Apartment holiday rentals in North Side

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.

Value · Location · Checkout

Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!

Located in the heart of Wicker Park, just a 5 min walk to the Damen blue line stop. This phenomenal location allows you to access EVERYTHING Chicago has to offer without having to rent a car. Experience the best of Chicago, all within a short walk from your stay. World class bars, restaurants, and shopping all within walking distance. Want to explore downtown or catch a Cubs game at Wrigley? Hop on the "L" train and use the CTA to go anywhere in the city. This cozy garden apartment has it all.

Family · Value · Laundry

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.

Family · Location · Walkability

King Sleep Number Bed – No Cleaning Fee

Unwind in luxury on a king-sized Sleep Number bed, refresh in a sleek marbled bathroom, and channel your inner chef in a farmhouse-inspired kitchen with many amenities. This bright and airy space is the perfect retreat after a day of exploring. Located near CTA bus stops, getting around the city is a breeze. Whether you're here for business or pleasure, our home offers the ideal mix of comfort, style, and convenience. Book your stay today and experience Chicago in elevated comfort!

Location · Family · Layout

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!

Family · Location · Comfort

Balcony • 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.

Value · Family · TV

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

Value · Location · Decor

LIVN West Loop Chicago Queen Studio Apartment

Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.

Value · Location · Laundry

1BR Bright Bucktown Loft - Great Location!

Welcome to your ideal Chicago getaway! Located in vibrant Bucktown, this top-floor, modern rehab combines contemporary style with classic Chicago charm. Sitting right off beautiful Holstein Park, you are just a short walk from two Blue Line stops—getting you to the Loop in under 30 minutes! Plus, you'll be within a 15-minute stroll of Logan Square’s top restaurants, nightlife, and shops along Milwaukee Avenue.

Family · Value · Air conditioning

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.

Location · Family · Sleep quality

Entire 1st Floor Apt near O'Hare/ORD & Blue Line

You’ll love my place because of the privacy, comfort, first-floor convenient access (no stairs), no clutter, the ambiance, the neighborhood, free on-street parking, and your host (conveniently living in a separate apartment on the second floor). My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets).

Family · Value · Breakfast

Relax & Walk to Wrigley Field from this Comfy Home

Stay at this two-bedroom, two-bathroom garden apartment on a beautiful tree-lined street in Chicago's North Center neighborhood. Wrigley Field is just over a mile away and Lake Michigan is two miles east. The brick building is also walking distance to restaurants, bars, a brewery, Trader Joe's grocery, and public transportation.

Family · Value · Parking