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Mansion vacation rentals in Chicago

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Top-rated mansion rentals in Chicago

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Top guest favorite

A comfortable living area showcases a modern design with a large flat-screen TV mounted on a stone feature wall. Soft lighting highlights a cozy seating arrangement, including a plush sofa and two armchairs. A decorative coffee table sits in the center, contributing to a welcoming atmosphere.

Apartment in Albany Park

4.97 out of 5 average rating, 157 reviews

NorthSide Chicago duplex 5-BD,2King size-free park

5-BD, 2-BR duplex; a combination of first floor and garden units. Just a 3-minute walk from the train, our property is the perfect place for your big gathering. Sleeps up to 12 guests with indoor Jacuzzi, full kitchen, free indoor parking( 1 car), and private patio. Access to grill, fire pit with big screen TV, and sound system. Keyless check-in and 24/7 active security cameras. Don't miss out on experiencing the best of Chicago from our beautiful and convenient duplex unit. Book your stay now!

An open-concept living space features a large sectional sofa in front of a vibrant area rug, with exposed wooden beams overhead. Large windows allow natural light to fill the room, revealing glimpses of the dining area and a staircase adorned with artwork.

Home in Logan Square

4.95 out of 5 average rating, 154 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

Welcome to The Grand Kimball Lodge, a truly unique getaway featured in Architectural Digest's "21 Best Chicago Airbnbs for Your Next Windy City Trip." Located in the heart of Logan Square, this charming loft combines rustic elegance with modern comforts. With 4 themed bedrooms, 3 bathrooms, a chef’s kitchen, & spacious living & dining areas, it’s the perfect space for families, friends, & small groups to gather & make lasting memories. Visit my owner’s profile page for a 20-person listing too.

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.

4.83 out of 5 average rating, 210 reviews

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!

Top guest favorite

A modern living area is showcased with large windows allowing natural light to fill the space. A plush gray sofa and stylish chairs are arranged around a circular glass coffee table, complementing the dark wooden built-ins and fireplace that house decorative items.

Home in Wicker Park

4.97 out of 5 average rating, 111 reviews

UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)

Escape into this Wicker Park Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Division St. - Close to every popular attraction that makes Chicago so great - Luxurious interior filled with natural light - Open-floor plan for entertaining! - City skyline views from top floor! - Fast WiFi (1,000 mbps) - Large attached garage! - Beautiful custom built-ins - Next to modern park and playground! - 10 minute walk from blue line (CTA L)

Top guest favorite

The modern kitchen showcases sleek white cabinetry and a spacious island topped with a white marble surface. Stainless steel appliances, including a gas stove and a refrigerator, are complemented by glass-front cabinets displaying elegant dishware. Soft blue lighting highlights the room's contemporary design.

Home in Portage Park

4.97 out of 5 average rating, 117 reviews

Ultra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14

Treat yourself to this Chicago getaway with 14 of your friends & family. Be inspired to create culinary delights in our celebrated 5 stars outdoor kitchen. Reboot & relax in each of our thoughtfully designed powered by SOLAR ENERGY throughout. After a memorable night in OR an adventurous night out you will ask yourselves, 'Why don't we do this more often?' 15 mins to Downtown, O’Hare airport, West Loop. 20 mins to Lakeview, Wrigleyville, Boystown, Logan Square, Bucktown & Wicker Park.

A spacious modern family room features a large sectional sofa adorned with decorative pillows. A 76” smart TV is mounted on the wall, displaying a beach scene. Natural light enters through multiple windows, illuminating the open layout that flows into a dining area with sleek furniture.

Condo in East Pilsen

4.94 out of 5 average rating, 131 reviews

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Luxury 4BR/2.5BA residence featuring 3 private bedrooms and an open-concept bonus room with a queen bed and full-size bunk beds—perfect for upscale families or executive groups. The spa-inspired primary suite offers a soaking tub and rain shower with multiple settings. Enjoy a modern kitchen, stylish living room with a 76” smart TV, and a large covered patio. Located near UIC, West Loop, Chinatown, McCormick Place, the lakefront, and some of Chicago’s best dining and cultural attractions.

Top guest favorite

A welcoming living area features a dark sofa accented with textured pillows, positioned near a decorative fireplace. Natural light enters through the large window, which overlooks greenery outside. A mirror and decorative elements enhance the space, creating an inviting atmosphere.

Apartment in Little Italy

4.99 out of 5 average rating, 277 reviews

Modern+Spacious Inn Little Italy Near W Loop W/PKG

Welcome to our super clean and thoughtfully designed 4 bedroom 2 bath first floor apartment located in the heart of Chicago’s Little Italy, in close proximity to Downtown Chicago ( two miles), West Loop, Greek Town, The Medical District and University of Illinois at Chicago Campuses. You will have no trouble reaching the hottest destinations in Chicago via foot, bike, Uber, cab, or train. Come be our guest! Please read our full listing description and house rules prior to booking.

A spacious living area features a large sectional couch, adorned with decorative pillows. A sleek coffee table sits in front, and a framed cityscape photograph hangs on the wall. Natural light illuminates the space through three windows, enhancing the welcoming atmosphere.

Home in Roscoe Village

4.92 out of 5 average rating, 294 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

Upgraded luxury 2000 sqf living in this beautiful walkable, desired and safe Roscoe Village/Wrigleyfield, surrounded by shops+restaurants. 5min walk to Brownline Paulina station, Divvy Bike rental; 20min walk to WrigleyField, 3 miles to beaches/Lake Michigan, 5 miles to downtown Chicago; fast WiFi, a dedicated office room with a 22" monitor for your work hours; smart 65" TV in the Living room, smart 50'TV in Master bedroom, walk-out deck. Chef's kitchen, complimentary premium coffee

A modern living area showcases a coffered ceiling and stylish furnishings. Plush sofas and accent chairs are arranged around a coffee table, with a large wall-mounted television and a decorative painting enhancing the aesthetic. Natural light enters through multiple windows, illuminating the space.

Condo in West Town

4.98 out of 5 average rating, 169 reviews

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

A cozy living area features comfortable seating with a dark blue sofa, two armchairs, and a wooden coffee table. Natural light streams through large windows adorned with decorative frames. A small decorative tree and artwork add warmth to the space, complemented by a soft area rug.

Home in Old Town Triangle

4.85 out of 5 average rating, 174 reviews

Historic Old Town, Fabulous 4 Bedroom Home

Lovely Historic 4 Bedroom, 3 bathroom home in Old Town, walking distance of restaurants, boutiques, coffee shops, the lake front and excellent public transportation. 2nd Fl. Master Bedroom has a King size bed and Twin plus private bath with bathtub, walk in shower, w/d; 2nd Fl. two room "suite" with a Queen size bed in each room and private bathroom. 1st Fl. bedroom with Queen bed and private bathroom. Off Street Parking and Private Deck! License Pending.

The living area features a stylish yellow sofa paired with two accent chairs. A round coffee table sits on a soft area rug, while large windows are dressed with sheer curtains, allowing natural light to fill the space. A decorative plant adds a touch of greenery.

Home in Avondale

4.85 out of 5 average rating, 126 reviews

The Logandale: HUGE Mid-Century Home, sleeps 15

Welcome to The Logandale! This 4 bed/3 bath mid-century modern home is ideal for families, professionals, and groups. Enjoy an open floor plan, private patio, game room, and bedrooms with memory foam mattresses. The fully-equipped kitchen, Smart TVs with Netflix, and a backyard fire pit ensure a comfortable stay. Located in the trendy Avondale/Logan Square, you're close to public transport, eateries, and attractions. Experience Chicago's best with us! 🌃🛏️🎮🔥

An open concept living and dining area features a blue sectional sofa paired with a round coffee table on a patterned rug. A sleek TV stand displays a scenic image. A dining table with black chairs and a chandelier is visible in the background, enhancing the space.

Home in Brookfield

4.89 out of 5 average rating, 106 reviews

The Brookfield Breakaway w/ Game Room

This stylish place to stay is perfect for group trips. This split level home has an open concept living room and dining room combo. The gorgeous kitchen has exceptional attention to detail. There are three bedrooms and one bathroom upstairs. Downstairs you’ll find a master suite equipped with its own living space and en suite bathroom. Relax outside on our sectional and enjoy BBQ time with your loved ones. There’s enough space for everyone to enjoy.

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Popular amenities for Chicago mansion rentals

Free parking on premises

Air conditioning

Mansion rentals with a pool

A spacious living area is characterized by a plush gray sofa and a round coffee table. Decorative wall elements and a vibrant red holiday tree enhance the modern decor. Soft lighting is provided by a statement chandelier hanging from the ceiling.

Home in Glen Ellyn

4.76 out of 5 average rating, 17 reviews

Pardizes Suites

A spacious living room is featured with a cream-colored sectional couch facing a mounted flat-screen TV. Natural light pours in through large windows adorned with blinds. A stone accent wall adds texture, complemented by two decorative pieces and a ceiling fan.

Home in Munster

5 out of 5 average rating, 11 reviews

Munster hide away

A single-story house is set against a backdrop of trees, featuring a stone facade and a sloped roof. A winding driveway leads to a two-car garage on the right. Lush green grass surrounds the home, contributing to a serene environment.

Home in Lockport

4.56 out of 5 average rating, 16 reviews

Hidden GEM OASIS in Chicagoland with inground POOL

A sunny backyard features a round in-ground pool surrounded by lush green grass and vibrant flower pots. The house showcases a two-story design with a balcony and large windows, providing views of the serene outdoor space and nearby landscaping.

Home in Des Plaines

5 out of 5 average rating, 5 reviews

Rosemont 4BD2BA house with Pool

Top guest favorite

A spacious basement game area features a classic pool table with a vibrant green felt surface, complemented by cues and an arranged set of colored balls. Nearby, a seating area with leather couches and an arcade machine is visible along the wooden-paneled wall.

Home in Bloomingdale

4.93 out of 5 average rating, 55 reviews

Now Open: Heated Pool with Entire House

A modern living room features a vibrant orange sofa with two decorative pillows, accompanied by a green armchair. A glass coffee table holds a wooden tray and a decorative item. Large windows allow natural light to fill the space, revealing an urban view.

Apartment in Chicago Loop

4.5 out of 5 average rating, 4 reviews

Two Units: Seamless Stay, Downtown Convenience

Apartment in Chicago Loop

4.64 out of 5 average rating, 64 reviews

Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12

An aerial view captures a landscaped amenity yard featuring an indoor hot tub house and multiple lounge seating areas. A mix of patio furniture in shades of blue is arranged over green grass. The outdoor space is surrounded by trees and includes access to the rear deck.

Apartment in Humboldt Park

4.93 out of 5 average rating, 15 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

Luxury mansion rentals

A spacious living area is featured, showcasing a modern sectional sofa adorned with cushions. A wooden coffee table sits centrally, accompanied by decorative items. The open layout includes a dining area with circular chairs and a large window allowing natural light to fill the room.

Condo in Uptown

5 out of 5 average rating, 5 reviews

Ultra Modern Luxury - New Construction 4 Bedrooms

The exterior of a historic brick home features a prominent gable roof and leaded windows. Lush greenery surrounds the property, highlighted by manicured shrubs and trees. A pathway leads to a welcoming entrance, inviting guests to explore the beautiful architecture of the residence.

Home in Hyde Park

5 out of 5 average rating, 19 reviews

Amazing historic campus mansion!

A modern living area features a curved sofa and two armchairs, arranged around a circular, striped rug. A flat-screen TV is mounted on the wall above a sleek fireplace. Natural light enters through large windows, complementing a dining area with a round table and multiple chairs.

Home in Chicago

4.89 out of 5 average rating, 53 reviews

CasaNova Modern City Living

A stylish living room features a glass coffee table atop a textured rug, surrounded by two orange, velvet armchairs and a plush, patterned sofa. A decorative fireplace is framed by elegant vases, with a mirror reflecting natural light from the windows.

Home in Wicker Park

4.98 out of 5 average rating, 159 reviews

Spacious Five Bedroom Home in Trendy Chicago Neighborhood

An expansive rooftop patio is showcased, featuring woven outdoor couches with blue cushions arranged around a glass-top table. The city skyline is prominently visible, with notable buildings punctuating the clear blue sky, complemented by touches of lush greenery.

Home in Near North Side

4.98 out of 5 average rating, 62 reviews

Private Downtown Retreat with Rooftop Oasis

The living area features high ceilings and large windows, allowing natural light to illuminate the space. A cozy sectional sofa is positioned around a coffee table, while a wall-mounted television hangs above a modern fireplace. Soft blue carpeting adds warmth to the decor.

Home in Wrigleyville

4.91 out of 5 average rating, 185 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

A comfortable living room is showcased with a grey sofa adorned with decorative pillows. A round coffee table sits on a patterned rug, and a green vintage cabinet adds a pop of color. Bright light enters through open doorways, leading to a dining area beyond.

Condo in Lincoln Park

4.96 out of 5 average rating, 109 reviews

Large Remodeled Home in Lincoln Park, Sleeps 12!

A bright living area showcases light hardwood floors and high ceilings. Elegant furniture pieces include two soft blue armchairs and a pale upholstered sofa. A round coffee table is centered on a patterned area rug, complemented by greenery from potted plants and natural light filtering through large windows.

Home in North Side

5 out of 5 average rating, 54 reviews

Lux LoganHouse w/garage, Sleeps 12, & rooftop deck

Pet-friendly mansion rentals

A spacious living area features a large sectional sofa adorned with colorful cushions. A round coffee table sits in the center, complementing a light area rug with intricate patterns. Natural light fills the room through a window dressed with soft curtains, creating a welcoming atmosphere.

Home in Evanston

4.95 out of 5 average rating, 43 reviews

Grey House: 4 Bdrm 2 Bath Bunglow with skylights

The exterior of a historic building showcases large glass windows framed by green trim. Natural light streams into the space, illuminating various items displayed inside. The backdrop features a view of a nearby architectural structure, adding visual interest to the streetscape.

Condo in Chicago

4.96 out of 5 average rating, 97 reviews

Private Lincoln Park Condo with 2 Parking Spots

A bright and inviting living room features a comfortable sofa adorned with patterned cushions. A soft throw is draped over an ottoman. Natural light filters through a large window, and a 'WELCOME' sign is displayed on the wall, enhancing the space's approachable atmosphere.

Home in Elmhurst

4.93 out of 5 average rating, 165 reviews

The Ultimate Escape|Unpack|Relax|Enjoy!Sleeps10-14

A cozy seating area features two brown leather chairs positioned near a contemporary electric fireplace. The wall is adorned with a large painting and a mural resembling a library, creating an inviting atmosphere. Warm lighting enhances the elegance of the space.

Home in Lake View

4.88 out of 5 average rating, 32 reviews

The Grand Vic: Large 5BD/3BA Home (+Garage)

A modern, renovated home is showcased with bright white brick and large windows. A neatly maintained lawn and driveway lead to the home, complemented by soft outdoor lighting. A garage with a wooden door is visible in the background, enhancing the home's curb appeal.

4.95 out of 5 average rating, 59 reviews

Culinary DREAM - Pizza Oven/BBQ/Smoker

A fully equipped kitchen features modern appliances, including a stainless steel refrigerator and microwave. A large island with two metal stools offers additional seating. Natural light streams in through the window near the sink, illuminating the sleek countertops and cabinetry.

Apartment in Humboldt Park

4.85 out of 5 average rating, 161 reviews

*Comfortable & Spacious Home Close to Downtown*

An inviting dining area features a large wooden table surrounded by white chairs. A circular mirror adorns the wall, while natural light fills the space, highlighting large plants positioned throughout. A small side table displays a vase with sunflowers, adding a touch of greenery.

Apartment in West Town

4.85 out of 5 average rating, 111 reviews

Comfy&Spacious | Close 2 Downtown | Parking +Patio

A modern open-concept living space is showcased, featuring a fully equipped kitchen with an island and bar stools. The dining area is set with elegant table settings. A cozy seating arrangement includes green accent chairs and a wooden table, illuminated by pendant lights.

Home in Arlington Heights

4.95 out of 5 average rating, 37 reviews

Stylish Escape/Game Room/4 Brs

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