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Waterfront vacation rentals in Downtown Chicago

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Top-rated waterfront rentals in Downtown Chicago

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A spacious living area features two gray sofas and a wooden coffee table, positioned on a light blue area rug. Large windows provide natural light, complemented by modern wall art and a potted plant, creating a comfortable and inviting space.

Apartment in Chicago

4.82 out of 5 average rating, 184 reviews

The Lakefront Lookout (2BR)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, Navy Pier, Riverwalk, Soldier Field, The Field Museum, Oak Street Beach, and more. Additionally, guests are merely blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

The living room features a comfortable sectional sofa adorned with accent pillows, positioned in front of a large television. A striking wall mural depicting Earth adds character. Natural light streams through expansive windows, illuminating a round coffee table atop a soft area rug.

Condo in Chicago

4.94 out of 5 average rating, 109 reviews

PING-PONG Free PARKiNG 10 min-Downtown Sleeps 10

ONE FREE INDOOR & SAFE PARKING SPOT INCLUDED! The building is next to a bus stop that brings you right into downtown! You would enjoy staying in the spacious 1800 sq ft with 10 ft high ceilings. 2 bedroom/2 bathroom apartment with ZERO STAIRS to get inside! It is an excellent solution for elder people and families with kids or maybe just a group of friends coming to have fun at the UNITED CENTER sports event or tourists as well as business folks or doctors to attend McCormick Place conferences.

A spacious bedroom features a large bed with soft bedding and multiple pillows. Dark walls create a cozy ambiance, complemented by stylish artwork. A glass table and chairs are visible, along with a modern ceiling fan and a bright window providing natural light.

Apartment in Chicago

4.95 out of 5 average rating, 79 reviews

Loyola & Lake -3br/2bth close to the Lake & Loyola

Amazing lake views from 2 outdoor spaces! This spacious 3 bedroom, 2 bath unit has a large front balcony looking out to the lake and also a rear deck with lake views as well. The unit was recently renovated and has updated kitchen, bath & lots of entertaining space. In unit laundry and detergent included. Lots of books and games to keep you entertained! Walking distance to restaurants and bars. Starbucks is at the end of the block. Kayaks/paddle boards available for rent (May 1-Oct 15).

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

4.83 out of 5 average rating, 192 reviews

Historic lux Townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the luxurious Gold Coast of Chicago. Perhaps the BEST location in Chicago! Located on one of the desirable & famous streets in Chicago, this property is a 5 min walk from the Gold Coast beach where you will see Lake Michigan in all of its glory. Not to mention the proximity of this property to the subway and within walking distance of Magnificent Mile. It is the perfect place to stay for the adventurous and also 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.

Apartment in Chicago

4.92 out of 5 average rating, 220 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.

Condo in Chicago

4.92 out of 5 average rating, 222 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This 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. Dogs only. Parking free on street or one spot for a fee.

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

4.87 out of 5 average rating, 186 reviews

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!

A modern chef's kitchen is shown, featuring an island with seating for four. Sleek dark cabinetry contrasts with light countertops and stainless steel appliances. A bowl of fruit adds a touch of color, while glass pendant lights provide illumination above the island.

Condo in Chicago

4.94 out of 5 average rating, 107 reviews

Modern MAG Mile 2BD/2BA (+Parking/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 - Parking spot on-site in/out access!! - Tranquil rooftop overlooks Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows

The living area features a light-colored sofa paired with two cozy armchairs. A round coffee table sits at the center on a colorful area rug. Natural light floods the space through two large windows, and decorative plants are placed on the windowsills.

Apartment in Chicago

4.8 out of 5 average rating, 187 reviews

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!

A spacious bedroom features a king-size bed dressed in white linens, accented by a mustard yellow throw. Nightstands with lamps are positioned on either side of the bed. A decorative rug adds softness to the warm-toned wood flooring, with natural light streaming from the patio doors.

Townhouse in Chicago

4.93 out of 5 average rating, 119 reviews

Old Town/Lincoln Park Luxury Home Garage & Rooftop

Old town luxurious townhouse with rooftop, patio and attached garage (with Level 2 electric car charger for any type of electric car). The extra wide floor plan allows for 4 large bedrooms and 2.5 bathrooms spread over 4 levels of living. One block away from Brown Line station and 4 blocks away from Red Line station and best of Lincoln Park shopping. 10 minutes walk to North Avenue Beach or Lincoln Park Zoo. 5 minute walk to Second City, Zanies and Old Town dining & nightlife.

A covered patio area is visible, featuring a gas grill, comfortable seating on a sectional sofa, and dining tables. Lush greenery and a lake can be seen in the background, with soft sunlight filtering through the trees.

Home in Downers Grove

4.97 out of 5 average rating, 30 reviews

Lakefront Getaway Home! Amazing View! Hot tub! Ski

INCREDIBLE 5,519 sq. LAKEFRONT HOME with GORGEOUS VIEWS. 30 Minutes Away From Downtown Chicago. 7 Bedrooms, 9 Beds, 2 Additional Sofa Beds & 4 Baths. Fits 20 guests by request. PRIVATE DOCK and PATIO/BACKYARD Right on BROOKERIDGE LAKE. UNICORN ISLAND FLOATING RAFT, KAYAK, PADDLE BOAT, FISHING & MORE. BrookeRidge Private Jet Airport in the Same Park. Indoor Entertainment Including POOL TABLE, AIR HOCKEY, PING PONG, DARTS, CARD GAMES, GAMING CONSOLE & KARAOKE 🎤

Townhouse in Westmont

4.87 out of 5 average rating, 129 reviews

Westmont 3/2 duplex Fire sunsets, Firepit, lake

Near great shopping and dining. Enjoy wonderful sunsets and quiet lake activity. Fully Stocked 20 acres lake with a neighborhood beach next door. Easy commute to downtown while enjoying the peace and quiet. Feel like you are on vacation every day. Perfect for a staycation. Cleaned to Cdc standards. This duplex is a gem in Western suburbs! Pet friendly (fee). Fire pit (bring Wood), paddleboat, kayaks. Grill and fully stocked kitchen.

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Popular amenities for Downtown Chicago waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Apartment in Chicago

5 out of 5 average rating, 4 reviews

Luxurious Lincoln Park Home with Gourmet Kitchen

A stylish bedroom features a four-poster bed centered on a spacious wooden floor. Soft lighting from string lights creates a warm ambiance. A closet is visible in the corner, providing additional storage space, while natural light enters through a nearby window.

Apartment in Chicago

4.93 out of 5 average rating, 30 reviews

Sheridan Beach Apartment

Apartment in Chicago

5 out of 5 average rating, 4 reviews

The Wine Down

Apartment in Chicago

4.98 out of 5 average rating, 43 reviews

Cozy Chicago Apartment next to the River

Apartment in Chicago

5 out of 5 average rating, 19 reviews

3BR Luxury Modern Apartment

Apartment in Chicago

4.77 out of 5 average rating, 22 reviews

2b2b by Water Tower and the Lake

A spacious living room features a cozy seating area with two leather sofas facing a modern TV stand. A light-colored coffee table is positioned between the sofas, and a decorative painting hangs above the fireplace. Large windows with blinds allow natural light to fill the space.

Apartment in Chicago

4.86 out of 5 average rating, 65 reviews

Elegant 2-bed/2-bath in the heart of Uptown

A bright and open living area features a spacious blue sofa and a round dining table with four chairs. A flat-screen TV is mounted on the wall, and large windows allow natural light to fill the space. The modern kitchen is equipped with sleek appliances.

Apartment in Evanston

4.93 out of 5 average rating, 80 reviews

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

Waterfront house rentals

Private room in Chicago

4.87 out of 5 average rating, 129 reviews

Renovated space in a historic row house.

Home in Prospect Heights

4.91 out of 5 average rating, 53 reviews

Lakefront Prospect Heights Home: Ice Fish On-Site

Home in Chicago

4.9 out of 5 average rating, 48 reviews

CasaNova Modern City Living

The exterior of a red brick building is displayed, featuring large arched windows and a central entrance with steps leading up to it. Flanking structures are visible, showcasing a blend of architectural styles, while a sparse lawn with minimal landscaping is present in the foreground.

Home in Chicago

4.84 out of 5 average rating, 75 reviews

Lake Home-3 blocks to beach/harbor 10 min 2 Loop!

Home in Des Plaines

4.69 out of 5 average rating, 35 reviews

House 1 minute from O'hare Airport

A spacious wooden deck extends toward a serene lake, offering scenic water views. A table with several chairs is shaded by a large umbrella, providing a comfortable outdoor seating area. The surrounding landscape features trees with autumn foliage, enhancing the tranquil setting.

Home in Westmont

4.81 out of 5 average rating, 31 reviews

Cozy 5-bedroom with lake views and spacious deck

A welcoming family room is showcased with polished wooden flooring and warm ambient lighting. A plush seating arrangement includes a large sofa, accompanied by decorative lamps and vibrant wall art. A coffee table rests in the center, creating an inviting space for relaxation.

Home in Des Plaines

4.79 out of 5 average rating, 186 reviews

Exotic House - Few minutes from O'Hare and Chicago

Home in Chicago

4.61 out of 5 average rating, 36 reviews

Beautiful 3 Bedroom TownHome in Rogers Park

Waterfront condo rentals

A modern kitchen with white cabinetry features stainless steel appliances, including a refrigerator and microwave. An island with seating for three is complemented by decorative vases of flowers. Natural light fills the space through large east-facing windows.

Condo in Chicago

4.89 out of 5 average rating, 153 reviews

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

A cozy sleeping area features a spacious bed dressed in a gray coverlet, complemented by two accent pillows. A reclined chair in a warm tone sits nearby, with a decorative throw and artwork displayed above the bed. A colorful area rug adds texture to the polished floor.

Condo in Chicago

4.8 out of 5 average rating, 25 reviews

Lovely condo studio

A cozy living area features a charming fireplace framed by a reddish-brown brick wall. Two elegant chairs and a stylish sofa are positioned around a geometric coffee table, creating a welcoming space. Large windows with light yellow curtains allow natural light to fill the room.

Condo in Chicago

4.87 out of 5 average rating, 15 reviews

HUGE Modern, w/ Home Office, Chef's Kitchen, Patio

A well-lit hallway is adorned with framed artwork and a stylish console table. At the end of the hallway, a cozy seating area with a round dining table and four chairs is visible, illuminated by natural light from large windows.

Condo in Chicago

5 out of 5 average rating, 55 reviews

Where you want to BE! Stylish, Comfy, Luxe

A spacious living area is presented, featuring a gray sectional sofa adorned with decorative pillows. A glass coffee table sits at the center, complemented by two black accent chairs. Natural light filters through the nearby windows, enhancing the room's openness.

Condo in Chicago

4.79 out of 5 average rating, 19 reviews

Spacious Wicker Park Hideaway with Parking!

A bright living area features a blue sectional sofa facing a television. Two armchairs are positioned across from the seating area, with a glass coffee table in the center. Natural light streams in through two large windows, and a green plant adds a touch of nature.

Condo in Chicago

4.85 out of 5 average rating, 89 reviews

River North Hideaway w/Amazing Views and Parking

Condo in Chicago

4.83 out of 5 average rating, 36 reviews

Bronzeville Tribe Palace Loft

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