Vacation rentals in Near North Side

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 · Beach

Luxury Loft Collection 01 - Terrace - River North

BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious building in bustling River North-the city's center of main nightlife and restaurants. This ultra high-end apartment features a private elevator, private terrace, free secured parking, 24 hour doorman, 3 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

Location · Family · Wifi

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 · Access

Top guest favorite

Guest favorite

Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D

Private 2BR apt. in vintage 3-flat in the heart of Chicago's Michigan Ave/Gold Coast neighborhood. Fantastic locations steps from world-class shopping and restaurants, Oak St. beach, and public transportation (L trains, express bus). Includes A/C, washer-dryer, super-fast wi-fi, smart TV, and workspace. Hourly rate garage parking next door. Note: Guests must walk up one flight of stairs. Light sleepers should bring earplugs as there are noises typical of a big city.

Location · Family · Condition

Stunning Gold Coast Studio

This apartment in the Gold Coast is close to everything, making it easy to plan your visit. Conveniently located near the Loop and just around the corner from the Clark/Division Red Line stop and CTA Bus 156, 70, 22 and 36 lines. Blocks away from Oak Street Beach, Magnificent Mile, Navy Pier and Museums. Neighboring the Loop, River North, Near North, Streeterville, Old Town, Lincoln Park, Pulaski Park, Lake View, River West, and New East Side!

Location · Value · Comfort

City king

Step into the city king room where inspiring views of downtown and a spacious cozy king bed invite you to relax in style. Enjoy smart amenities like a Nespresso coffee machine, a 55 inch flat screen TV, a smart fridge and a work desk. Contemporary luxury design and thoughtful details like a hand held steamer hair dryer and laptop sized safe make this a perfect home base whether you are exploring the city or enjoying a quiet night in.

Location · Value · Cleanliness

Chicago's Magnificent Mile Stay + Dining & Gym

Tucked just off the Magnificent Mile, Hotel Saint Clair gives you front-row access to Chicago’s must-sees—think Navy Pier, Millennium Park, and late-night eats around the corner. Sip your morning coffee, grab your camera, and hit the lakefront in minutes. The rooms are pet-friendly, WiFi’s on the house, and everything you want to see is walkable. It’s your laid-back launchpad for big city adventures.

Location · Value · Accuracy

Top guest favorite

Guest favorite

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.***

Family · Value · Check-in

Standard king

Standard room offers a tastefully decorated space with a plush king bed designed for your comfort and relaxation. Enjoy modern amenities like WiFi, smart TV and an in room safe along with coffee and tea making facilities. Thoughtful touches create a welcoming atmosphere for both work and leisure making it an ideal choice for any traveller. Unwind and recharge in style during your stay.

Location · Family · Checkout

The Burlingham - A Bespoke Gold Coast Retreat

Located in the heart of the prestigious Gold Coast neighborhood, a unique professionally designed space that exudes sophistication. Nestled in a quiet boutique elevator building, the unit boasts spectacular, unobstructed, south-facing city views and is drenched in light throughout the day. No detail has been overlooked and every desired convenience has been anticipated.

Location · Getting around · Indoor spaces

One queen bed non smoking

One queen bed non smoking features a queen bed, air conditioning, private bathroom with separate shower and bathtub, bathrobes, hair dryer, toiletries, free wifi and LAN, flat-screen TV with satellite/cable, iPod dock, coffee/tea maker, blackout curtains, desk, and daily housekeeping. Accessible features include close-caption TV, TTY/TTD compatibility, and visual alarm.

Location · Family · Breakfast

★Downtown★Self Check-In★Smart TV★Walk Score 98

Amazing, historic, single-family home in Chicago's Gold Coast. Walk to nightlife on Rush and Oak, Magnificent Mile, Oak Street Beach, Lakefront, Northwestern Memorial Hospital, and Navy Pier. Steps to amazing restaurants, bars, and museums. The area is filled with restaurants and stores within a 5-minute walk. Taxis can be hailed from right outside the door.

Location · Value · Parking