Chicago Rentals By Owner

There are a lot of options in Chicago. If you plan on staying in the Chicago area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Chicago:

• 52nd Floor MagMile Penthouse Views Fireplace Pool
• Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
• 55th Floor Penthouse with Award-Winning Views
• 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
• Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
• 53 Floor MagMile Penthouse Views, Balcony, Pool
• 51st Floor MagMile Penthouse Views Balcony Pool
• 2-Story Penthouse Views, Fireplace, Pool, Gym
• Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
• Great Location-Beautiful Friendly Andersonville Neighborhood

There are many large, family-friendly vacation homes available in Chicago; however, here are the most popular family rentals listed on our site:

• Riverfront Cottage
• Cottingham Cottage
• Meyers Bay Sunset Lakefront Cottage in Fox Lake with Boat Pier
• Little Fox Cottage - A Cozy Riverview Getaway Near Chicago
• Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
• Homan Square
• 3-bedroom hillside property in woods with fireplace and lake view
• Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood

Yes, there are 4 self-catering vacation homes in Chicago that have hot tubs, swimming pools, & other amenities.

There are more than 4 luxury villas and vacation homes in or near Chicago. Filter by price to compare find the most expensive places to stay on Piratecovecottages.

Yes, there are 4 pet friendly vacation homes and places to stays that are available in or near Chicago that you may consider.