Waterfront vacation rentals in Chicago

Grant Park-10 min Free P-Spot EV&Balcony Sleeps 12

Steps from the United Center & Near Downtown Chicago. Modern 3BR, 2BA apartment sleeps up to 12 guests with 8 cozy beds and a private ensuite with heated floors. ✔️ Fully accessible – zero stairs + elevator access ✔️ Free secure indoor parking (EV outlet next to spot) ✔️ Shared rooftop deck with stunning skyline views ✔️ Fast Wi-Fi, streaming-ready TVs, and a fully stocked kitchen - Walk to Pete’s Fresh Market (5 min) - Reach Damen Green Line in 10 min walk - 10 min Uber to Downtown Chicago

Historic luxury townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after locations in the city! Located on one of Chicago’s famous streets, you’ll be a 5-minute walk from the historic Gold Coast beach and intimate views of Lake Michigan. The property is also within walking distance of the subway, where you can connect to the L trains, and the Magnificent Mile. It is the perfect place to stay for adventurous travellers and those who fancy a beach in the City!

Stone Mansion Sleeps 10-20 Free parking & TV

Giant, 4 bedroom, 2,300 square feet apartment on 2nd floor, near Red Line Train, bars, cafe's, shopping, restaurants, Lakefront and everything else Chicago has to offer. Large living room with bar area, TV and fridge for socializing before hitting the town. Dining room has a large table and 8 chairs. 4 bedrooms with 2 private rooms with king beds and one with a double bed. 4 futons for in the living room for extra sleeping space two (2) parking spots in the west facing garage on premises.

Gold Coast Home|Rooftop |PoolTable |Parking |Views

Luxurious Gold Coast Townhome – Offers Indoor Games, Rooftop, Parking & More! Experience the best of Chicago in this stunning 4,000 sqft Gold Coast residence. Perfect for groups of up to 12, this home features 4 spacious bedrooms, 4.5 bathrooms, and a ceiling-length window with incredible views. Enjoy a variety of indoor games and make use of the convenient rooftop. Whether you're here for leisure or work, this property offers modern amenities and unforgettable comfort in the heart of City

Spacious & Elegant N Side Apt Near Beach & Transit

This spacious 1-bedroom apartment, just 1 minute from Marion Majony Griffin Beach, offers comfort and convenience for solo travelers, couples, or small families. Enjoy a fully equipped kitchen, cozy pull-out couch, and a dedicated workspace perfect for remote work or studying. Free street parking is available, or take public transit just a block away to the Red Line for easy access to the city. With its prime location and thoughtful amenities, we warmly welcome all travelers to our listing.

Spacious & Stylish 2BR-2BA Apt Steps from The Bean

Enjoy this comfy, renovated and super spacious 2BR and 2BA apartment in the heart of Chicago's Loop with views of Lake Michigan. Surrounded by the most popular stores and restaurants, this unbeatable location is less than a one-minute walk to Michigan Ave, Millennium Park, State St. Shopping, The Chicago Theatre and Chicago’s landmark, ‘The Bean'. It is an ideal location to move around in public transportation, as all CTA lines and plenty of bus lines are just within two blocks!

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This cozy AirBnb is perfectly situated. A beautifully clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation & restaurants, red line "El" trains & bus routes. Apt has private, queen bedroom, en suite full bathroom, living room w/queen sofa bed, TV, dining table, & partial kitchenette. NOTE: No full kitchen.

New renovation|1BR|Stylish|Modern|Next to the Lake

Experience the best of Evanston in our cozy 1BR/1BA apartment near Lake Michigan. Enjoy a fully equipped kitchen, a comfortable bedroom with a queen-sized bed, and a clean bathroom. Explore the nearby beaches, stroll along the lakefront path, and discover the vibrant downtown area with its shops and restaurants. Easy access to public transportation allows you to explore downtown Chicago. Book your stay now for a memorable Evanston getaway!

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)

Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.