House vacation rentals in Downtown Chicago
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Top-rated house rentals in Downtown Chicago
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Downtown Chicago house rentals
House rentals with a pool
Home in Glen Ellyn
4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
Home in Chicago
4.86 out of 5 average rating, 29 reviews2Bed+2Bath PentHouse in South Loop
Home in Bloomingdale
4.94 out of 5 average rating, 34 reviewsGiant Swimming Pool with Whole House!
Home in Riverwoods
Riverwoods Nature Retreat
Home in Bensenville
5 out of 5 average rating, 14 reviewsNew! Arcade+Sauna+Slots+Karaoke+more by O’Hare
Home in Schaumburg
4.82 out of 5 average rating, 11 reviewsSchaumburg Oasis with a Pool and Hidden Garden
Home in Chicago
New place to stayCity Close, Country Calm
Home in Itasca
New place to stayOceanFront Resort Studio at Garza Blanca Cancun MX
Weekly house rentals
Home in Chicago
4.93 out of 5 average rating, 350 reviewsAmazing Penthouse Skyline Views!
Home in Chicago
4.93 out of 5 average rating, 135 reviewsHouse 5BED/3BATH/1PARKING close to Downtown & Lake
Home in Chicago
4.95 out of 5 average rating, 108 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Home in Chicago
4.94 out of 5 average rating, 252 reviewsDuplex Home RoscoeVillage/Wrigley Free St Parking
Home in Glen Ellyn
4.92 out of 5 average rating, 127 reviewsHome in Glen Ellyn
Home in Glen Ellyn
4.96 out of 5 average rating, 100 reviews4bd house, Hot-tub, full-basement, pool table&yard
Home in Bolingbrook
4.92 out of 5 average rating, 116 reviewsThe Sunshine Spot
Home in Chicago
4.91 out of 5 average rating, 138 reviewsBest Bachelorette Pad El Motel Dos by @Bangtel
Private house rentals
Home in Chicago
4.94 out of 5 average rating, 122 reviewsWrigley Retreat - Full Home w/ Chicago Charm
Home in Lake Zurich
4.77 out of 5 average rating, 35 reviewsComfortable 4 bedroom home with indoor fireplace
Home in Chicago
4.89 out of 5 average rating, 46 reviews3BD/2BA Chicago Avondale/Logan Square House
Home in Schaumburg
4.92 out of 5 average rating, 50 reviewsEclectic Ranch Home with Large Private Fenced Yard
Home in Chicago
4.95 out of 5 average rating, 38 reviewsGorgeous and Luxurious 3 BR Home
Home in Chicago
4.84 out of 5 average rating, 102 reviewsPeaceful Family Home near Downtown, MDW, Free Park
Home in Westmont
4.93 out of 5 average rating, 30 reviewsWestmont,Il 4/3 on the Lake
Home in Elmhurst
4.74 out of 5 average rating, 109 reviewsKing Bed! Cozy ranch close to everything. 3 baths!
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- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes