Holiday rentals in Chicago
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Top-rated holiday rentals in Chicago
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago holiday rentals
Other great holiday rentals in Chicago
Guest favourite
Guest suite in Chicago
4.98 out of 5 average rating, 110 reviewsGorgeous Studio 15 Minutes From Ohare!
24–31 Mar
£100 per night
Guest favourite
Flat in Humboldt Park
4.98 out of 5 average rating, 105 reviewsHumboldt Park Loft
4–11 Sept
£133 per night
Guest favourite
Home in Berwyn
4.92 out of 5 average rating, 237 reviewsPrivate apartment with retro vibe
4–11 Sept
£95 per night
Guest favourite
Flat in Chicago
4.91 out of 5 average rating, 370 reviewsThe Grotto of Logan Square
9–14 Sept
£136 per night
Guest favourite
Guest suite in Chicago
4.97 out of 5 average rating, 224 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
3–10 Oct
£121 per night
Guest favourite
Flat in Oak Park
4.85 out of 5 average rating, 527 reviewsLong stays welcome@warm&cute vintage 2BR
10–17 Sept
£105 per night
Guest favourite
Flat in Chicago
4.96 out of 5 average rating, 255 reviewsLogan Square 2nd Floor Chicago Victorian
30 Mar – 6 Apr
£131 per night
Guest favourite
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
28 Mar – 4 Apr
£118 per night
Quick stats about holiday rentals in Chicago
Total rentals
10K properties
Rentals with dedicated workspaces
6.6K properties have a dedicated workspace
Rentals with a pool
1.1K properties have a pool
Pet-friendly rentals
3.3K properties allow pets
Family-friendly rentals
4.8K properties are a good fit for families
Total number of reviews
466K reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Rentals with breakfast Chicago
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