Holiday houses in Near North Side

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Family · Value · Nearby

Luxury Penthouse Loft w/Terrace 504 | River North

BRAND NEWPENTHOUSE DUPLEX LOFT IN THE HEART OF RIVER NORTH WITH PRIVATE TERRACE! Enjoy your luxury two-story designer styled apartment located in Chicago's center of nightlife, restaurants, and shopping. In a completely renovated luxury building, your 2 bedroom/1.5 bathroom duplex loft apartment with spectacular outdoor terrace and two living rooms offers a great design, nice finishes, and great large layout with large living space and bedrooms, perfect for families traveling to Chicago, pro

Location · Family · Comfort

Kasa Lake Shore Chicago | Two Bedroom King & Queen

Kasa Lake Shore Chicago offers spacious, furnished apartments for short and extended stays, steps from Lake Michigan, Navy Pier, and the Magnificent Mile. Each tech-enabled unit has a full kitchen, in-unit laundry, and access to co-working areas, offering more space than a hotel for business and leisure travelers. Check-in starts at 4pm and can be done contactless from your phone, or in person at our front desk, open daily from 11am to 730pm. Text us anytime for Virtual Front Desk support.

Family · Location · Air conditioning

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.

Location · Value · Nearby

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 · Family · Laundry

Gold Coast Chicago Condo | Prime Downtown Location

Enjoy a stay in Chicago’s sought-after Gold Coast in this inviting 2-bedroom, 1-bath condo. Situated on the third floor, the unit offers a bright, comfortable layout with the convenience of an in-unit washer and dryer. Paid street parking is available nearby, and you’ll be centrally located to Chicago’s biggest attractions—minutes from downtown, the lakefront, top restaurants, shopping, nightlife, and easy public transit access.

Value · Location · Bathroom

Level ◆ Brand New Luxe One Bedroom

Designed with you in mind, our One Bedroom Suites range from 560 – 698 sq ft of spacious living space boasting fully-equipped kitchen, comfortable living area, spa-inspired bathroom, bedroom with king bed and open-air balcony. Perfect for couples and corporate travelers alike, all suites also feature in-suite laundry, premium appliances, flat-screen TV with cable, complimentary WiFi and local calling. Welcome to the suite life.

Value · Location · Check-in

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 · Kitchen

Urban Oasis in Vibrant Gold Coast

Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, we are perfectly situated in the middle of the action for your Chicago adventure. ***Please note that from March until the end of September 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***

Location · Family · Indoor spaces

Hancock Lookout|Steps to Beach&Transit, CHI Views

Wake up in Chicago’s Gold Coast with stunning views of Lake Michigan and the Hancock Tower. This top-floor high-rise apartment offers modern style, natural light, and a prime location. Walk to Oak Street Beach, luxury shopping, fine dining, and the Magnificent Mile. Enjoy skyline sunsets, lake breezes, and the perfect mix of comfort and convenience for an unforgettable stay.

Value · Location · Quiet

Luxury Central in OldTown With Balcony

The whole group will enjoy easy access to everything from this centrally located place. There are 1 queen bed in the bedroom, 1 queen sofa bed, and 1 single pull out sofa bed in the living room area. The unit is located on 2nd floor. Inside of the unit Brand new unit with hidden lighting, expose bricks, balcony face to Schiller Street. Full kitchen if you prefer to cook.

Location · Value · Sleep quality

Breathtaking & Chic Oasis Loc in Desirable Old Twn

Enjoy a stylish experience at this centrally-located place. Our stylish 1-bedroom Airbnb, catering to all kinds of travelers. Whether you're looking for a restful stay, a productive workspace, a central hub to explore Chicago, a night of fun at the bars and nightlife, or a snug spot to unwind and connect, our place has everything you need.

Location · Value · Kitchen