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Holiday rentals with outdoor seating in Cook County

Find and book unique rentals with outdoor seating on Airbnb

Top-rated rentals with outdoor seating in Cook County

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Flat

4.86 out of 5 average rating, 394 reviews

Explore the City from an Elegant, Urban Retreat

- Queen Size bed in the private bedroom for two guests. - Sofa Bed with Full Size mattress for the 3rd and 4th guests (light weight and easy to setup). - Additional portable twin size cot can be set up per request. - Private Bathroom has a ceiling speaker and night light. - Living Room has an HD cinema projector with 100" screen. - A private garden with a gas grill and patio dining table/chairs. - Entry gate and door are Keyless/ Secured Key-coded. - Attached Private Parking space is available per request (subject to availability). - Easy Street Parking: Street parking is zoned (Chicago Residential Zone Parking) and we provide daily zone permits for parking on the street in front of the apartment. - Garden Space offers gas grill for Summer/Fall cookout (Share with two other apartments in the building). Text or phone call for quick reply The apartment is near the popular West Loop and West Town neighborhoods and close to public transit. Downtown parks, museums, and shops are less than two miles away. There's a Divvy Bikes station and a Starbucks across the street. Short walk to public transit ("L", bus, or Divvy bikes) 1 min drive to I-90/94. Less than 2 miles to downtown parks, museums, and shopping destinations. Less than 10 min drive to Lincoln Park, Old Town, and 5 min drive to Wicker Park, and Bucktown.

Guest favourite

Flat

4.92 out of 5 average rating, 180 reviews

iKlektik House Chicago / BlueJay

Enjoy the warm heated floors and check out this home's amazing craftsmanship and artwork. Custom made built-in king size bed. Large custom kitchen, butcher block and claw foot tub in bathroom. WE DO NOT RENT ON "CL" DO NOT WIRE $ IT'S A SCAM The apartment is located in West Town. CLOSE TO THE UNITED CENTER New restaurants and neighborhood favorites, along with cocktail bars and music venues. Metra, Cta {buses and trains} close by. Metra: Western & Hubbard Free Street Parking Right Out Front!

Guest favourite

Home

4.91 out of 5 average rating, 110 reviews

California King Bed | Fast Wi-Fi | 75" Smart TV

Our 3bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful, quiet neighborhood. Built w/ cathedral ceilings, there is plenty of space for 10 people to sleep comfortably (6 beds & several comfy couches), as well as 3 smart TVs (w/ complimentary Hulu & Disney+), an indoor fireplace, a gas grill & large yard (including outdoor games), a desk space, & more. Enjoy close access to main roads & large stores (Costco, Walmart, hardware stores, etc.)!

Flat

4.84 out of 5 average rating, 275 reviews

4BDRM Gorgeous Apt Pilsen Private Prking Available

Stylish Retreat for Groups in Vibrant Pilsen Welcome to our 7-room home in lively Pilsen, perfect for families and groups of up to 10. Enjoy spacious comfort in a prime location. Explore vibrant murals, visit Simone's bar, and savor Sunday brunch at Dusek's. Catch a concert at Thalia Hall or sing at nearby karaoke or grab dim sum. Conveniently located just down the street from Chinatown and close to McCormick Place. Ideal for conventions and city adventures. Book now for an unforgettable stay!

Guest favourite

Apartment

4.94 out of 5 average rating, 138 reviews

711 The Penthouse

Luxurious upscale Duplex Penthouse-River West neighborhood in downtown Chicago! Newly rehabbed and updated interior design that is mind blowing. Over 5600 sq ft. Features 5 bedrooms, 2.5 baths, 3 largeTVs with sonos sound system, game room!!. Near CTA Blue Line, close to the best dining and attractions of Chicago! Two large living areas perfect for hosting small events, bachelor(ette) parties, bridal or baby showers, work/travel, and family reunions. Rooftop with beautiful view of the skyline!

Guest favourite

Flat

4.96 out of 5 average rating, 135 reviews

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Location! Location! Location! Prime Wicker Park Location on Milwaukee! This spacious, cool, vibrant, eclectic, fully equipped apartment is close to everything, making it easy to plan your visit. Bright top floor unit with a private patio to just chill and unwind or walk downstairs and your literally in the heart of Wicker Park. Super easy access to downtown nightlife/lake/museum all within 15 minutes and super easy commute to O'hare. CTA busses all around and a 2 minute walk to the Blue Line.

Guest favourite

Home

4.91 out of 5 average rating, 173 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Say "WOW" in this top floor, IMMACULATE SPACIOUS with cozy FIREPLACE + ROOFTOP overlooking skyline! Open 2-story layout w/7 bed options, 3 bathrooms, private rooftop with skyline. Luxury flooring, soaring high ceilings, fully-stocked kitchen + huge island, keyless entry, 2 HD TVs, & outdoor grill. Perfect for SPECIAL OCCASIONS! Next to all Wrigley bars & restaurants. Train to Downtown <12 mins. Private parking for rent. As a "GUEST FAVORITE" we boast >1220 5-star reviews across listings!

Guest favourite

Apartment

4.94 out of 5 average rating, 136 reviews

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Escape into this prime, Chicago Penthouse! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Private, spacious roof deck viewing the entire Chicago skyline! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out - Designated parking spot! - Steps away from blue line Damen station (800 feet)

Home

4.91 out of 5 average rating, 118 reviews

Peaceful & Private Hot Tub Vacation Home Getaway

A Rare gem 💎in the heart of Homewood. This Quaint 2-bedroom remodeled home is charming, sophisticated and discrete. It is minutes away from the Metra station, golf course and downtown Homewood shops. The energy is very calm and quiet ☯️. This is the home away from home where details are everything and the pictures do not capture the essence of this luxurious space. Experience the love, the joy and the peace that continues to leave its mark. Peace and Love - Michael and KP💞

Flat

4.82 out of 5 average rating, 169 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

Relax with the whole family or explore the city with friends at this peaceful and spacious 3-bd/1.5ba condo tucked on a quiet, tree-lined street. Includes one (1) free parking space, plus plenty of unmetered parking on st. Minutes away notable hospitals, both Northwestern, and Loyola Universities. Travel via CTA bus stop at the corner. Only 30min drive from downtown Chicago. PET & 420 FRIENDLY!

Guest favourite

Yurt

4.97 out of 5 average rating, 103 reviews

Glamping Yurt&RV-Game Room-Pool-Sauna-Hotub Court

Glamping Experience to the NEXT LEVEL! Opened April - Nov. Contact during off season. Mini Resort Includes: RV w/bathroom - 2 beds & sofa sleeper 20' Safari Yurt - 3 beds Game Room w/bathroom 1 bed & sofa sleeper Gazebo w/2 twin beds Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs seasonally Mini Golf lanes Basketball, Volleyball, Pickleball court

Flat

4.88 out of 5 average rating, 240 reviews

Bunks and 4 post bed apt.

The perfect jumping off point for exploring Chicago, we are located in hidden gem Berwyn, just 2 blocks from the train station. Child-friendly, free parking. Our home is also the site of a micro-flower farm, with pocket forest, native garden, fruit trees and kids play house. Our first floor apartment also has a crib, high chair, bunkbeds and free street parking.

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Popular amenities for outdoor seating rentals in Cook County

Free parking on premises

Air conditioning

House rentals with outdoor seating

Guest favourite

Home

4.85 out of 5 average rating, 40 reviews

The Banksy-King Bed-Firepit-Rooftop-United Center

Guest favourite

Home

4.87 out of 5 average rating, 15 reviews

Enamored in Elmhurst

Guest favourite

Home

4.91 out of 5 average rating, 76 reviews

Remodeled | Game room | Fire Pit | 5 Min to Zoo

Guest favourite

Home

4.92 out of 5 average rating, 266 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

Home

4.82 out of 5 average rating, 109 reviews

Maywood Relaxation

Guest favourite

Home

4.95 out of 5 average rating, 39 reviews

Gorgeous and Luxurious 3 BR Home

Guest favourite

Home

5 out of 5 average rating, 7 reviews

3 x Queen Beds + Pull Out Sofa Bed - No Stairs !

Guest favourite

Home

4.94 out of 5 average rating, 125 reviews

BoHo House - A Chic, 1903 Chicago Workers Cottage

Apartment rentals with outdoor seating

Guest favourite

Flat

4.95 out of 5 average rating, 129 reviews

Bohemian Moto Inn

Flat

4.72 out of 5 average rating, 116 reviews

The Biddle House (#1)

Guest favourite

Flat

4.91 out of 5 average rating, 123 reviews

Modern 3BR with Private Rooftop & Free Parking

Guest favourite

Flat

4.98 out of 5 average rating, 103 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

Flat

4.92 out of 5 average rating, 151 reviews

Executive Apartment on Lake Michigan with parking

Guest favourite

Flat

4.92 out of 5 average rating, 181 reviews

Large sunny 3BR apt. in downtown Oak Park

Guest favourite

Flat

5 out of 5 average rating, 109 reviews

Spacious 2 Bedroom in the heart of Lakeview!

Guest favourite

Flat

4.97 out of 5 average rating, 138 reviews

Inviting 2 Bedroom Apartment in Roscoe Village

Apartment rentals with outdoor seating

Guest favourite

Apartment

4.9 out of 5 average rating, 107 reviews

Convenient & Spacious 3BR Condo w/Free Parking

Guest favourite

Apartment

4.92 out of 5 average rating, 107 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

Guest favourite

Apartment

4.94 out of 5 average rating, 105 reviews

Urban Oasis | Great for Families w/ Kids

Guest favourite

Apartment

4.91 out of 5 average rating, 100 reviews

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

Guest favourite

Apartment

4.84 out of 5 average rating, 423 reviews

Authentic Condo steps from Wrigley Field!

Guest favourite

Apartment

4.98 out of 5 average rating, 109 reviews

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

Guest favourite

Apartment

4.99 out of 5 average rating, 146 reviews

Spacious 4 Bedroom Condo

Guest favourite

Apartment

4.98 out of 5 average rating, 127 reviews

Luxurious River North 3BR/2BA- Free Onsite Parking

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