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:

• 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
• 53 Floor MagMile Penthouse Views, Balcony, Pool
• 2-Story Penthouse Views, Fireplace, Pool, Gym
• Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
• Magic Factory Loft 2West
• Great Location-Beautiful Friendly Andersonville Neighborhood
• 1F Chicago's Little italy Graystone nearDowntown
• Amazing Lincoln Park Rowhouse - Perfect for Groups, Reunions and Cubs Games!

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

• Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
• Homan Square
• Wrigleyville Inn
• Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood

Yes, there are 9138 self-catering vacation homes in Chicago that have hot tubs, swimming pools, & other amenities.

There are more than 9138 luxury villas and vacation homes in or near Chicago. Filter by price to compare find the most expensive places to stay on Lakepost.

Yes, there are 9138 pet friendly vacation homes and places to stays that are available in or near Chicago that you may consider.