Vacation rentals in North Side

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Top-rated vacation rentals in North Side

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.

Apartment in West Rogers Park

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

FamilyLocationIndoor spaces

4.99 out of 5 average rating, 119 reviews

Guest favorite

The living area features a comfortable sofa adorned with colorful cushions, positioned beside a unique wooden coffee table. A striking piece of wall art adds visual interest, while a dining area with modern chairs is visible in the background, complemented by potted plants.

Guest suite in Portage Park

Peaceful Portage Park Apartment

You have the entire apartment all to yourself (kitchen, bathroom, 2 bedrooms and an office). Shared backyard. Portage park is located about halfway between O’hare airport and downtown. It is one of the safest neighborhoods in Chicago. Parking is easy! We’re 2 blocks away from a park (dog park, playground, walking/running path, tennis courts, indoor and Olympic sized outdoor pool). Fairly close to coffee shops and good places to eat We are family friendly House trained dogs are ok : $10/night

ValueFamilyIndoor spaces

4.94 out of 5 average rating, 476 reviews

Top guest favorite

A private outdoor patio is surrounded by wooden fencing, featuring a glowing sofa and two chairs placed on a patterned rug. A small table holds a plant, while greenery adds a natural touch to the tranquil setting, under a colorful sky at dusk.

Home in Chicago

The Chicago River House – GIANT wall projector!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

FamilyLocationHeating

4.96 out of 5 average rating, 213 reviews

Guest favorite

A spacious bedroom features a neatly made bed with a soft, gray comforter. A large television is mounted on the wall above a wooden table adorned with flowers. A mirror is positioned to the side, and a closet is visible in the background.

Apartment in Jefferson Park

2 BR/1 BA with Separate Entrance

The whole group will enjoy easy access to everything from this centrally located place. + Very Safe Area and Conveniently Located! + Private Entrance and Floor + Private Bathroom with two Private bedrooms + Updated all brand new equipment + Free Wifi & Smart TV in each room + 5 min Walk to Metra and Bus Stop. + 10 min drive to O'hare and Downtown + Free and Easy Street PARKING. + Short Walk to Convenience Stores + Bedroom with Fan, AC, and Heat + Fully Stocked Kitchen + Keyless Self Check-in

FamilyLocationCheckout

4.77 out of 5 average rating, 151 reviews

Superhost

Apartment in Jefferson Park

Modern 2 bdrm apt near O'hare-Downtown. King bed.

Step into the vibrant Gladstone Park neighborhood, a mere mile from the blue line. Picture yourself minutes away from O'Hare airport, the Rosemont Convention Center, Fashion Outlet mall, and the thrilling Rosemont Casino. Your spacious haven awaits – a sunny 2-bedroom, 1-bath apartment, brimming with all essential amenities. Feel the convenience with in-unit washer and dryer, hassle-free parking on-site, and free street parking. Don't miss out – book your stay now for a colorful experience.

FamilyLocationNearby

4.85 out of 5 average rating, 152 reviews

Top guest favorite

The exterior of a charming historic bungalow is framed by lush greenery and vibrant flower beds. Large windows provide natural light and a view into the inviting interior, while the brick facade complements the surrounding landscaped garden.

Apartment in Albany Park

Cozy Bungalow Getaway

This comfy, cool, garden-level apartment is nestled in a friendly historic Chicago bungalow neighborhood. It’s close to universities (Northeastern and North Park), LaBagh Woods (hiking/biking trails), Gompers Park pool, park and lagoon, O'Hare Airport (20 mins away) and diverse restaurants and entertainment, some walkable, some a short Uber/Lyft away. Easy expressway, transit and bike trail access. Perfect for solo adventurers, couples, students, visiting families, and business travelers.

ValueFamilyIndoor spaces

4.99 out of 5 average rating, 82 reviews

Top guest favorite

A contemporary loft bedroom features a spacious bed with a light grey quilt. Exposed brick walls complement framed vintage Chicago artwork. Soft lighting is provided by string lights near the window. A green plant adds a touch of nature, while dark wood accents create warmth.

Loft in Lake View

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

LocationValueAir conditioning

4.96 out of 5 average rating, 608 reviews

Top guest favorite

Home in Chicago

New Home | O'Hare Airport

• Single Family Home | 2 Floor • Basement | Master Suite! • 4 Beds | Sleeps 8! • Commute to O'hare: 16 min (drive) • Metra Train to Downtown Chicago • Easy Street Parking • Family Friendly | Peace at Night • Building outdoor video surveillance • Noise monitoring equipment. • Kitchen is stocked | cookware | utensils • Washer | Dryer | Dishwasher in unit (free) • Rosemont Entertainment District!! • Rideshare(Uber/Lyft) • Safe, working class neighborhood

LocationValueKitchen

5.0 out of 5 average rating, 31 reviews

Guest favorite

A comfortable living area is furnished with a tan sectional couch and a small coffee table. A vibrant area rug adds warmth to the hardwood floors. Natural light filters through windows, illuminating wall art and a nearby plant, creating an inviting space.

Apartment in Portage Park

Cozy Jefferson Park 2BR Apt

A lovely 2nd floor apartment flooded with natural light in a 2-unit building located in Jefferson Park. Conveniently located near O’hare airport, filled with small businesses, dive bars, and family-owned restaurants. Downtown Chicago will take 20-40 minutes, depending on traffic. My partner and I live in the unit below and can answer any questions you may have throughout your stay. We have created a warm and safe place for all to feel welcome!

LocationValueGetting around

4.95 out of 5 average rating, 147 reviews

Top guest favorite

The entrance features a welcoming gray wooden deck with steps leading up to the door, framed by a white railing. A brick facade and large window enhance the home's charming exterior, while surrounding greenery adds a touch of nature.

Apartment in Norwood Park

Charming Chicago Apartment • Near O’Hare + Transit

This upstairs 1‑bedroom apartment is your quiet, bright home base just 10 minutes from O’Hare Airport and near the Blue Line for easy city access. Enjoy a full kitchen, fast Wi‑Fi, king bed, and Smart TV for relaxing evenings. • Private balcony seating • Dedicated workspace & fast Wi‑Fi • King bed + blackout curtains • Self‑check‑in + private entrance While there’s no in‑unit laundry, optional wash‑and‑fold service ($25/load) is available.

LocationFamilyCondition

4.94 out of 5 average rating, 307 reviews

Top 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 Ravenswood

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.

LocationValueSleep quality

4.95 out of 5 average rating, 444 reviews

Top guest favorite

A two-story brick home features a welcoming front porch with a stoop and entrance framed by tall windows. Lush greenery and vibrant flower beds add color to the exterior, enhancing the inviting presence of the residence.

Home in Chicago

Big house in the BEST Location!

Spacious 2-story home near O’Hare & Rosemont. Includes 3 bedrooms, 2.5 baths, full kitchen, living & dining areas. Smart TVs in master, kitchen & living room. High-speed WiFi, private deck, and individual room thermostats. No shared spaces, basement & garage not included. Easy access to public transport & free street parking. Ideal for families, work trips, or exploring the Chicago area.

FamilyLocationCleanliness

4.97 out of 5 average rating, 70 reviews