Vacation rentals with outdoor seating in Ravenswood

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Top-rated outdoor seating rentals in Ravenswood

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Top guest favorite

A gated entryway is visible, featuring a wooden fence painted in a neutral tone. The gate is partially open, leading into a green space lined with trees and plants. The house entrance is seen in the background, with a clear sky above.

Apartment in Edgewater

4.93 out of 5 average rating, 450 reviews

Ravenswood Guest House Annex

The Annex is a private apartment in an 100+ year old wood frame home just north of Andersonville. The Annex is a typical Chicago style 'in-law' garden apartment - located on the first floor of the house where we live - it is bright and clean and well appointed with comfortable furniture. (see pictures). It has large windows that look out on our garden and yard. Our daughter's family also lives on the property in rear coach house. There is easy access to Lake Shore Drive, Evanston and downtown.

Top guest favorite

A cozy living space features a vibrant orange sofa complemented by decorative throw pillows. A dining area with a small table stands beside a fully equipped kitchen. Artwork adorns the walls, while natural light streams through windows, enhancing the inviting atmosphere.

Condo in Lake View

4.99 out of 5 average rating, 102 reviews

Chic & Comfy • Close to Wrigley

Welcome to your comfy, cozy, cheerful hideaway in the beautiful Buena Park!☀️ Buena Park is a little-known gem. Our home is just blocks from the lakefront (4 blocks), Wrigley (6 blocks), and the major L-line in Chicago (1 block)...yet, you'd never know it given how peaceful and serene it is! We live here part-time, so rest assured you'll have everything you need for a comfortable and enjoyable stay. We ask you please respect our place, and that you enjoy the trinkets + personal items we have!

Top guest favorite

An airy studio bedroom features a spacious bed with white linens and decorative pillows. Large windows allow natural light to fill the room, showcasing a cozy sitting area with a small table and chair. Framed botanical artwork adorns the walls, contributing to a calming ambiance.

Guest suite in Lincoln Square

4.99 out of 5 average rating, 384 reviews

Private Lincoln Square one bed+bath studio apt.

Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

Guest favorite

A modern kitchen showcases sleek white cabinetry and a large island with seating for three on black stools. Open shelving displays various glassware. A stainless steel range hood is positioned above the gas cooktop, while natural light fills the space through windows.

Apartment in Edgewater

4.99 out of 5 average rating, 146 reviews

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a new Metra stop at the end of the block and less than 10 miles from the heart of the city, your urban adventure awaits!

Top guest favorite

A cozy living room features a dark blue sofa with decorative pillows, a light brown leather armchair, and a glass coffee table atop a patterned area rug. Two large windows allow natural light to illuminate the space, which is adorned with a gallery of framed artwork on the walls.

Apartment in Lincoln Square

4.97 out of 5 average rating, 112 reviews

Brand new 2 bed 2 bath apartment in Lincoln Square

Nestled on a quiet tree-lined street, this brand new home is 3 houses from the Chicago River. A quick walk to Lincoln Square, a locals-only destination for brunch, shopping, craft beer, and fantastic food. Relax in the secluded primary suite with a massive zero-threshold shower or walk to the nearby grocery stores to cook a gourmet meal in the fully equipped kitchen. Offering plentiful free parking in a central location, plus a short walk to the Brown Line CTA train to anywhere in the city.

Guest favorite

The exterior of a charming coach house is presented, featuring wooden shingles and a well-maintained yard. A circular table with chairs is set on the lawn, accompanied by a green umbrella for shade. Lush bushes border the property, and a wooden fence encloses the yard.

Guesthouse in Lincoln Square

4.88 out of 5 average rating, 327 reviews

Private Coach house near Lincoln Square!

Lovely 625 Sq Ft detached, single-story coach house(100 years old) located in Bowmanville, nestled between Andersonville, and Lincoln Square. This little piece of heaven offers the privacy of a detached home with a fenced oversized yard perfect for puppies to run around in or enjoy a beer from one of our many local breweries. The house provides a full-size kitchen and bath with a walk Less than 1 mile to the closest CTA and 1.5 from Wrigley. Pets Allowed! Bathroom/Shower updated Feb 2025!

Top guest favorite

The bright living area features a grey sofa adorned with colorful cushions. Two teal chairs are positioned nearby, adding a pop of color. Natural light floods the space through oversized windows, highlighting the vibrant artwork on the wall and a modern coffee table at the center.

Apartment in Andersonville

4.95 out of 5 average rating, 572 reviews

Stunning Retro Apartment in Andersonville

Stay in this perfectly situated apartment in the heart of vibrant Andersonville and find out why TimeOut Magazine calls this “The Coolest Neighborhood in the US”. Full of natural light, this 2 bedroom, 1 bath home has generous room sizes, and located on the ground floor of an immaculately kept vintage 4 unit building that has been fully upgraded with modern amenities. Plenty of free parking 24/7. Folks who stay here really will get an authentic Chicago-style experience.

Top guest favorite

A welcoming living area is presented with a mix of plush seating, including a white chair and a vibrant orange sofa. A wooden shelving unit displays decorative items and books. Soft lighting enhances the wooden floor, while light streams through large windows dressed with sheer coverings.

Home in Lincoln Square

4.98 out of 5 average rating, 123 reviews

Entire first floor in Lincoln Square!

First floor of a restored 1903 Victorian in Lincoln Square. The home is spacious with high ceilings throughout and a very open feel. You'll have the whole 1st-floor with access to the backyard with chairs & fire pit. Two bedrooms and an office with additional sleeping options (ask me!). Large dining room & eat-in kitchen. Brand new kitchen & huge new bath! Many short-term rentals in this area are third-floor walk-ups. Make your life easier and stay on the first floor!

Top guest favorite

A charming front porch features a small round table surrounded by two wrought iron chairs. A cozy seating area is adorned with a vibrant red blanket. Flower planters filled with lush greenery and colorful blooms enhance the inviting ambiance, with sunlight filtering through the trees.

Condo in Lincoln Square

4.96 out of 5 average rating, 136 reviews

Best Lincoln Square location. Spacious 2 bedroom

Charming home in an updated 1800's beautiful brick building. High ceilings, spacious, loads of windows and antique furnishings. Located in the heart of Chicago's Lincoln Square. 2 blocks to the El train. Walk to movies, restaurants, bars, parks. Lovely quiet & upscale neighborhood. Bike to the beach & downtown. 2 blocks from Old Town School of Folk Music. Inquire about our Cubs Season Tickets! Space is ideal for adults and families with children over 10 yrs.

Guest favorite

A lounge area features a curvy orange sofa, complemented by a black circular coffee table resting on a textured cream rug. Natural light filters through large windows, illuminating framed wall art with subtle hues. Minimalist decor creates a cozy and inviting atmosphere.

Guest suite in Avondale

4.94 out of 5 average rating, 142 reviews

Logan Square Garden Suite

Creative and quiet light-filled garden unit with lots of books, accompanied by comfortable lounge furniture and touches of nature for cozying up and relaxing after long travel or late nights. This is a perfect space for solo travelers or couples. This is also a great space if you are traveling with a small child or infant. The place is set up much like a hotel room in that it does not have a kitchen but we do provide a mini fridge and Nespresso machine.

Guest favorite

A bright living area is presented with a patterned armchair and a cozy sofa adorned with a colorful throw. A wooden coffee table is positioned in front, while a window with sheer curtains frames the view of the outdoor porch area.

Apartment in Lincoln Square

4.95 out of 5 average rating, 402 reviews

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

Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.

Guest favorite

A comfortable living area features a tufted sofa facing a stylish glass coffee table. A large potted plant and an elegant lamp add warmth, while bright natural light filters through tall windows, enhancing the cozy ambiance. Wall art and decorative elements complete the inviting space.

Apartment in Lincoln Square

4.97 out of 5 average rating, 117 reviews

Paris in Chicago! Elegant vintage apartment.

Elegant vintage apartment with high ceilings and filled with sunlight. Walking distance to public transport, nearby parks, and Lincoln Square cafés and shopping with a European neighborhood feel. Free and easy street parking. Close to Wrigley Field. Very safe neighborhood. LGBTQ and POC welcome. Happy to communicate in English, Italian, Spanish, and French. I look forward to hosting you.