Guesthouse vacation rentals in North Side

Guesthouse in Logan Square

The living area features a wall-mounted TV opposite a light-colored loveseat and a blue armchair. A small round coffee table is situated on a textured gray rug. Natural light enters through the two windows, with modern framed art and a floor lamp adding character.

4.98 out of 5 average rating, 401 reviews

Private coach house near transit shops & nightlife

This renovated coach house comfortably accommodates 3 adults but can sleep 4. Only a 7 minute walk from the "L" train (CTA blue line to O'Hare airport & downtown). Close to Chicago's Wicker Park and Logan Square neighborhoods with lots of nightlife and dining options within a 10-15 minute walk. The two story, ~750 sqft space features a bedroom and office upstairs; the ground floor has a combined kitchen/living room and one bathroom. 4 guest limit based on city of Chicago occupancy ordinances.

LocationFamilyAir conditioning

A bright living area with a sloped ceiling features a comfortable blue sofa and light-colored armchairs. A small marble-top table is set with two cups. A desk is positioned near a window, and a decorative rug adds warmth to the hardwood floor.

4.97 out of 5 average rating, 133 reviews

Oak Park cozy carriage house-lovely, walkable area

Our comfortable, stylish retreat has everything you need to relax and recharge. Whether you are visiting to explore all that beautiful Oak Park and downtown Chicago offer or desire a peaceful space to work. -> Quiet, walkable street near popular cafes, restaurants, taverns, parks, historic homes -> Steps from the "L" Blue Line Oak Park station -> Stocked w/ snacks + gourmet coffee/tea set-up (grinder, AeroPress, and Keurig) -> Onsite off-street parking -> A/C + heat -> garden sitting area

LocationValueBackyard

Superhost

A spacious bedroom is furnished with a large bed featuring a gray and white patterned blanket. Art pieces are displayed on the wall above the bed, and two bedside lamps with warm light sit on either side. A bold, geometric area rug adds texture to the space.

4.91 out of 5 average rating, 268 reviews

Gallery Loft of Oak Park #1 Top Host in IL

Gallery Loft of Oak Park <a href="https://news.airbnb.com/the-number-one-new-host-in-each-us-state/">2021 #1 Top Host in Illinois</a> is a Chicagoland gem near the birthplace of Ernest Hemingway, Frank Lloyd Wright Home/Studio. 2nd story flat furnished in vintage mcm style, featuring local artists. Walking distance to live music (Fitzgerald's, Friendly Music Community), and restaurants. Firepit access, easy street parking and kitchen well stocked. Private porch. Perfect long/short term stays.

ValueFamilyPool

Guesthouse in Rogers Park Township

A spacious living area features a stone fireplace adorned with a mounted moose head. Natural light filters through the stained glass windows, illuminating potted plants. Black chairs and a neutral sofa are positioned around a wooden coffee table, creating a cozy gathering space.

4.95 out of 5 average rating, 152 reviews

A bit of the North Woods on Chicago's North Side!

Looking to get away from it all but not TOO far away? Ours is a quiet, screen-free property perfect for a writer’s or artist’s retreat. NU/Loyola parents or alums, stay here when you visit your kids/alma mater. Fantastic renovated livery barn with lots of light, privacy and amenities. Located in Rogers Park, a short walk to Metra and the Red line. Ample street parking nearby. Created for comfort with a splash of Swedish design, enjoy the deck overlooking a tree-filled garden and waterfall.

FamilyValueComfort

4.94 out of 5 average rating, 141 reviews

The historic manor house features a rich red brick facade adorned with lush green ivy. The spacious porch extends from the building, complemented by well-maintained gardens that enhance the inviting exterior. Large windows provide ample natural light, creating an open and airy ambiance.

Guesthouse in Evanston

Historic Coach House in Evanston Near Beach & Town

Stay in the Coach House of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire coach house which is renovated and includes a large bedroom with king bed and desk, a sun-filled living room/dining room, a full bath with claw-foot soaking tub and shower and a kitchen with amenities. The space can be equipped with an air mattress for an extra guest. Also available is a 3rd floor guest suite in the main house.

ValueFamilyParking

5.0 out of 5 average rating, 101 reviews

The exterior view of the property is framed by lush greenery, including small trees and ornamental plants. A stone pathway leads to the entrance, which features a light-colored door. The building's soft hues complement the natural surroundings under a clear blue sky.

Guesthouse in Evanston

Mr. Hughes’ Attic, an 80s-themed coach house

Welcome to Mr. Hughes' Attic, a private coach house that pays homage to John Hughes (who filmed many of his movies nearby!) Located in NW Evanston, your stay includes a queen bed, full kitchen, laundry, full bath, dedicated workspace, private balcony, free parking, streaming TV, and more. We're a short walk to Central St shops, restaurants and the Metra train, a five-minute drive to Northwestern, and less than 30 minutes to Chicago. Not wheelchair or ADA accessible. License# STR004.

LocationFamilyAir conditioning

Guesthouse in Wicker Park

A landscaped garden patio is illuminated by soft lighting, highlighting a central tree and neatly arranged plants. An outdoor dining table with several chairs stands on stone paving, creating a welcoming space for relaxation. The brick facade of the coach house is visible in the background.

4.98 out of 5 average rating, 101 reviews

Coach House with Garage Parking & EV Charging

Immerse in solar-powered serenity amidst the bustling restaurant, shopping and nightlife scene of the Wicker Park neighborhood of Chicago. Large, loft-like and super sunny one bedroom includes full kitchen with new appliances, landscaped garden patio, and EV charging in an enclosed and attached garage space. All powered by a full array of high-efficiency rooftop solar panels. Five minute walk to the Damen Blue Line and the 606 Elevated Trail for cyclists and runners.

FamilyValueCheck-in

4.88 out of 5 average rating, 390 reviews

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 Chicago

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 are Allowed!

LocationFamilyNearby

4.93 out of 5 average rating, 163 reviews

The exterior of the vintage garage apartment is shown, featuring a bright yellow facade with two white garage doors. A large window is positioned above the doors, with greenery surrounding the property, contributing to the charming appearance.

Guesthouse in Villa Park

Eclectic Coach House Apartment

Vintage Charmer! 1935 Sears Craftsman Coach House garage apartment. Beautiful safe neighborhood surrounded by historic homes and just steps from the Illinois prairie path, parks, brewery's/bars, restaurants and more! With an eclectic boho chic vibe, featuring full kitchen and on site private washer/dryer. Overlooking an accessible lovely backyard! Close to airports and easy access to public transportation/major highways. Just 30 min from the Chicago Loop!

FamilyValueAmenities

Guesthouse in Roscoe Village

A cozy living area features a deep blue sectional sofa with decorative cushions. Natural light enters through two large windows, framed by dark curtains. Light-colored walls are adorned with framed artwork, enhancing the room's inviting ambiance.

4.91 out of 5 average rating, 210 reviews

The Roscoe Village Guesthouse

The Guesthouse is located in a village within the city of Chicago. We are in the heart of Roscoe Village and walking distance to the CTA brown line train. We are less than 1 mile west of Wrigley Field and a 20 minute train ride to downtown Chicago. Right outside your door are restaurants, boutique shopping and cafe's. Plenty of free street parking around the house. I offer this unique & personal space to guests when I am away.

LocationFamilyNearby

An open living area is highlighted by a spacious dark sofa adorned with decorative cushions, complemented by a wood coffee table. A large, comfortable bed occupies one side, while a dining area with a glass table and chairs is visible. Art pieces are displayed on the walls.

4.99 out of 5 average rating, 163 reviews

Stylish Coachhouse in lovely Oak Park!

Enjoy the privacy and artistry of your very own coachhouse. The interior is a personalized mix of artistic, industrial and farmhouse. Cool colors, personalized details and local art included. You have your own washer, dryer, complete kitchen, and private patio space. Walk the lovely neighborhood, to the L train, or even to a local brewery.

ValueLocationIndoor spaces

An inviting living area features a white couch paired with a dark coffee table, facing a flat-screen TV. The modern kitchen showcases sleek cabinetry, a stainless steel refrigerator, and a central island with bar seating, lit by overhead lighting.