomodates 12 guests with 6 beds and 4 full baths. You will find a fully stocked kitchen, comfortable beds, a furnished back deck,…
$516 / night View listingNEW 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 listing
