Pet-friendly holiday rentals in Northwest Side

Lovely, bright, 3-bedroom Avondale flat. Private.

3 bedroom apartment perfect for families or groups of 3-5 people. Transportation is accessible with many CTA bus stops nearby, the Kennedy expressway only minutes away, and two Blue line stations less than a 15 minutes walk. The newly redecorated apartment is located on a quiet street in the up-and-coming Avondale neighborhood with free street parking (parking permit will be provided). Only a few minutes away from Logan Square, amazing restaurants, nightlife, and entertainment are easy to find.

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

Paradise on the Boulevard!

Amazing 2 bedroom garden apartment, located in the heart of the highly desirable Logan Square. This luxurious space with heated polished concrete floors & spa inspired bathroom is situated on the Historic Logan Boulevard, just steps from CTA Blue Line. Fabulous restaurants and coffee shops across the street. The apartment has a private entrance & access to a fabulous shared backyard space. The owner's treehouse deck can be reserved by request. Peace, convenience & excitement are right here.

Irving Park/Avondale updated vintage top unit

Experience a true Chicago neighborhood in a classic vintage (but updated) two-flat apartment just 10 minutes from Wrigley Field, 4 minutes from I-90/94 and a 15-minute walk or short bus ride to the blue line. Central air/heat and free street parking. I'm a former Super Host and capital P Perfectionist, but decided to list the space before it's perfect to help cover the cost of future renovations. As long as you don't mind not having a brand-new bath/kitchen and fresh paint, you'll love it!

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.

Sunny Logan Square Artists' home

2nd floor classic Chicago 2flat with lots of light. 3 bedrooms available, with 2 additional sofabeds. Great if you and family/group of friends are in town for an event and want to stay together. Grocery store 1.5 blocks away. Quiet street. Parking is decent. New bath has all marble walls, extra long/deep tub and rain shower. 1 mile walk to the Logan Square CTA Blue Line and Logan Square brunch/night-life. 5 min walk to Metra. Walk to 606 trail. Chicago Registration Number: R24000117459

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

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

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

ITALIAN garden apt/kids friendly/great location!!

Ciao! My name is Viviana I am Italian and I live with my family, my husband and 2 girls, I hope you will enjoy our cozy guest garden APARTMENT within our home, featuring a queen size bed, a sofa bed good for a small person or a toddler, 2 twin foldable beds, TV where you can enjoy cable channels, movies and other amenities like, laundry, little kitchenette with a MINI refrigerator, microwave, snacks and hot plates if you like to cook something. Arrivederci!

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.

Eddy Street Upstairs Apartment

Make yourself at home in our comfy, cozy upstairs apartment! Located in the Portage Park neighborhood of Chicago, we are close to great food, parks, and fun outings! You can get to O'Hare Airport in less than 20 minutes, depending on traffic. And we're about a 25 minute drive to downtown, or about 45 minutes via public transit. We have free street parking on our block!

Renovated Loft on Milwaukee Ave

Bring the whole family to this modern loft with lots of room for fun! Located in north Logan Square right above the main strip on Milwaukee Ave and its vibrant restaurant scene. Only 0.4 miles from the Logan Square Blue line stop, which runs 24 hours to O'Hare airport and downtown Chicago. Free street parking and parking passes to park on permit parking streets.