Beachfront vacation rentals in North Side

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!

Buena Vida Casa

Welcome to Buena Vida House. Step into a beautifully updated unit where every detail has been thoughtfully designed to create a peaceful, stylish getaway. This unit features fresh finishes, with 2 bedrooms equipped with queen beds, and a unique blend of beachy and boho vibes. Just steps from the lakefront, ideal for morning jogs or simply soaking in the beauty of Chicago. This one-of-a-kind space offers comfort, charm, and convenience in one of Chicago’s most walkable and scenic neighborhood

Historic Gilded Age Gold Coast Mansion w/ Deck

RENT WITH CONFIDENCE FROM SUPERHOST WITH OVER 800 FIVE STAR REVIEWS One-of-a-kind opportunity to rent a historic Gilded Age Chicago Gold Coast mansion. All modern amenities meet Romanesque Revival style at this huge 5-bedroom Graystone. Steps away from Rush St restaurants, Division St nightlife, Oak Street Beach, and Michigan Avenue shopping. Enjoy central air & heat, 3 fireplaces, a fully stocked kitchen, balcony and an attached garage. Pets are welcome. What else could you possibly need?

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.

A Sunny, Well-Kept & Comfy Studio in Gold Coast

Stay in a cozy, clean, and bright Gold Coast studio right in Chicago’s most iconic neighborhood. Rest comfortably in the well-furnished space, complete with a seating area and a full kitchen for convenient cooking. The bathroom is stocked with fresh towels and essential toiletries. With Oak Street Beach, Michigan Avenue shops, dining, nightlife, and public transit only moments away, getting around is effortless. Perfect whether you’re here for a quick trip or an extended visit.

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.

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.

Charming Retreat in Evanston Right Next to Beach

3rd-floor unit with three flights of stairs. Older building with radiant heat managed by the building. Welcome to your ideal Evanston getaway. Located near Northwestern University and steps from South Boulevard Beach, this inviting space offers comfort and convenience. Enjoy a bright, furnished interior, a fully equipped kitchen, and easy access to downtown Evanston’s shops, restaurants, and cafés. Walk to the beach and enjoy a peaceful neighborhood atmosphere.

Guest Favorite Escape Next to the Beach

1st-floor unit with one flight of stairs. Older building with radiant heat managed by the building. 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 bed, and a clean bathroom. Explore nearby beaches, stroll along the lakefront, and discover vibrant downtown shops and restaurants. Easy public transit to downtown Chicago. Book now for a memorable Evanston getaway!

Gold Coast 1BR – Easy Downtown Access

Settle into Chicago’s Gold Coast, a distinguished and charming neighborhood just a short walk from downtown. Steps away, you’ll find Oak Street Beach, the lively restaurants of Rush Street, high-end shopping along Michigan Avenue, and an inviting mix of cafes, boutiques, and nightlife. With public transit nearby, exploring the city and surrounding areas is effortless. Inside, enjoy a cozy and well-appointed space crafted for both comfort and convenience.