Chicago Winter Rentals & Holiday Homes

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 Winter Rentals in Chicago:

• NEW LUXURY PENTHOUSE CONDO
• Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
• Great Location-Beautiful Friendly Andersonville Neighborhood
• NEW LUXURY CONDO WITH PATIO DECK
• 1F Chicago's Little italy Graystone nearDowntown
• Amazing Lincoln Park Rowhouse - Perfect for Groups, Reunions and Cubs Games!
• Dramatic Wrigley Loft +PRIVATE Rooftop, Center of Wrigley, Ranked GUEST FAVORITE
• Spacious 3BR Duplex for Groups-Near Airport & Downtown-Cozy & Quiet
• Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
• Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.

The average cost for winter rentals in Chicago is $566 per night. Chicagosbestvacationrentals has a wide list of great winter places to stay near Chicago that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Yes, here are the top cottage/chalet rentals in Chicago that allow you to bring your pet or dog:

• Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
• Designer Home in Ukrainian Village - Chicago
• The Sono Chicago
• Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood

See all pet-friendly vacation rentals in Chicago on Chicagosbestvacationrentals

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Chicago to find what works for you.

As of 2026, the data from Chicagosbestvacationrentals shows that there are over 1454 private swimming pools or indoor pools accommodations near Chicago along with other great amenities.