Holiday houses 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
Superhost
Apartment in Chicago
4.89 out of 5 average rating, 105 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
17 – 24 Feb
$1,660 AUD total
Guest favourite
Guesthouse in Chicago
4.88 out of 5 average rating, 106 reviewsThe Roscoe Village Guesthouse
26 Jan – 2 Feb
$1,591 AUD total
Guest favourite
Cabin in Griffith
4.91 out of 5 average rating, 152 reviewsBeautiful Rustic Cabin for Two!
8 – 15 Jan
$1,048 AUD total
Guest favourite
Guesthouse in Chicago
4.99 out of 5 average rating, 782 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
25 Oct – 1 Nov
$1,965 AUD total
Guest favourite
Apartment in Chicago
4.95 out of 5 average rating, 103 reviewsComfortable, modern apartment 20 Min from Downtown
4 – 11 Nov
$1,685 AUD total
Guest favourite
Guest suite in Chicago
4.97 out of 5 average rating, 224 reviewsPrivate Suite w/ offstreet pkg, at Logan Sq Blu Ln
31 Aug – 7 Sept
$1,654 AUD total
Guest favourite
Guesthouse in Chicago
4.95 out of 5 average rating, 366 reviewsCozy Coach House
19 – 26 Aug
$1,568 AUD total
Guest favourite
Guest suite in Chicago
4.93 out of 5 average rating, 192 reviewsCozy Urban Garden Apartment
22 – 29 Apr
$1,114 AUD total
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 a fireplace Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
- Villa rentals Chicago
- Fitness-friendly rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with an accessible height bed Chicago
- Apartment rentals Chicago
- Pet-friendly rentals Chicago
- Townhouse rentals Chicago
- Rentals with a patio Chicago
- Rentals with a fire pit Chicago
- Rentals with outdoor seating Chicago
- Lakehouse rentals Chicago
- Boutique hotel rentals Chicago
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- Rentals with an EV charger Chicago
- Hotel rentals Chicago
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- Rentals with a home theatre Chicago
- Rentals with lake access Chicago
- Mansion rentals Chicago
- Bed and breakfasts Chicago
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- Rentals with breakfast Chicago
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- Loft rentals Chicago
- Rentals with pools Chicago
- Rentals with a balcony Chicago
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- Monthly Rentals Chicago
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- Smoking-friendly rentals Chicago
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