Family-friendly vacation rentals in Norwood Park

4.88 out of 5 average rating, 409 reviews

The spacious living area features a comfortable seating arrangement with a contemporary sofa and an armchair. A wooden coffee table sits in the center, with a television mounted on the wall above a rustic chest of drawers. Natural light filters through the window covered with sheer curtains.

Guest suite in Chicago

2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking

This 100% private apartment in the lower level is just minutes away from O'Hare, Rosemont, Allstate Arena, I90, & the CTA. About 30 minutes from downtown or Wrigley Field. This two-bedroom private apartment in a newly built single-family home has plenty of space in an open-concept living room, kitchen, & dining room for big families. You will have a separate private entrance, fast wi-fi, full kitchen, & laundry. You will have 1 queen bed, 4 twin beds, & 1 air bed. There is free street parking.

Apartment in Norwood Park

The living room features a cozy seating arrangement with two dark chairs and a sofa, set around a central table. A decorative rug adds warmth to the wooden flooring. Natural light floods in through large windows, while a ceiling fan enhances airflow in the space.

4.96 out of 5 average rating, 101 reviews

Spacious and Cozy 3BR Apt Near ORD / Metra

Welcome to our charming and cozy apartment. This apartment is designed to be your home away from home in Chicago. From the moment you step inside you will be captivated by the tasteful decor and attention to detail. The apartment is located in a great neighborhood close to public transit and highways. Also, you will find plenty of restaurants, cafes, shop, and entertainment options nearby. Our apartment offers a comfortable and inviting atmosphere perfect for your next vacation or business trip.

4.87 out of 5 average rating, 707 reviews

A spacious living area is highlighted by a black sofa facing a light-colored coffee table. A vibrant area rug adds color underfoot. The walls are adorned with colorful vinyl records and framed artwork, while original woodwork details frame the open layout leading to the dining area.

Apartment in Oak Park

Rockin' 2Bed steps to shops/food/train

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

4.77 out of 5 average rating, 553 reviews

A modern kitchen area features a wooden accent bar with four metal stools. Stainless steel appliances, including a refrigerator and stove, are visible. A wall clock adds a functional element to the open concept design, with neutral tones enhancing the spacious ambiance.

Apartment in Park Ridge

Modern Garden apartment (WHOLE UNIT)

Freshly Remodeled , Lower Level garden apartment one bedroom one bath. Older building with wooden floors. If hearing people upstairs walking can bother you , do NOT book it please .Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10min to outlets Absolutely NO parties, NO gathering Quiet hours 10 pm till 6.00 am

Apartment in Jefferson Park

A living area features a dark leather sofa with red accent pillows, paired with two leather chairs. A wooden coffee table sits centrally, surrounded by warm-toned lighting. The space opens to a kitchenette with a retro red refrigerator and tall bar seating, creating an inviting atmosphere.

4.86 out of 5 average rating, 249 reviews

Cozy & Comfy 1bd In Historic Portage Park Bungalow

Make yourself at home in my comfortable Portage Park one bedroom garden apartment. This spacious condo is bright and airy with warm furnishings, a kitchenette with an island, private bedroom with a full bed and a modern bathroom with a glass walk-in shower. Portage Park is Chicago’s largest Polish neighborhood and is home to vintage charm, heaps of history and classic Chicago-style bungalows. The National Veterans Art Museum is a poignant must-see while you’re here with its combat-era art.

4.97 out of 5 average rating, 148 reviews

The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.

Apartment in Dunning

Belmont Pleasures - hot tub / arcade gaming room

Welcome home! If you’re looking for a unique experience to enjoy with your friends and family come have some fun in this beautiful luxury home, located in belmont-cragin neighborhood Chicago IL 60634 The spacious house includes 3 bedrooms, 4 full bunkbeds , 2 queen beds , 2 sofa queen beds , 2 & 1/2 bathrooms . Whether you’re looking to book for a birthday, bachelor/bachelorette gathering, or trip with family and friends, this place has something for everyone.

Guest suite in Portage Park

A brick bungalow features a welcoming front porch adorned with a US flag. The porch includes a railing and seating area, while flower pots add greenery. Stairs lead up to the front door, which is detailed with a decorative screen.

4.95 out of 5 average rating, 178 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Private entrance apartment on the 2nd floor of this historic bungalow. Free street parking! Medicinal & recreational smokers permitted... outdoor ONLY. This comfortably cozy quiet get-away is nestled in NW Portage Park in a family neighborhood. Dog and kids park nearby. Fenced yard for Fido. Backyard patio w/ BBQ grill. High-speed internet. Front porch swing Easy access to buses & Jefferson Park Transit train station to Downtown & Museum Campus NO PARTIES

Apartment in Lincoln Square

A cozy living area features two dark leather sofas, a marble-topped coffee table, and a flat-screen television. Natural light enters through a window with blinds, while a warm brick wall adds character. A decorative console table is positioned along the side of the room.

4.91 out of 5 average rating, 274 reviews

Newly Rehabbed! 2br with Vintage Charm

Our 2 bed garden apartment in Ravenswood will be the ideal home base for your stay! Located in one of Chicago's vibrant Northside neighborhoods, you’ll experience local charm outside your door. The home has space for 5 and a newly renovated kitchen, though you may not have time to cook with many family-owned restaurants within walking distance! The Montrose Brown Line is only 3 blocks away, taking you downtown in 30 minutes and Lakeview/Lincoln Park in even less.

Apartment in Jefferson Park

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.

4.93 out of 5 average rating, 117 reviews

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!

4.78 out of 5 average rating, 283 reviews

A living area features a leather sofa and two upholstered chairs, arranged around a glass coffee table. A brick accent wall provides character, while a large television sits atop a wooden console. Artworks adorn the walls, accompanied by natural light from the windows.

Condo in Logan Square

Logan Square Beauty with 2 Bedrooms W/parking

Our two-bedroom condo is beautifully appointed and has vintage charm everywhere you look. You'll have access to a shared backyard, and all of the amenities of home - while being a 10 minute walk from some of the hottest bars and restaurants in Chicago. One garage parking spot is available during your stay. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea!

4.91 out of 5 average rating, 345 reviews

A cozy living area showcases a mix of modern and rustic design elements. Exposed brick walls enhance the character of the space, while natural light filters through the windows. A comfortable sofa and a wooden coffee table are positioned atop a geometric-patterned rug.

Apartment in Bucktown

Bright & Lofty Bucktown 1br

My top-floor apartment in Bucktown is the perfect space for your trip to Chicago! It's a stylish, modern rehab in a classic Chicago building, so you really see the best of what the city has to offer! It's just off beautiful Holstein Park, and easy walking distance to 2 Blue Line stops - so you can get to the Loop in under a half hour! And plenty of Logan Square favorites along Milwaukee are a 15 minute walk away - book today!

Apartment in Norwood Park

A bright living area features a brown leather sofa with two decorative pillows, accompanied by a teal coffee table and a woven rug. Sunlight streams through two windows, highlighting a rocking chair and indoor plants, creating a relaxed and inviting ambiance.

4.93 out of 5 average rating, 272 reviews

Charming Chicago Apartment | Near O’Hare+Blue Line

Bright, private upstairs apartment in a quiet NW Chicago neighborhood—just 10 minutes from O’Hare and close to the Blue Line. Enjoy a comfy king bed, full kitchen, fast WiFi, and smart TV. Walking distance to shops, restaurants, and Harlem-Irving Plaza. Free street parking, private entrance, and self check-in make your stay easy and relaxed. Ideal for solo travelers, couples, or remote work.

Popular amenities for Norwood Park family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guesthouse in Lincoln Square

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.

4.89 out of 5 average rating, 340 reviews

Private Coach house near Lincoln Square!

4.95 out of 5 average rating, 156 reviews

An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.

Home in Bridgeport

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

4.96 out of 5 average rating, 280 reviews

A modern kitchen features a large stainless steel island with seating for three. Black cabinetry offers ample storage space, complemented by open shelves displaying various kitchen items. Pendant lights hang above, illuminating a stylish workspace adorned with greenery, while industrial elements add character.

Loft in Wicker Park

Tea Studio in Wicker Park Spring Factory

4.96 out of 5 average rating, 165 reviews

An outdoor patio is showcased, featuring a rectangular fire table surrounded by four cushioned chairs. The wooden decking contrasts with the subdued colors of the furniture. A partial cover is draped over one corner, providing shade from the sun.

Condo in West Town

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Apartment in East Rogers Park

An open-concept living and dining area is showcased with a gray sectional sofa and a wooden coffee table. A modern ceiling fan hangs above, and natural light fills the space. A dining table with six chairs is positioned nearby, adjacent to a sleek kitchen.

4.85 out of 5 average rating, 101 reviews

Spacious Beautiful Condo

4.86 out of 5 average rating, 173 reviews

A spacious spa room features a modern two-person jacuzzi, surrounded by elegant marble walls. The jacuzzi is designed with a clear accent panel, and amenities such as towels are neatly arranged nearby, promoting a calming and relaxing environment.

Home in Whiting

The Spa of Downtown Whiting

4.92 out of 5 average rating, 101 reviews

The living area features an expansive sectional sofa arranged around a coffee table, complemented by a textured rug. Natural light floods in through large windows, illuminating the open space that connects to a modern kitchen with sleek cabinetry and an atmospheric dining area.

Home in Bridgeport

Luxurious 7-Bedroom Retreat in Chicago

Apartment in Humboldt Park

An open and spacious living area features a white sectional sofa and unique cow print coffee table. The dining space is equipped with round chairs, and a modern kitchen is visible in the background. Light streams through frosted glass block windows, enhancing the airy atmosphere.

4.86 out of 5 average rating, 491 reviews

Checkerboard Studio, Private Outdoor Hot Tub, Yard

Family- and pet-friendly home rentals

Apartment in Lincoln Square

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.

4.95 out of 5 average rating, 409 reviews

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

4.96 out of 5 average rating, 139 reviews

The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.

Condo in Avondale

Lovely top floor 2BR/2BA, steps from everything!

4.97 out of 5 average rating, 453 reviews

A bright living area is showcased with large windows allowing natural light. Red and orange artwork adorns the walls, while a gray ottoman centers the room. Seating consists of a gray sofa and an armchair with a geometric pattern, accompanied by decorative lamps on either side.

Condo in Lincoln Square

Lincoln Square Gem!

4.82 out of 5 average rating, 121 reviews

Apartment in Avondale

Heart of Logan Sleeps 5 - Games - Great Area

4.88 out of 5 average rating, 329 reviews

A spacious living area features a modern sectional sofa in neutral tones. A sleek television is mounted on the wall opposite a minimalist coffee table. The adjoining dining area, visible through an archway, includes a round table with four chairs.

Apartment in Forest Park

Home in Forest Park Upstairs.

4.84 out of 5 average rating, 171 reviews

A spacious living area is highlighted by a large sectional sofa positioned around a light area rug. Natural light filters through the floor-to-ceiling windows, while a sleek TV is mounted on the wall. Decorative plants and modern furnishings add to the inviting atmosphere.

Condo in Chicago

Marvelous Condo w/ Pri Prkng Cls to Transit &Beach

4.97 out of 5 average rating, 854 reviews

A spacious living room features three large windows allowing natural light to fill the space. Comfortable seating includes a leather couch and an armchair. A television is mounted on the wall, and a decorative area rug lies beneath a wooden table set for dining.

Condo in Noble Square

Great location. Free parking.

4.92 out of 5 average rating, 127 reviews

The open-concept living space features natural light streaming through skylights and a mix of wooden accents and plants. A comfortable green sofa and a chair are positioned along the walls, while a sliding barn door leads to the adjacent bedroom area.

Apartment in Avondale

Avondale Cozy 1 Bedroom Attic Apartment 4th FL

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 148 reviews

Home in Highland Park

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Apartment in Chicago Loop

A bright living area features large windows that offer city views, enhanced by natural light. Comfortable gray seating is arranged on a patterned rug, complemented by modern decor and greenery. A flat-screen TV is mounted on the wall, alongside a stylish coffee table.

4.83 out of 5 average rating, 293 reviews

Spectacular 2BR Penthouse in the Loop | Roof Deck

4.92 out of 5 average rating, 135 reviews

A dining area is presented with a sleek table surrounded by four black chairs. A grey sectional sofa is positioned nearby, complemented by a modern floor lamp. Large windows provide natural light, and a vibrant cityscape photo adorns the wall.

Condo in Evanston

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

4.81 out of 5 average rating, 52 reviews

An indoor swimming pool stretches along a glass wall, offering views of the outdoors. The space is highlighted by modern lounge chairs and sleek tile flooring. Natural light floods the area, enhancing the serene ambiance created by the tranquil water features.

Apartment in Grant Park

Sentral 2 Bedroom Apt in South Loop Chicago

Apartment in Fulton Market

4.85 out of 5 average rating, 130 reviews

33rd-Floor Penthouse with Breathtaking Views

4.9 out of 5 average rating, 561 reviews

A cozy bedroom features a spacious bed dressed in bold black and white striped bedding. A decorative red pillow adds a pop of color. A framed artwork of a rabbit is displayed above the bed, complemented by bedside tables with a lamp and a small potted plant.

Apartment in Uptown

Whole Flat in Private Club. Walk to L, Dining & Shows

4.9 out of 5 average rating, 115 reviews

An outdoor pool is surrounded by lounge chairs in various colors, creating a bright and inviting atmosphere. Tall buildings are visible in the background, and the pool reflects the clear blue sky overhead.

Apartment in South Loop

The Executive's Escape (2BD / 2BA)