Holiday rentals with a patio in Downtown Chicago

Find and book unique Holiday Accommodation with Outdoor Verandahs on Airbnb

Top-rated Holiday Accommodation with Outdoor Verandahs in Downtown Chicago

Guests agree: These Holiday Homes with Outdoor Verandahs are highly rated for location, cleanliness and more.

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Guest favourite

Rental unit in Chicago

4.89 out of 5 average rating, 92 reviews

Adorable Private Edgewater Suite

Cozy exposed brick, garden unit on a quiet street, perfect for relaxing after a night out in the city! Comfy, queen-sized bed, full kitchenette and gated private side entrance so its the perfect spot for your trip to Chicago! We are right by the exciting nightlife of Andersonville and a 10 minute walk to the beach/start of the Lakefront trail. Public Transit is close and easily accessible, the redline "L" can get you downtown in a half-hour train ride. Close to Loyola University, Go Ramblers!

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Home in Highland Park

5 out of 5 average rating, 28 reviews

Sanctuary on the Ravine

Take it easy at this unique and tranquil get away, walking distance to Ravinia and Beaches 3 Blocks.This historic, beautifully decorated and well maintained home has a lovely, peaceful & serene setting. Multiple indoor and outdoor seating arrangements. Fully stocked kitchen that opens to family room looking out onto several multilevel brick patios and a quiet, private ravine. The extra large living room has a down feathered sectional couch that seats up to 10 people. No parties or gatherings

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Rental unit in Chicago

4.7 out of 5 average rating, 20 reviews

Minimalistic Avondale - 3 bedrooms 1 bathroom

Come have a relaxing stay in a Modern Minimalistic apartment in the center of the bustling Logan Square neighborhood. With 3 bedrooms each having full-sized beds, a bathroom and plenty of space, it is perfect for a vacation. Nearby there are star studded restaurants such as the Sipping Turtle, Warlord Steakhouse, Lula Cafe, Ryu BBQ, Loaf lounge, Mother's Ruin, Poke Okie, and Taco's Tequilas to name a few. Walking distance to 2 CTA train stations and stone throw away from the I-94 expressway.

Guest favourite

Rental unit in Chicago

4.94 out of 5 average rating, 72 reviews

Loyola & Lake -3br/2bth close to the Lake & Loyola

Amazing lake views from 2 outdoor spaces! This spacious 3 bedroom, 2 bath unit has a large front balcony looking out to the lake and also a rear deck with lake views as well. The unit was recently renovated and has updated kitchen, bath & lots of entertaining space. In unit laundry and detergent included. Lots of books and games to keep you entertained! Walking distance to restaurants and bars. Starbucks is at the end of the block. Kayaks/paddle boards available for rent (May 1-Oct 15).

Guest favourite

Rental unit in Chicago

4.93 out of 5 average rating, 143 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Guest favourite

Bungalow in Chicago

4.92 out of 5 average rating, 12 reviews

Located on Beautiful and Quite Boulevard!

Welcome to The Boulevard A spacious house recently updated located at the beginning of the beautiful quite boulevard. The house is on beautiful Wrightwood Neighborhood Greenway! This house is centrally located 5 minutes away from Metra train station ( Healy Station) that will get you downtown in 15 minutes. Check with Metra for train times. Drive Downtown in 20 minutes(no traffic), O'Hare airport, West Loop. 20 mins to Lakeview, Wrigleyville, Boystown, Logan Square, Bucktown & Wicker Park.

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Home in Oak Park

4.9 out of 5 average rating, 58 reviews

A Comfortable Stay While You are Away in Oak Park

Welcome to this Oak Park home, conveniently minutes from the main expressway, train station, downtown Chicago, and the Medical Center. This entire Oak Park house is ideal for travelers seeking a tranquil and welcoming space to unwind in after a long day, medical professionals, visiting patients at the Medical Center, and families needing long-term housing. The residence is minutes from downtown Oak Park and the historical landmarks of Frank Lloyd Wright's home and studio.

Guest favourite

Home in Westmont

4.89 out of 5 average rating, 74 reviews

Lil Westmont Cottage whole house and enclosed yard

Perfect for 1 - 6 in quaint Westmont. Decor is vintage chic with a focus on retro arts and collectibles. Cozy blankets and whimsical art adorn the walls. Perfect for folks who love cute quaint CLEAN and comfy not Kondo! A place to call home where the barn door closes off the Living room. A dinner for 6 in the quaint dining area. Laundry room in the home. New Grill for Summer 2024, out door furniture. Beyond pet friendly we have many accessories for Dogs.

Guest favourite

Home in Elmhurst

5 out of 5 average rating, 27 reviews

Big Family Home with 4 King Beds

Experience ultimate luxury at our exclusive property. Nestled in a prime location, this meticulously designed retreat offers opulent furnishings, panoramic views, and bespoke amenities. Ideal for discerning travelers and work travelers seeking sophistication and comfort, indulge in a private sanctuary where every detail exceeds expectations. Discover the epitome of elegance with us and create unforgettable memories in this exquisite haven.

Guest favourite

Rental unit in Forest Park

4.86 out of 5 average rating, 206 reviews

Home in Forest Park downstairs

Enjoy a private ground floor apartment which is centrally-located with easy access , to the city. You will have a functional kitchen, laundry facility outside your back door and fast internet. Forest Park is located about 20 minutes from downtown Chicago and about 30 minutes from O’Hara international airport. You are within walking distance of many boutiques, restaurants, parks and also public transportation.

Guest favourite

Rental unit in Palatine

4.96 out of 5 average rating, 152 reviews

Huge Sofa-King Bed-Retro-Private Deck-Downtown Pal

MId Century Modern 1 Bedroom With Private Entrance in Downtown Palatine! Over 140 5 Star Reviews on Airbnb ★★★★★ "I cannot say enough about this wonderful little apartment." Janell - July 2024 700sf Retro Apartment with a King Bed & Private Outdoor Space. Safe Off Street Parking. Just Steps to Public Transportation, Bars & Restaurants.