Chicago Heights Holiday Houses

A cityscape with a marina, river, and high-rise buildings.

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Our top choices for Chicago Heights holiday homes

A living room with a brown sofa, a coffee table, and a patterned rug. There is a staircase leading to another room.

1. Spacious 3br home near Chicago, fenced yard for pets

Richton Park

Greg S.

includes taxes & fees

5 Oct - 6 Oct

A dining area with a black table set for four, surrounded by chairs. A vase with dried flowers and a candle holder are on the table.

2. 3-bedroom house in lovely Matteson with cool AC breeze

Matteson

Susan H.

A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

3. Romantic Escape - Adult Playhouse with Exotic Dungeon

South Holland

Anonymous traveller

includes taxes & fees

1 Oct - 2 Oct

A living room with a sofa, armchairs, a coffee table, and a rug.

4. Comfortable 3BR Home-Prime Video, WiFi, Parking

Schererville

Michael B.

A wooden deck with a railing, a staircase, and a window with a wreath.

5. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Robertsdale

Jusu K.

includes taxes & fees

4 Oct - 5 Oct

A living room with a brick fireplace, a television mounted above it, and a dining area with a table and chairs.

6. Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

Merrillville

Anonymous traveller

includes taxes & fees

1 Oct - 2 Oct

A spacious living room with a wooden staircase, a grey sofa, and a large window with blinds.

7. Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake

Cedar Lake

Steven M.

includes taxes & fees

1 Oct - 2 Oct

A modern kitchen with wooden cabinets, stainless steel appliances, and a white countertop island.

8. Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

Merrilville

"This is not a place to stay with small children; glad mine are grown for this stay. Also, the host really needs to have people they know stay there a bit to see what guests are really looking for. This property really felt like someone is just trying to make money and they don't really care about the people using the property. One of our beds was broken, there were limited furnishings and the tv in the living room was not user friendly at all. I would not recommend this property for any long...

Paula H.

includes taxes & fees

5 Oct - 6 Oct