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.

Location · Family · Indoor spaces

The Picasso: #1 Chicago Location

Welcome to The Picasso on Lincoln Park… Chicago’s BEST location! Steps away from the beach, zoo, cafes, nightlife, and easy Uber access for short 5-min rides to Michigan Ave & Wrigley Field! Recent rehab with charming art house decor. Professionally managed and sanitized. Historic landmark building, with a junior-suite feel (500 sqft), lofted open-air bedroom with queen bed, 3rd floor. WiFi, shared coin operated laundry, excellent heat/AC, free street parking or paid parking lot 2 blocks away.

Location · Checkout · Quiet

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 completed contactless from your phone, or in person with our 24/7 on-site front desk. Virtual Front Desk support is available by text anytime.

Family · Location · Kitchen

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.

Family · Value · Heating

Modern Corner 2BR in Streeterville | Roof Deck | L

Stunning 1,200 square foot apartment with oversize windows, an open layout, and city/lake views in multiple directions. This bright and modern two bedroom, one bathroom corner unit is perfect for travelers looking for a stylish escape in the sky in downtown Chicago just off the Magnificent Mile and the lakefront. The building has great amenities including an amazing rooftop terrace with 360 degree views of the skyline and the lake. This is the best location in the city!

Location · Value · Parking

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 · Hospitality

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.

Location · Value · Indoor spaces

Level Junior Two Bedroom Suite | Fulton Market

Two bedroom, two bathroom suite featuring a king bed, queen bed, and sofa bed. Maximum occupancy is 4. Enjoy access to over 32,000 sq ft of unrivaled lifestyle amenities, including a seasonal outdoor pool, a relaxing hot tub, and a state-of-the-art fitness center. Take in stunning views of the Chicago skyline from our Cloud Lounge, grill meals at the BBQ stations, and enjoy movie or game nights in the media room.

Location · Family · Parking

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 · Solo travel

Bright & Cozy 1 Bdrm • Free Parking

Here for work, visiting family or just a Chicago getaway? Looking for stylish, comfortable accommodations close to Downtown Chicago? Look no further! This pet-friendly 1 bdrm Bridgeport flat has everything you need: bright open spaces, spacious kitchen, comfy bedroom, WiFi & FREE street parking! All located on a quiet residential street close to downtown. What more could you need??

Family · Value · Hospitality

Modern 3BR Apartment Near North Ave Shops

Welcome to your bright and spacious 3-bedroom Chicago retreat. Enjoy an open living area, fully equipped kitchen, and cozy bedrooms designed for both comfort and privacy. Large windows fill the space with natural light, while modern furnishings and soft tones create a calm, welcoming feel - perfect for families, groups, or business travelers seeking room to relax and recharge.

Value · Family · Kitchen

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 · Indoor spaces