Holiday rentals with a patio in Downtown Chicago

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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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Rental unit in Chicago

4.74 out of 5 average rating, 19 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, 71 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

4.94 out of 5 average rating, 140 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

4.91 out of 5 average rating, 11 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.

Guest favourite

Home in Lombard

5 out of 5 average rating, 14 reviews

Spacious Home in Chicago Suburbs

Enjoy your stay in Chicagoland in this gorgeous, newly updated home. After a full day of sightseeing in the Windy City or hitting the local shops and attractions, this is a restful homebase to return to. The spacious fenced-in backyard and patio, a comfortable and tastefully furnished basement, and the full kitchen with amenities provide the perfect environment to unwind. You’ll find plenty of seating, sleeping accommodations for nearly a dozen, and an open layout that fosters connection.

Superhost

Home in Oak Park

4.9 out of 5 average rating, 58 reviews

A Comfortable Stay While You are Away

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

4.9 out of 5 average rating, 72 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, 21 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, 196 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.

Superhost

Rental unit in Evanston

4.82 out of 5 average rating, 164 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

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.