Holiday rentals with outdoor seating in Chicago
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Chicago
Guests agree: these rentals 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 outdoor seating rentals in Chicago
House rentals with outdoor seating
Home in Chicago
4.98 out of 5 average rating, 205 reviewsWrigleyville Southport Studio
15–22 Dec
Home in Chicago
4.96 out of 5 average rating, 316 reviewsGet Cozy at a Powder-Blue Residence in the Heart of Pilsen
27 Mar – 3 Apr
Home in Chicago
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
16–23 Nov
Home in West Town
4.95 out of 5 average rating, 171 reviewsParadise on the Park
24 Sept – 1 Oct
Home in Forest Park
4.91 out of 5 average rating, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
20–27 Jun
Home in Roscoe Village
4.94 out of 5 average rating, 209 reviewsModern Home RoscoeVillage/Wrigley Free St Parking
27 Mar – 3 Apr
Home in Chicago
4.97 out of 5 average rating, 356 reviewsGreystone Haven in Logan Square
27 Jun – 4 Jul
Home in Joliet
4.84 out of 5 average rating, 158 reviewsCozy Private Cottage in the Cathedral District
11–18 Nov
Apartment rentals with outdoor seating
Flat in Chicago
4.89 out of 5 average rating, 176 reviewsHistoric Chicago neighborhood flat
13–20 Dec
Flat in Lake View
4.86 out of 5 average rating, 201 reviewsPrivate Queen Bedroom and En Suite Bath
2–9 Jul
Flat in Chicago
4.95 out of 5 average rating, 106 reviewsComfortable, modern apartment 20 Min from Downtown
15–22 Mar
Flat in West Town
4.98 out of 5 average rating, 218 reviewsUkrainian Village Garden Retreat
20–27 Nov
Flat in Chicago
4.98 out of 5 average rating, 128 reviewsModern Apt with style & comfort in Pilsen Chicago
9–16 Jul
Flat in Chicago
4.92 out of 5 average rating, 489 reviews2BR Bursting w/ Character in Hip Logan Square!
31 Mar – 7 Apr
Flat in Forest Park
5.0 out of 5 average rating, 219 reviewsLike a Treehouse!
4–11 Oct
Flat in Chicago
4.96 out of 5 average rating, 483 reviewsStunning Retro Apartment in Andersonville
2–9 Dec
Apartment rentals with outdoor seating
Apartment in Chicago
4.91 out of 5 average rating, 120 reviewsSpacious & Modern Family Friendly North Center Apt
26 Jan – 2 Feb
Apartment in Chicago
4.88 out of 5 average rating, 234 reviews2 King Bed Condo Easy Downtown Free Street Parking
7–14 Sept
Apartment in Chicago
4.9 out of 5 average rating, 135 reviewsEast Garfield Park 2 Bedroom
1–8 Mar
Apartment in Oak Park
4.79 out of 5 average rating, 308 reviewsPeaceful Oak Park Condo Next to Green Line Metro
12–19 Oct
Apartment in Chicago
4.9 out of 5 average rating, 190 reviewsA Stones Throw from U Chicago South Campus!
11–18 Jan
Apartment in Chicago
4.98 out of 5 average rating, 232 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
27 Oct – 3 Nov
Apartment in Chicago
4.91 out of 5 average rating, 246 reviewsOld Town Pied-à-Terre w/Pvt Terrace and Parking
19–26 Dec
Apartment in Chicago
4.98 out of 5 average rating, 254 reviewsNorthside Chicago Favorite with parking!
12–19 Apr
Quick stats about holiday rentals with outdoor seating in Chicago
Total rentals
2.5K properties
Rentals with dedicated workspaces
2K properties have a dedicated workspace
Rentals with a pool
280 properties have a pool
Pet-friendly rentals
890 properties allow pets
Family-friendly rentals
1.6K properties are a good fit for families
Total number of reviews
154K 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 outdoor seating United States
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- Family-friendly rentals Chicago
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- Rentals with outdoor seating Downtown Chicago
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