Chicago Private Home Rentals

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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Featured Private Holiday Homes in Chicago

Spacious Retreat Near Convention Centers 4 Bedroom Home by RedAwning
Living area

Spacious Retreat Near Convention Centers 4 Bedroom Home by RedAwning

3.5 star property
10.0 out of 10, Exceptional, (1)
"Everything was great!! "
Spacious Retreat Near Convention Centers 4 Bedroom Home by RedAwning
Modern Luxury Amenities Near Woodfield Mall 2 Bedroom Home by RedAwning
Exterior

Modern Luxury Amenities Near Woodfield Mall 2 Bedroom Home by RedAwning

3.5 star property
Modern Luxury Amenities Near Woodfield Mall 2 Bedroom Home by RedAwning
Charming Oak Park 4BD/3.5BA and 2 Private Parking by AllSet Turnover
Private kitchen

Charming Oak Park 4BD/3.5BA and 2 Private Parking by AllSet Turnover

3.0 star property
Charming Oak Park 4BD/3.5BA and 2 Private Parking by AllSet Turnover
Charming Contemporary Family Home 3 Bedroom Home by RedAwning
Private kitchen

Charming Contemporary Family Home 3 Bedroom Home by RedAwning

3.5 star property
Charming Contemporary Family Home 3 Bedroom Home by RedAwning
Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning
Exterior

Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning

3.0 star property
Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning
Lake view house
Interior detail

Lake view house

4.0 star property
Lake view house
The Elmhurst Experience
Private kitchen

The Elmhurst Experience

2.0 star property
The Elmhurst Experience
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chicago

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (695)
"Amazing and clean experience I highly recommend "
The price is S$237
includes taxes & fees
12 Mar - 13 Mar
Sentral Michigan Avenue
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (447)
"Amazing space - I'll be requesting the same one in the summer :) Spacious and clean! Absolutely loved the view of Willis Tower from our room. Excellent stay!"
The price is S$147
includes taxes & fees
1 Apr - 2 Apr
Sonder South Wabash
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (146)
"⭐️⭐️⭐️⭐️⭐️ Had a fantastic stay at Sonder Chicago West Loop during my business trip! The location was perfect for meetings, and I loved having the extra space. The studio felt more like an apartment—super clean, spacious, and well-appointed with stylish decor. The kitchen was fully stocked and well-maintained, making the stay even more comfortable. The reception area was great for getting work done before check-in, and the luggage room lockers were a huge plus. The app-based entry system was...
The price is S$197
includes taxes & fees
1 Apr - 2 Apr
Sonder The Burnham Apartments
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.