Holiday rentals in North Side

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.

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

The Chicago River House – GIANT wall projector!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

Walkable Logan! 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

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.

Luxury home + Huge Yard in Avondale Logan Square

Welcome to Emerald Oasis— a stylish 2-bed, 1-bath retreat on a rare double lot in Avondale, voted the 5th coolest neighborhood in the world. Nestled between downtown Chicago and O’Hare International Airport, this eclectic home blends vintage charm with modern comfort—perfect for couples, families, or friends. Unwind by the fire pit in the fully fenced yard after a day exploring the city. Whether for work or play, Emerald Oasis offers a relaxing, photo-worthy stay to make lasting memories.

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Private Jefferson Park Home

Welcome to Chicago's very own Jefferson Park! Just-renovated two bedrooms, one bathroom unit with private access -2 Blocks to Metra - 10 min to O'Hare, Rosemont & Allstate Arena - 20 min to Downtown/Wrigley Field - Free High-Speed Wifi & Smart TV - Ample/Free Street Parking - Access to Interstate 90 - Walking Distance to Restaurants & Coffee - Brand New Stove, Refrigerator, and All-in-One Washer/Dryer - Bedrooms with Brand New Ceiling Fans - Convenient Keyless Entry on YOUR Schedule!

SW Evanston Private, Stylish, Spacious Suite

Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

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!

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.

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!