Beachfront vacation rentals in North Side

4.83 out of 5 average rating, 217 reviews

The townhouse stands elegantly among lush greenery, featuring a classic facade with black-framed windows and a welcoming entrance. A wrought-iron fence complements the landscaped front area, while a tree provides shade along the sidewalk.

Townhouse in 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!

The historic stone façade of the building features intricate architectural details, with large arched windows and a welcoming entrance. Flower pots are displayed on the balcony, and a wrought iron fence surrounds the property, adding to the charm of the exterior.

4.92 out of 5 average rating, 258 reviews

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.

4.87 out of 5 average rating, 198 reviews

A spacious living area features a large sectional sofa facing a media unit with a TV, accompanied by a coffee table. A dining table with four chairs sits nearby. Floor-to-ceiling windows provide bright natural light and a view of adjacent buildings.

Condo in Chicago

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!

Top guest favorite

5 out of 5 average rating, 19 reviews

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

4.94 out of 5 average rating, 124 reviews

The historic manor house features a rich red brick facade adorned with lush green ivy. The spacious porch extends from the building, complemented by well-maintained gardens that enhance the inviting exterior. Large windows provide ample natural light, creating an open and airy ambiance.

Guesthouse in Evanston

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.

A private patio provides a cozy seating area featuring a 3-seater sofa and two accent chairs. A round coffee table sits in the center, with the urban street view visible beyond the wrought iron railing.

4.92 out of 5 average rating, 77 reviews

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 dining table is set for an intimate meal, featuring a white tablecloth and stylish silverware. A single red rose in a glass vase is positioned beside a bottle of wine, with two glasses ready for use. A framed artwork of a street scene adorns the light-colored wall.

4.55 out of 5 average rating, 120 reviews

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

4.65 out of 5 average rating, 55 reviews

A grand piano occupies the foreground, showcasing a polished surface that reflects light. Behind it, a spacious area is visible with a row of blue chairs and a ceiling adorned with modern chandeliers, highlighting the open and elegant design of the indoor space.

Villa in Chicago

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.

A cozy living area features a brown sofa adorned with patterned cushions, paired with two armchairs. A round coffee table sits centrally, surrounded by natural light from windows. A large artwork of a roaring tiger dominates one wall, while a potted plant adds a touch of greenery.

4.84 out of 5 average rating, 61 reviews

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!

A cozy living area features a light-colored sofa and a wooden coffee table, complemented by a vibrant patterned rug. Natural light enters through a large window with sheer curtains. A small desk and chair are positioned nearby, with plants adding a touch of greenery.

4.85 out of 5 average rating, 34 reviews

New place to stay

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!

A charming gray two-story home features a welcoming yellow front door. The porch is adorned with potted flowers, and large windows allow natural light to enter. The surrounding landscape includes well-maintained shrubs, creating an inviting approach to the entrance.

Home in Chicago

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.