Holiday rentals with outdoor seating in Chicago Loop

Find and book unique rentals with outdoor seating on Airbnb

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Popular amenities for outdoor seating rentals in Chicago Loop

Apartment rentals with outdoor seating

Guest favourite

Flat in Chicago

4.91 out of 5 average rating, 185 reviews

Lovely City Apartment-Near Downtown-Food-Train!

10–17 May

$201 SGD per night
Guest favourite

Flat in Cicero

4.98 out of 5 average rating, 201 reviews

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

17–24 Nov

$168 SGD per night
Guest favourite

Flat in Chicago

4.96 out of 5 average rating, 161 reviews

2BR Centrally Located in Cozy Hip Logan Square

8–15 Nov

$168 SGD per night
Guest favourite

Flat in Lincoln Square

4.96 out of 5 average rating, 321 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

28 Sep – 5 Oct

$181 SGD per night
Guest favourite

Flat in Chicago

4.96 out of 5 average rating, 371 reviews

King Bed, Huge Spa Shower, Dining Destination

1–8 Jan

$236 SGD per night
Guest favourite

Flat in Chicago

4.85 out of 5 average rating, 160 reviews

Your brand new Chicago suite (unit 1F)

$85 SGD per night
Guest favourite

Flat in Lincoln Square

4.78 out of 5 average rating, 269 reviews

Cozy Garden-Subterranean Apartment

24 Sep – 1 Oct

$140 SGD per night
Superhost

Flat in Pilsen Historic District

4.82 out of 5 average rating, 427 reviews

Eclectic Artist Designed Sanctuary Heart of Pilsen

1–8 Oct

$226 SGD per night

Apartment rentals with outdoor seating

Guest favourite

Apartment in Chicago

4.88 out of 5 average rating, 234 reviews

2 King Bed Condo Easy Downtown Free Street Parking

5–12 Sep

$212 SGD per night
Guest favourite

Apartment in Little Italy

4.96 out of 5 average rating, 118 reviews

Private hot tub - King bed suite - Free parking

4–11 Oct

$373 SGD per night
Guest favourite

Apartment in Chicago

4.9 out of 5 average rating, 135 reviews

East Garfield Park 2 Bedroom

4–11 Nov

$183 SGD per night
Guest favourite

Apartment in North Center

4.91 out of 5 average rating, 119 reviews

Spacious & Modern Family Friendly North Center Apt

24–31 Jan

$209 SGD per night
Guest favourite

Apartment in Woodlawn

4.9 out of 5 average rating, 190 reviews

A Stones Throw from U Chicago South Campus!

6–13 Jan

$178 SGD per night
Guest favourite

Apartment in Chicago

4.91 out of 5 average rating, 246 reviews

Old Town Pied-à-Terre w/Pvt Terrace and Parking

8–15 Sep

$628 SGD per night
Guest favourite

Apartment in Logan Square

4.98 out of 5 average rating, 232 reviews

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

7–14 Sep

$297 SGD per night
Guest favourite

Apartment in Chicago

4.96 out of 5 average rating, 112 reviews

Best Lincoln Square location. Spacious 2 bedroom

6–13 Jan

$272 SGD per night

Quick stats about holiday rentals with outdoor seating in Chicago Loop

  • Total rentals

    140 properties

  • Rentals with a pool

    80 properties have a pool

  • Pet-friendly rentals

    60 properties allow pets

  • Family-friendly rentals

    60 properties are a good fit for families

  • Total number of reviews

    10K reviews

  • Nightly prices starting at

    $27 SGD before taxes and fees

Destinations to explore