Holiday Homes in Chicago, IL

Search among 129 available holiday homes in Chicago from 50+ providers.

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21-40 out of 129
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Spacious Bucktown SanctuaryVilla
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5.7 km from City Centre
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Huge Lakeview Retreat Sleeping 20 With Parking!Villa
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7.1 km from City Centre1.1 km from Wrigley Field
FromC$ 681 /nightSelect
Spacious Ukrainian Village RetreatVilla
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4.1 km from City Centre1.7 km from United Center
FromC$ 423 /nightSelect
Spacious Lakeview Hideway With Parking!Villa
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7.1 km from City Centre1.1 km from Wrigley Field
FromC$ 364 /nightSelect
Luxe Spacious Sfh In Bucktown With Secure ParkingVilla
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5.8 km from City Centre
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Modern Lincoln Park Hideaway 1 Bd And 1BathVilla
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6.6 km from City Centre1.9 km from Wrigley Field
FromC$ 421 /nightSelect
A Home Away From Home!Villa
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16.6 km from City Centre1000 m from Bronzeville Children's Museum
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Cozy Home In Washington HeightsVilla
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17.8 km from City Centre2.0 km from Abbott Park
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Stylish Chicago Retreat, Walk To Loyola UniversityVilla
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13.4 km from City Centre
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2 Mtm Fully Furnished Rental In Old Town 2F&2RVilla
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3.9 km from City Centre1.9 km from Michigan Avenue
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2 Suites 2 Floors In Downtown ChicagoVilla
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3.0 km from City Centre
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Stunning 2 Floor Penthouse DowntownVilla
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3.0 km from City Centre
FromC$ 888 /nightSelect
3 Flat Building Downtown - With Private PatiosVilla
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3.0 km from City Centre
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870 1&2 - 2 Separate Suites In Same BuildingVilla
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2.5 km from City Centre1.1 km from Michigan Avenue
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5 Bedroom House In Best Location Parking Fireplace Back Yard Home OfficeVilla
24 adults
5 bedrooms
10 beds
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3.6 km from City Centre1.8 km from Michigan Avenue
The Art Institute of Chicago is within 10 minutes' drive of the Old Town-Gold Coast Huge 5 Bedroom Home/ Free Parking/ Breakfast/ Pets Ok/ Back Yard/ Walk Everywhere.
FromC$ 839 /nightSelect
Beautifully Renovated House 10 Mins From DowntownVilla
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6.8 km from City Centre
FromC$ 1 016 /nightSelect
Luxe 6Br House Trendy Logan Square Garage AccessVilla
16 adults
6 bedrooms
6 beds
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8.3 km from City Centre
Composed of 6 bedrooms and 4 bathrooms, this holiday home is set only 1.3 km from California & Milwaukee.
FromC$ 679 /nightSelect
Gold Coast Villa With Free Parking Garage Sleeps 10Villa
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3.0 km from City Centre1.0 km from Michigan Avenue
Tribune Tower and Skydeck Chicago are located 1.2 km and 2.4 km from the Gold Coast Villa With Free Parking Garage Sleeps 10 respectively.
FromC$ 3 893 /nightSelect
Lincoln Park 2 Bedroom Condo Wmid Century FlairVilla
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5.5 km from City Centre400 m from Treasure Island Market Square Shopping Center
The Lincoln Park 2 Bedroom Condo Wmid Century Flair is located 20 km from Midway International airport and at 350 metres of Cortland & Kingsbury EB bus stop.
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Beautiful 5Br Home For 14 Guests With Free ParkingVilla
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3.0 km from City Centre1.9 km from Michigan Avenue
Set within 2.6 km of Willis Tower, the rooms in the Beautiful 5Br Home For 14 Guests With Free Parking Chicago have views of garden.
FromC$ 1 691 /nightSelect
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Guest reviews of hotels in Chicago