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
23–30 Oct
Home in Chicago
4.98 out of 5 average rating, 206 reviewsWrigleyville Southport Studio
30 Oct – 6 Nov
Home in Chicago
4.97 out of 5 average rating, 357 reviewsGreystone Haven in Logan Square
17–24 Oct
Home in Uptown
4.89 out of 5 average rating, 333 reviewsPrivate 3rd Floor Apartment
19–26 Feb
Home in Avondale
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
27 Dec – 3 Jan
Home in Roscoe Village
4.94 out of 5 average rating, 212 reviewsModern Home RoscoeVillage/Wrigley Free St Parking
18–25 Nov
Home in Forest Park
4.91 out of 5 average rating, 223 reviewsCharming dog friendly 2-Bath Bungalow Near Chicago
23–30 Jun
Home in Chicago
4.95 out of 5 average rating, 129 reviewsChicago Riverhouse summer on our patio!
31 Oct – 7 Nov
Apartment rentals with outdoor seating
Apartment in Chicago
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
31 Dec – 7 Jan
Apartment in Chicago
4.98 out of 5 average rating, 221 reviewsUkrainian Village Garden Retreat
24–31 Oct
Apartment in Lincoln Square
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
10–17 Dec
Apartment in Chicago
4.96 out of 5 average rating, 376 reviewsKing Bed, Huge Spa Shower, Dining Destination
5–12 Jan
Apartment in Wicker Park
4.97 out of 5 average rating, 237 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
10–17 Mar
Apartment in Lake View
4.86 out of 5 average rating, 202 reviewsPrivate Queen Bedroom and En Suite Bath
14–21 Jul
Apartment in Chicago
4.95 out of 5 average rating, 109 reviewsComfortable, modern apartment 20 Min from Downtown
22–29 Nov
Apartment in Chicago
4.96 out of 5 average rating, 164 reviews2BR Centrally Located in Cozy Hip Logan Square
3–10 Oct
Condo rentals with outdoor seating
Condo in Chicago
4.96 out of 5 average rating, 120 reviewsPrivate hot tub - King bed suite - Free parking
27 Jul – 3 Aug
Condo in Chicago
4.9 out of 5 average rating, 136 reviewsEast Garfield Park 2 Bedroom
21–28 Apr
Condo in West Town
5.0 out of 5 average rating, 100 reviewsSpacious 4 Bedroom Condo
16–23 Feb
Condo in Logan Square
4.98 out of 5 average rating, 234 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
4–11 Jan
Condo in Chicago
4.81 out of 5 average rating, 265 reviewsWelcoming 2BR in Chicago's Best Neighborhood!
3–10 Jul
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 Woodlawn
4.9 out of 5 average rating, 192 reviewsA Stones Throw from U Chicago South Campus!
9–16 Nov
Destinations to explore
- 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
- Chicago 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
- Beachfront rentals Downtown Chicago
- 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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