Beachfront holiday rentals in Chicago

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.

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

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

Historic Coach House in Evanston Near Beach & Town

Stay in the Coach House of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire coach house which is renovated and includes a large bedroom with king bed and desk, a sun-filled living room/dining room, a full bath with claw-foot soaking tub and shower and a kitchen with amenities. The space can be equipped with an air mattress for an extra guest. Also available is a 3rd floor guest suite in the main house.

Gold Coast Pristine 3BD|2BR| Patio |Parking| Beach

FREE GARAGE PARKING! Garage Clearance 6ft. Step into luxury in this modern loft with 3 bedrooms, 2 bathrooms and a private patio with breathtaking views. Experience the feeling of being at home in a bright and spacious haven amidst Chicago's most sought-after neighborhood "Gold Coast" This centrally located gem is situated within walking distance of much of Chicago Downtown's exquisite dining, upscale boutiques, popular tourist destinations, and just a stone throw away from Oak Beach.

Gym | Lake | 3b2b

Location, location and location! Very spacious and simple downtown 3b2b apartment is centrally located right beside the iconic Chicago’s Water Tower and John Hancock Center. *3rd bedroom separated by divider so no walls and not soundproof. Not only are you right by the Magnificent Mile, you’re only 1 block away from the Lake and Oak Street Beach!! Walkable distance to Navy Pier and all the beautiful tourist places in downtown Chicago. Close to everything and in the best neighborhood.

Entire APT in heart of Lincoln Park&Lake and beach

This home is located In the heart of Lincoln Park near Old Town Triangle and near the beach in the core of Chicago. Ideal people who want to stay in the vibrant beautiful city. Close to parks, beach, lake, subway station, shops, restaurants and night life! Entire one bedroom apartment with spacious (850 sqft) and beautiful interior design. As you can pick up the key from self check-in box, you can check in and out anytime. Check in time is 2pm and check out is 11am. R22000082349

Rooftop | Villa | Events

Gorgeous designer space, a mini Villa but large throughout making it light, bright, airy with feelings of calm and tranquility. Party Backyard/Rooftop Indoor features Luminaire Chandeliers, 10 feet ceilings, Grand Piano, Music Box etc. Huge backyard offer spaces to entertain. You’re booking a private residence: Three levels of home exclusive to your guests/party. Guest can view cameras of all entrances; Roof deck, Front, Back & Alley via Monitor (HDMI-1) 24/7 record.

Downtown | Magnificent Mile | 3B by Lake - OOTS

New Listing Location, location, location! Welcome to this modern, luxury, newly renovated, downtown apartment with 3 bedrooms! Experience the city being located in Chicago’s most-sought after neighborhood - central river north, by Magnificent Miles on high end brands’ shopping district. Just 5 min walk to the beach! The whole group will enjoy easy access to everything from this centrally located place. ***This listing requires stairs to 2nd floor. Some blinds missing.

Woodlawn Oasis

Welcome to Woodlawn Oasis! Come and enjoy the charm and warmth of this fully remodeled and furnished apartment with original artwork! Just 5 minutes from our beautiful Chicago lakefront, the prestiges University of Chicago, and soon to be Tiger Woods golf course and President Obama library. Also, 10 minutes from Chicago museums, Soldier Field (Chicago Bears), Guaranteed Rate Field (Chicago White Sox) and the fabulous night life of Downtown Chicago!

Sunny Lakeside Apartment in Rogers Park

Relax in this sunny, tranquil 1BR apartment just steps from Lake Michigan! Enjoy easy beach access, walk to local cafés and shops, or hop on the train—downtown is just 20–30 minutes away. Loyola University is a 15-minute walk, and Northwestern is a 15-minute drive. Bright, peaceful, and fully equipped, this cozy space is perfect for a weekend getaway, work trip, or campus visit. Feel at home by the lake in one of Chicago’s most vibrant neighborhoods!

Only Urban Beach House in Chicago

Why stay in a hotel or dorm when you can have your own house! The Urban Beach House of Rogers Park, Chicago’s only urban beach house, has 4 bedrooms, 3 full baths, and is loaded with features that make it the perfect place for vacationers, students, faculty, family and gatherings of all kinds. Steps from the sandy beaches of Lake Michigan, walking distance from dozens of restaurants and shops, and minutes from 3 train stations and a Divvy bike station.

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!