Mansion holiday rentals in Chicago

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Top-rated mansion rentals in Chicago

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Top Guest favourite
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
4.97 out of 5 average rating, 126 reviews

Private Lincoln Park Condo with 2 Parking Spots

Built in 1895 and updated in 2025, the condo provides historic charm with modern convenience. The unit is light filled with ample space to spread out and relax. The bathroom has been fully remodeled and the kitchen is updated. The unit has a private balcony deck and a landscaped common patio. The unit includes 2 free off-street parking spots. Amenities include 60" 4K Smart TV, fiber internet, Nest Thermostat & Tuft & Needle/ Casper mattresses. Enjoy living in the heart of Lincoln Park.

Top Guest favourite
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, 186 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!

Guest favourite
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
4.97 out of 5 average rating, 128 reviews

Large Remodeled Home in Lincoln Park, Sleeps 12!

Stay in this thoughtfully remodeled home in Lincoln Park. Sleeps 12 w/ complimentary access to 3 parking spots! Enjoy the spacious layout, massive bedrooms, 2 private decks, and front yard w/ a grill. You will be steps from the North & Clybourn Red Line station, Divvy stations, Binny's, Whole Foods, Trader Joe's, Steppenwolf Theatre, so many incredible restaurants! Our home is (conveniently!) located next to train tracks. If you are a light sleeper, this urban location might not be for you.

Guest favourite
A spacious living area features a light blue couch with patterned pillows, paired with a cream armchair. Light wood floors extend throughout, creating a warm ambiance. A dining area is visible in the background, highlighted by a chandelier and a decorative wall with exposed brick.
Townhouse in Logan Square
4.86 out of 5 average rating, 286 reviews

Live Logan Square The Globally Loved Neighborhood

Discover your serene Logan Square oasis on a quiet cul-de-sac, just steps from Milwaukee Ave’s top restaurants, bars, Maplewood Brewery, Stan Mansion, Rosa’s Blues Lounge & The Whale. Explore the 606 Trail, hop the Blue Line to airports & downtown, Fullerton bus to Lincoln Park Zoo, and Lakefront or stroll to Bucktown, Wicker Park & the public library a block away. Enjoy self-check-in, free street parking, a fully equipped kitchen, 4 BR, 2 BA, washer/dryer & yard. (No parties per Chicago regs.)

Superhost
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 Magnificent Mile
4.82 out of 5 average rating, 238 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!

Guest favourite
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
4.93 out of 5 average rating, 137 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 favourite
An outdoor terrace features comfortable lounge seating and a grill. A panoramic view of the Chicago skyline is visible, showcasing various architectural styles and buildings under a clear blue sky.
Townhouse in Fulton Market
4.99 out of 5 average rating, 275 reviews

Spacious 4-Level/4-Bedroom Townhouse in West Loop

Spacious Townhouse in Chicago's Hip Foodie Neighborhood: West Loop/Fulton Market. This is a Private, 4-Story Townhouse on a Tree-Lined Street just Steps from the Action...while still quiet enough for a good night's sleep. Walk to some of the Nation's Top Restaurants (near Restaurant Row), Clubs, Pubs, Groceries, Parks, Coffee Shops. Easy Train Transit to O'Hare, Navy Pier, Mag Mile, McCormick Place, etc...Terrace w/Skyline Views & Attached Garage Parking for 1 Regular-Sized Vehicle Included!

Top Guest favourite
The kitchen is equipped with cherry cabinets and granite countertops, featuring modern appliances such as a Subzero refrigerator and Wolf gas stove. An island with counter seating is surrounded by black stools, creating a space for socializing while meals are prepared.
Home in Ranch Triangle
4.95 out of 5 average rating, 126 reviews

Stunning Home, Awesome Game Room, A+ Location

Looking for a place for your group to gather together? This single-family home is perfect and private! Whip up meals in the chef’s kitchen, featuring a Subzero refrigerator and Wolf stove. Island seating allows everyone to socialize while prepping meals and drinks. You might not ever leave with a game room featuring pool, ping pong, foosball, two classic arcade machines and an Xbox - but if you do the location is perfect with easy walking to two L stops and tons of shops and restaurants.

Top Guest favourite
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, 313 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.

Guest favourite
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
4.97 out of 5 average rating, 201 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.

Top Guest favourite
A cozy living room features a warm fireplace with a flat-screen TV mounted above. Comfortable leather chairs and a plush sofa surround a coffee table, while large windows allow natural light to fill the space. Potted plants add a touch of greenery.
Bungalow in Lake View
4.95 out of 5 average rating, 153 reviews

Chicago Bootlegger House Sleeps 10-20

Walk to restaurants, groceries, shopping, Wrigley Field, Lake Michigan, Beaches, Boat Harbor, Lincoln Park Zoo, night life, bars, clubs, Red Line Train, Lakeshore Drive and more; all just a few blocks from your door. Giant house on 2 levels with over 3,500 square feet of living space and 6 bedrooms. Nicely decorated and lots of places to sit and mingle or watch one of the 85" TVs. Private 2 spot parking in garage and a parking pad for oversized vehicles.

Guest favourite
An open and airy living space is highlighted by high ceilings and vibrant red beams. Large windows allow natural light to fill the room, complemented by palm tree decor and ceiling fans. The minimalist furniture invites relaxation in a colorful and modern setting.
Home in Wicker Park
4.9 out of 5 average rating, 212 reviews

ALOHA Tropical Penthouse in Wicker Park Sleeps 14

Follow @bangtel for perks and deals! Look no further for your vibrant city escape! Welcome to your tropical penthouse paradise, ALOHA — a 2,000 sq ft oasis in the ❤️ of Wicker Park. This modern, design-forward retreat blends Hawaiian vibes with bold color, playful energy, and luxurious comfort. Just steps away, discover Wicker Park’s best restaurants, boutiques, nightlife, and parks — the ultimate blend of urban excitement and laid-back luxury.

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