Holiday rentals with outdoor seating in Downtown Chicago
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Downtown Chicago
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Downtown Chicago outdoor seating rentals
Holiday House Rentals with Outdoor Seating
Home in Berwyn
4.91 out of 5 average rating, 242 reviewsPrivate apartment with retro vibe
20 – 27 July
Home in Uptown
4.89 out of 5 average rating, 333 reviewsPrivate 3rd Floor Apartment
11 – 18 Feb
Home in Roscoe Village
4.94 out of 5 average rating, 212 reviewsModern Home RoscoeVillage/Wrigley Free St Parking
4 – 11 Mar
Home in Chicago
4.97 out of 5 average rating, 357 reviewsGreystone Haven in Logan Square
17 – 24 Oct
Home in Chicago
4.98 out of 5 average rating, 206 reviewsWrigleyville Southport Studio
25 Nov – 2 Dec
Home in Forest Park
4.91 out of 5 average rating, 224 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
23 – 30 June
Home in Chicago
4.95 out of 5 average rating, 129 reviewsChicago Riverhouse summer on our patio!
22 – 29 Dec
Home in Avondale
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
20 – 27 Apr
Apartment rentals with outdoor seating
Apartment in Lake View
4.86 out of 5 average rating, 202 reviewsPrivate Queen Bedroom and En Suite Bath
7 – 14 July
Apartment in Forest Park
4.98 out of 5 average rating, 285 reviewsWalk to Oak Park from Our Sunny Turn of the Century Apt
4 – 11 Dec
Apartment in Chicago
4.96 out of 5 average rating, 376 reviewsKing Bed, Huge Spa Shower, Dining Destination
5 – 12 Jan
Apartment in Chicago
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
2 – 9 Dec
Apartment in Chicago
4.96 out of 5 average rating, 165 reviews2BR Centrally Located in Cozy Hip Logan Square
29 Apr – 6 May
Apartment in Chicago
4.95 out of 5 average rating, 109 reviewsComfortable, modern apartment 20 Min from Downtown
1 – 8 Feb
Apartment in Andersonville
4.98 out of 5 average rating, 251 reviewsAndersonville Cozy 1 bedroom basement suite
4 – 11 Jan
Apartment in Chicago
4.97 out of 5 average rating, 237 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
23 Feb – 2 Mar
Condo rentals with outdoor seating
Condo in Chicago
4.96 out of 5 average rating, 120 reviewsPrivate hot tub - King bed suite - Free parking
18 – 25 Aug
Condo in Chicago
4.9 out of 5 average rating, 136 reviewsEast Garfield Park 2 Bedroom
6 – 13 Nov
Condo in Chicago
4.98 out of 5 average rating, 234 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
7 – 14 Jan
Condo in Chicago
5.0 out of 5 average rating, 100 reviewsSpacious 4 Bedroom Condo
16 – 23 Feb
Condo in Chicago
4.9 out of 5 average rating, 192 reviewsA Stones Throw from U Chicago South Campus!
9 – 16 Nov
Condo in Chicago
4.86 out of 5 average rating, 191 reviewsBold Ukrainian Village 2 Bedroom w/Garage Parking
19 – 26 Nov
Condo in Chicago
4.88 out of 5 average rating, 235 reviews2 King Bed Condo Easy Downtown Free Street Parking
29 Oct – 5 Nov
Condo in Chicago
4.98 out of 5 average rating, 256 reviewsNorthside Chicago Favorite with parking!
22 Feb – 1 Mar
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Accommodation & holiday rentals
- Lake Michigan Beach Accommodation & holiday rentals
- Saugatuck Accommodation & holiday rentals
- Evanston Accommodation & holiday rentals
- Holland Accommodation & holiday rentals
- South Haven Holiday rentals
- Naperville Accommodation & holiday rentals
- South Side Accommodation & holiday rentals
- South Bend Accommodation & holiday rentals
- New Buffalo Holiday rentals
- Chicago Accommodation & holiday rentals
- Rentals with outdoor seating United States
- Rentals with outdoor seating Chicago
- Family-friendly rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Condo rentals Downtown Chicago
- Rentals with pools Downtown Chicago
- Kid-friendly rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with a patio Downtown Chicago
- House rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with a fire pit Downtown Chicago
- Townhouse rentals Downtown Chicago
- Monthly Rentals Downtown Chicago
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- Loft rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with a home theatre Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with outdoor seating Milwaukee
- Rentals with outdoor seating Lake Geneva
- Rentals with outdoor seating Illinois
- Rentals with outdoor seating Cook County
- Yurt Rentals United States
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