
Holiday rentals with outdoor seating in Chicago
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Chicago
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Chicago Home (1st floor) by Midway near Downtown

3BD Home Mins from Airport | Free Wi-Fi + Parking

The Brookfield Breakaway w/ Game Room

Chicago River House -BBQ Oasis now open!

Unique porcelain-enamel paneled "Lustron" home

Entire first floor in Lincoln Square!

Big house in the BEST Location!

Boho Chic Coach House 30Min to downtown W/ Parking
Apartment rentals with outdoor seating

iKlektik House Chicago / Cardinal

Sunny 1 bedroom apartment 1 block from restaurants

Charming Unique 2 Bdrm Apartment in Victorian Home

Breathtaking & Chic Oasis Loc in Desirable Old Twn

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Logan Square Cozy 2BR Basement Apartment

Newly-renovated historic home in Logan Square

Funky & newly remodeled 1 bed in Hip Logan Square
Condo rentals with outdoor seating

Interior Designer’s 2bd 2bath w Private Backyard

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Logan Square Beauty with 2 Bedrooms W/parking

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

Spacious 4 Bedroom Condo

Updated Designer Duplex In Fulton Market W/parking

Spacious Evanston Unit - Walk to Northwestern U
Quick stats about holiday rentals with outdoor seating in Chicago
Total rentals
2.7K properties
Total number of reviews
196K reviews
Family-friendly rentals
1.8K properties are a good fit for families
Pet-friendly rentals
940 properties allow pets
Rentals with a pool
280 properties have a pool
Rentals with dedicated workspaces
2.2K properties have a dedicated workspace
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- South Haven Holiday rentals
- Saugatuck Holiday rentals
- Holland Holiday rentals
- South Side Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Rentals with a patio Chicago
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Garfield Park Conservatory
- Washington Park Zoo
- Wicker Park
- Illinois Beach State Park
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Chicago
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