Holiday rentals with outdoor seating in North Side

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, 103 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.

Guest favourite

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.

4.94 out of 5 average rating, 459 reviews

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

An airy studio bedroom features a spacious bed with white linens and decorative pillows. Large windows allow natural light to fill the room, showcasing a cozy sitting area with a small table and chair. Framed botanical artwork adorns the walls, contributing to a calming ambiance.

4.99 out of 5 average rating, 401 reviews

Private Lincoln Square one bed+bath studio apt.

Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

4.97 out of 5 average rating, 473 reviews

King Bed, Huge Spa Shower, Dining Destination

This home was designed with love! Inspired by our favorite boutique hotels - nestled on a tree-lined street in Logan Square, a locals-only destination for brunch, coffee, craft beer and cocktails. Relax in the massive custom steam shower or catch up on HBO on the 50” WiFi TV. Luxe details throughout -premium espresso, memory foam beds and upgraded Italian linens, lots of outlets, and a fully-equipped kitchen. Easy parking, a rarity in the city. Central location- Quick walk to Blue Line Train

The living area features a comfortable blue sofa adorned with decorative cushions, complemented by a patterned rug. A soft pink armchair and a small round coffee table are present. A vibrant floral painting hangs on the wall, and natural light enters through the window covered by light curtains.

4.96 out of 5 average rating, 392 reviews

Gorgeous, cozy 1-bedroom Suite in Andersonville

Our place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, location, complete privacy and NO cleaning fee. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.

A spacious living area features a plush blue sofa facing a flat-screen TV on a modern table. A wood dining table with chairs is positioned in the corner. Neutral walls and tile flooring create a bright and welcoming atmosphere.

4.97 out of 5 average rating, 185 reviews

Gorgeous Studio 15 Minutes From Ohare!

Private, cozy and spacious studio apartment. This wonderful apartment is clean and ready to be your home away from home in Chicago! Full kitchen and bath! Spacious Backyard! Free Parking! On a beautiful treelined street in the Dunning neighborhood. Great for couples & business travelers! Close to great restaurants and parks, Rosemont Convention Center (10 minutes), O’ Hare Aiport (15 minutes), Downtown (35-45minutes). *Travel times are non rush hour and can increase depending on time/events*

Guest favourite

A spacious bed with patterned bedding rests against a geometric accent wall painted in dark blue and vibrant yellow. Two nightstands with lamps are positioned on either side, contributing to the cozy and modern aesthetic of the room.

Flat in Maywood

4.95 out of 5 average rating, 182 reviews

Cozy guest studio, great for couples!

This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

Superhost

A modern galley kitchen features green cabinetry and white countertops. A decorative backsplash with a floral pattern complements the design. Appliances include a gas stove, dishwasher, and coffee maker, while ample shelving showcases houseplants and decorative items.

4.86 out of 5 average rating, 180 reviews

Funky & newly remodeled 1 bed in Hip Logan Square

Recently remodeled 1 bedroom garden apartment with a fun aesthetic in hip Logan Square. Walking distance to top bars, restaurants and coffee shops such as Sugarmoon, Park & Field, Best Intentions, Lou Malnatis, Damn Fine Coffee Bar and many more. Blocks from the 606 Trail, 90/94 & public transportation. Lovely shared front yard landscaped with florals + garden beds. We will pass along a welcome guide with a list of all our favorite places in the neighborhood!

Guest favourite

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, 434 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.

A lounge area features a curvy orange sofa, complemented by a black circular coffee table resting on a textured cream rug. Natural light filters through large windows, illuminating framed wall art with subtle hues. Minimalist decor creates a cozy and inviting atmosphere.

4.94 out of 5 average rating, 158 reviews

Logan Square Garden Suite

Creative and quiet light-filled garden unit with lots of books, accompanied by comfortable lounge furniture and touches of nature for cozying up and relaxing after long travel or late nights. This is a perfect space for solo travelers or couples. This is also a great space if you are traveling with a small child or infant. The place is set up much like a hotel room in that it does not have a kitchen but we do provide a mini fridge and Nespresso machine.

4.96 out of 5 average rating, 113 reviews

A modern kitchen and dining area features sleek cabinetry and a large window allowing natural light. A glass dining table with blue chairs is positioned centrally, adjacent to stainless steel appliances and counter space. Light hardwood flooring enhances the spacious look of the room.

Home in Chicago

Northside Chicago Getaway

This home is a classic Chicago bungalow that has been recently updated. There are some special features including whole home audio, a 75" TV with 9.1 Dolby atmosphere surround sound, a 3-person sauna, complete kitchen, fire pit out back and private parking for 2 cars. The Home is located in the Mayfair Park area of Chicago and offers a taste of the City life but also has a little space to breathe. Hope you enjoy it as much as I have over the years!

A bright living room is illuminated by natural light from large windows. A white sofa is paired with two orange chairs, complemented by vibrant cushions. A coffee table with a striped design sits centrally, surrounded by decorative plants and artwork on the walls.