Vacation rentals in Gold Coast

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OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)

Welcome to this Old Town Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Wells St. - Close to every popular attraction that makes Chicago so great - Room for reg-size SUV in private driveway! - Luxurious interior design - Tranquil rooftop w/ grill - Fast WiFi - Pillow-top Bamboo mattress in each master en-suite - State of the art kitchen - Exceptional workspace - 5 minute walk from red line (CTA L) We look forward to hosting you!

Chic Apt on Bar & Restaurant Street, City Life,

Our studio apartment at W Schiller St. is perfectly located in the heart of Old Town. Situated on the 3rd floor, it offers a comfortable accommodation experience with amenities like shampoo, body wash, conditioner, paper towels, toilet paper, bath towels, face towels, and hand towels. A Keurig coffee maker with coffee capsules is also provided. Enjoy bars, restaurants, and entertainment nearby, with the lake just a short walk away. It is an ideal starting point for exploring the city.

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.

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Explore Lincoln Park from a Polished Apartment

A bright, cozy, large studio in the heart of Lincoln Park! You enter with a keypad code which we give you a few days prior to your stay. You are steps away from Armitage Ave. and Halsted St. for walkable grocery stores, shops, restaurants and cafes, plus Red and Brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment with free residential parking stickers or an onsite garage space for $25/night.

Golden Suite on State|Steps to Oak Beach & MagMile

Wake up in the heart of Chicago’s glamorous Gold Coast on iconic State Street. Just a short walk from Oak St Beach and Lake Michigan, this stylish high-rise retreat places you steps from the city’s best dining, boutiques, and famous attractions. Spend the day exploring tree-lined streets and lakefront paths, then return to a bright, modern space perfectly positioned to experience Chicago like a local. A central stay where convenience, charm, and city energy meet.

Stylish Gold Coast 3BR Apt | Walk to Grocery&Cafes

!!!FREE GARAGE PARKING!!!! Stay in the heart of Chicago’s Gold Coast in this stylish 3-bedroom/ 2 bath apartment on Dearborn. Designed for comfort and convenience, it features a bright living room, fully equipped kitchen, smart TV, WiFi, and in-unit laundry. Steps from groceries, cafes, and restaurants, and just minutes to Oak Street Beach, Magnificent Mile, and downtown. Perfect for families, friends, or business travelers seeking space and a prime location.

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!

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.

Charming Historic Row Home | Lincoln Park

Experience historic charm and modern luxury in the heart of Lincoln Park. This updated 1870s row home features a private gated brick courtyard, chef’s kitchen with Wolf & Sub-Zero appliances, and full home automation. Unwind by the cozy wood-burning fireplace or retreat to 3 quiet bedrooms with newly renovated baths. Steps from Chicago’s best dining, boutique shopping, and transit—your perfect city getaway!

Luxury Designer Apartment 803| Gold Coast/Old Town

NEW APARTMENT IN THE HEART OF GOLD COAST and OLD TOWN! Enjoy your own luxury apartment in Chicago's Gold Coast and Old Town-the city's center of nightlife, restaurants, and shopping. In the newly renovated building, your 2 bedroom/2 bathroom penthouse offers some of the best views in all of Chicago. The highly secure building includes elevator, rooftop/sundeck, full gym, lounge and is perfect for all.

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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.***

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Old Town Condo: Private Terrace & Garage Parking

Experience vibrant Chicago from this modern 2-bed, 2-bath Old Town condo. Perfect for families or professionals, it features a private terrace, gourmet kitchen, dedicated workspace, and a rare dedicated parking spot. Soaring 13-ft ceilings and stylish design create a light-filled urban retreat just steps from Lincoln Park, Second City, and North Avenue Beach. Comfortably sleeps 4.