Family-friendly vacation rentals in West Loop

4.86 out of 5 average rating, 477 reviews

An ivy-covered brick facade presents a charming entrance. A black door with decorative window details is centered, flanked by a small garden featuring well-maintained greenery. A gravel pathway leads to the entrance, showcasing the unique character of the historic coach house.

Guesthouse in West Loop

Pro Cleaned & Isolated West Loop Coach House

Mimi & Paul's historic ivy-covered two-level coach house has a private entrance and an airy queen bedroom. The renovated kitchen is outfitted with European-sized appliances, though you'll probably have no time to cook since you're surrounded by the best restaurants Chicago has to offer. All of the essentials are provided to make your stay easy and comfortable...paper products, soaps, shampoo/conditioner/body wash, towels, linens and even coffee/tea! (See layout in "Other Details To Note" below)

4.9 out of 5 average rating, 102 reviews

The living room features a spacious, light-colored sectional sofa adorned with orange and black cushions. A coffee table sits in front, accompanied by a cozy pouf on a patterned rug. A mounted TV is visible, along with large windows allowing natural light to brighten the room.

Condo in West Town

Welcome to the Chi! Close to Downtown

Welcome to this contemporary, urban retreat in the bustling heart of River West. This entire unit is thoughtfully designed with modern convenience, catering to those seeking stylish and comfortable accommodation. This trendy unit is in a prime location, just a short walk to the Blue Line and minutes away from 90/94. With an array of restaurants, grocery markets, coffee shops, and stores within walking distance, you'll have the best of Chicago at your doorstep. 5 minute drive to United Center.

4.95 out of 5 average rating, 140 reviews

A bright living area features a comfortable gray sofa with decorative pillows, a round coffee table, and large windows overlooking a private outdoor space. Light wood flooring complements the modern kitchen area, which includes sleek bar stools and stainless steel appliances.

Apartment in West Loop

Perfect Spot & Spacious 2BR+2BA | Mapletree Suites

Welcome to Mapletree Suites! Our stylish, clean, and contemporary 2 bed+2 bath suites are located in a boutique building in Chicago’s booming West Loop neighborhood. Keyless entry, blazing fast WiFi, bright white linens, in-unit laundry, 10ft ceilings, balconies, Italian cafe, host on-site, plus much more! Steps from Target store, parks/athletic field, CTA, and close to United Center, world-class restaurants, loop/lakefront, Med District, UIC, corporate offices and highway network. Book today!

4.92 out of 5 average rating, 103 reviews

A spacious living area features a comfortable dark sofa with decorative red and blue pillows. A soft area rug lies beneath a wooden coffee table. Natural light fills the room from large windows, illuminating the cozy sleeping area with a neat bed dressed in light linens.

Guest suite in West Town

Renovated basement studio w/ independent entrance

Make this newly renovated studio located near the heart of Chicago your home away from home. Set at the vibrant Noble Square/Eckhart park neighborhood within West Town where you are walking distance to restaurants, bars, park and public transportation that takes you straight to downtown. Luxe & comfort throughout- stocked kitchen, new king size memory foam bed and gel-infused pillows, queen bed sofa & a work area. Great for city explorers, couples with or without kids and business travelers.

Apartment in Little Italy

The living room features a stone accent wall with a mounted flat-screen TV centered above a fireplace. Dark blue sofas are arranged around a light-colored ottoman, while a patterned area rug extends across the dark wood floor. Natural light enters through the nearby window.

4.98 out of 5 average rating, 273 reviews

Spacious 2BR on Quiet St - Free Park/Late Checkout

2 bedroom, 1 bathroom apartment, located just off Taylor Street in the heart Little Italy! Safe and lively neighborhood with many diverse restaurants, cafes, bakeries, parks, etc. all just a short walk from the apartment! Nearby West Loop also packed with trendy shops and amazing dining spots. Flat screen TV in every room, In-unit laundry, patio space, coffee/tea provided. 1pm check out 👍 Easily accessible to United Center, Soldier Field and downtown. Located on Chicago Marathon route.

4.95 out of 5 average rating, 118 reviews

A spacious bed with a dark wood frame is positioned against a teal wall, flanked by matching nightstands and elegant lamps. A round mirror above the bed reflects soft light, while a textured blanket rests at the foot. Rich curtains frame the windows, adding depth to the room.

Apartment in West Loop

Fulton House #1 - Studio Only (Nightly)

Unique & stylishly designed by Chicago's own Outline Interiors, this highly sought after location is for those that want to stay on a calm side street around the corner from city's best, award-winning restaurants and trendiest shopping. The fully-serviced studio has the business-travel amenities you want: ultra speed wifi, work station, top tier dining options within steps, Nespresso coffee maker, bottled water and more. Paid parking next door $20/day, subject to avail - inquire in advance.

4.96 out of 5 average rating, 140 reviews

The living area features a large gray sofa, a stylish armchair, and a modern media console with a television. Natural light filters through two large windows, providing a view of the surroundings. A small plant and decorative rug add subtle touches to the space.

Apartment in West Town

Millennium park 10 min Free P-Spot&Balcony Sleep 8

FREE & SECURE ONE IN-DOOR PARKING SPOT!!! You would enjoy staying in the spacious 1800 sq ft with 10 ft high ceilings. 2 bedroom/2 bathroom apartment with ZERO STAIRS to get inside! It is an excellent solution for elder people and families with kids or maybe just a group of friends coming to have fun at the UNITED CENTER sports event or tourists as well as business folks or doctors to attend McCormick Place conferences. Bring the whole family to this great place with lots of room for fun.

4.98 out of 5 average rating, 368 reviews

A spacious living room features a decorative fireplace and large bay windows that allow natural light to fill the space. Comfortable seating options include a light-colored armchair and couch, complemented by a glass coffee table and a colorful area rug.

Home in West Loop

Cozy garden apartment historic Jackson Bvld.

Just a short walk to the United Center our cozy 1 bdrm garden apt is located on Historic Jackson Blvd's tree lined st. Stop back & warm up by the fireplace before heading out to near by shopping & restaurants. Less than an hour from Midway or O'Hare. Walking distance to Randolph St. Restaurant Row, Little Italy, Greek Town, Union Pk, Fulton Warehouse Dist, Rush Hospital and UIC. A quick train/bus to The Loop, Theater Dist, Mag Mile, Wicker Pk. Free, convenient street pkg.

Apartment in Fulton River District

The kitchen area features a modern design with wooden cabinetry and a sleek countertop. Four black bar stools are positioned at a counter, which faces an abundance of natural light from a window. The kitchen is equipped with new appliances and organized shelves for easy access.

4.97 out of 5 average rating, 438 reviews

Peaceful River West, free parking

This Apt can be rented separately or together with Comfy River West Apt. https://abnb.me/aoJ0F64vDY This one on the the 2nd floor and one directly above on the 3rd floor. Together they will sleep 8 guest. This beautiful 2BR, 1 BA has all new furniture, all new appliances, counter tops, vanity, mirrors. Free parking in a gated lot, Level 2 EV charging available for electric cars. Shared patio/gardens and grill. Fully stocked kitchen, private washer & dryer.

4.74 out of 5 average rating, 170 reviews

A modern studio apartment features a spacious bed with white pillows and a navy blue blanket. A sleek kitchen with stainless steel appliances and wooden cabinetry is visible in the background. A black sofa and a round white dining table complete the living area, with natural light coming through a window.

Condo in River West

Cabin 104 at 747 Lofts

This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away!

4.95 out of 5 average rating, 137 reviews

An open kitchen and dining area features exposed wooden beams and stylish light fixtures. A modern dining table with black chairs provides seating, while a lounge chair is positioned nearby. Decorative plants and art add warmth to the contemporary space.

Condo in Wicker Park

Modern Izakaya Studio in Wicker Park

Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

Apartment in Fulton Market

The living area features an open design with large windows providing ample natural light. Two comfortable chairs and a sofa are arranged around a coffee table. Exposed brick walls and wooden beams create a warm atmosphere, complemented by indoor plants and a stylish lamp.

4.84 out of 5 average rating, 252 reviews

Beautiful Luxury Loft in Fulton Market, Sleeps 12

Newly renovated designer 2,500 square foot brick-and-timber loft with 15 foot ceilings located in the heart of the vibrant West Loop neighborhood. This huge 2 bedroom / 2 bath apartment is perfect for groups looking for a stylish city escape surrounded by Chicago's best dining and nightlife. The central location is an ideal base for everything you want to see in Chicago!

Popular amenities for West Loop family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.79 out of 5 average rating, 132 reviews

Apartment in River North

Level ◆ Brand New Luxe One Bedroom

Guesthouse in Bownmanville

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, 355 reviews

Private Coach house near Lincoln Square!

4.85 out of 5 average rating, 330 reviews

A spacious living area features a blend of warm wall colors and modern decor. Comfortable seating includes a light-colored sofa and a wooden chair. A fireplace is highlighted on one wall, accompanied by a ceiling fan and natural light from large windows.

Home in River West

Lux Urban 3BR/3BA Duplex + Parking!

4.95 out of 5 average rating, 157 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

4.87 out of 5 average rating, 77 reviews

An indoor pool area is featured, highlighting a clean, rectangular swimming pool surrounded by large windows. Lounge chairs are positioned along one side, offering a place to relax. The space is bright with neutral-colored walls and a minimalist design.

Apartment in The Loop

The Aerial Oasis (Indoor Pool • Fitness Center)

4.96 out of 5 average rating, 169 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

4.93 out of 5 average rating, 161 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

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, 510 reviews

Checkerboard Studio, Private Outdoor Hot Tub, Yard

Family- and pet-friendly home rentals

Apartment in Noble Square

A modern living area is shown featuring a light-colored sectional sofa and a wall-mounted television. Natural light enters through large windows, and a small indoor plant adds a touch of greenery. A low coffee table sits in front of the seating area, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 114 reviews

Wicker Park Walk-Up Condo

Apartment in Roscoe Village

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

4.95 out of 5 average rating, 237 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

4.94 out of 5 average rating, 101 reviews

A bright living area features a deep green accent wall and polished concrete floors. A plush dark sofa with decorative pillows is positioned facing a television on a wooden stand. A window offers a view of an outdoor space, enhancing the natural light in the room.

Apartment in The Loop

Loop Loft-Subway & Art Institute

4.9 out of 5 average rating, 136 reviews

An open living space is visible, featuring a cozy seating area with a brown couch and two green armchairs. A large area rug adds warmth beneath the coffee table. A kitchenette area with wooden counter space and modern appliances is present, while bookshelves display various books and decor.

Apartment in West Town

Garden on Warren

Apartment in Magnificent Mile

A modern living room features a warm fireplace with elegant stone detailing. Comfortable seating is provided by a plush sofa alongside a stylish armchair. Natural light enters through multiple windows adorned with blinds. Decorative elements include a wooden coffee table and contemporary wall art.

4.98 out of 5 average rating, 130 reviews

Chic 2BR Gem with Fireplace

Guest suite in Near Southside

A contemporary kitchen area features wooden cabinetry and modern appliances, including a coffee maker and microwave. A small island with two stools offers space for dining. The tiled floor extends into a hallway lined with framed artworks, while a cozy seating area is adorned with patterned cushions.

4.76 out of 5 average rating, 198 reviews

Mckelvin Garden suite

4.97 out of 5 average rating, 164 reviews

A two-story white house is featured, displaying large windows that allow natural light to brighten the façade. The entrance is marked by a covered porch with steps leading up, while planters are placed on either side of the door against a tree-dappled background.

Home in Lincoln Park

Charming 3-BED in Lincoln Park/ Old Town & Parking

4.91 out of 5 average rating, 302 reviews

A spacious living area features large windows allowing abundant natural light. Exposed Chicago brick adds character to the space, while hardwood floors extend throughout. A comfortable sectional sofa, a chic armchair, and a tasteful area rug create a welcoming atmosphere. A television and decorative furnishings are also visible.

Apartment in West Town

✨Spacious Centrally Located West Loop Loft✨

Family-friendly home rentals with a pool

Apartment in Printer's Row

5 out of 5 average rating, 12 reviews

Upscale High-Rise Apt · Rooftop Pool + Views

Apartment in Printer's Row

A rooftop pool area is showcased, featuring clean lines and modern architecture. The pool is rectangular and bordered by sleek railings. Surrounding urban buildings are visible against a clear blue sky, highlighting the vibrant city atmosphere.

4.83 out of 5 average rating, 59 reviews

South Loop | Rooftop With In & Out Parking | 2

4.67 out of 5 average rating, 343 reviews

A spacious indoor garden lounge features abundant natural light streaming through large windows. Modern white furniture is arranged around a central coffee table, surrounded by lush greenery and decorative plants. The airy atmosphere is enhanced by hanging light fixtures, creating a serene and inviting space.

Apartment in Grant Park

Sentral Premium 2BR Apt South Loop Chicago

4.92 out of 5 average rating, 137 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

Apartment in Fulton Market

A bright and airy living area is filled with natural light from floor-to-ceiling windows, offering expansive city views. A plush sectional sofa is positioned on a soft area rug. Potted plants and a console with a television add to the inviting ambiance.

4.97 out of 5 average rating, 34 reviews

Skyline Oasis: City & Lake Views

4.9 out of 5 average rating, 573 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

Apartment in Printer's Row

A modern living area features a light-colored sofa with dark throw pillows, complemented by a sleek coffee table. Two abstract artworks adorn the wall above the couch. A plant adds a touch of greenery, while a large window allows natural light to fill the space.

4.86 out of 5 average rating, 36 reviews

Downtown 3BD 3BA Condo|Parking, Pool, Gym, Rooftop