Mansion vacation rentals in Chicago

Find and book unique mansions on Airbnb

Top-rated mansion rentals in Chicago

Guests agree: these mansions are highly rated for location, cleanliness, and more.

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Guest favorite

A welcoming porch features a wooden deck with white railings and columns. Two chairs are positioned on the porch, accompanied by a barbecue grill nearby. Lush greenery is present, enhancing the outdoor space's natural appeal.

Home in Hyde Park

5 out of 5 average rating, 16 reviews

Amazing historic campus mansion!

This stylish campus mini mansion is perfect for group trips in the historic Hyde Park neighborhood. A cheerful, modern renovation of a historic home, with original woodwork, underfloor bathroom heating and leaded windows. Easy access to Uchicago, the lakefront, Chicago marathon, McCormick trade shows, the Museum of Science & Industry or exploring our vibrant city. Our spotlessly clean property helps you experience everything Chicago has to offer. Hosted by a very experienced all 5 star host.

Guest favorite

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 Lake View

4.92 out of 5 average rating, 227 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.

Superhost

A bright and open dining area features a wooden table surrounded by multiple white chairs. Large windows allow natural light to fill the space, highlighting a modern living room setup with a green sofa and a decorative plant.

Condo in Lincoln Park

4.8 out of 5 average rating, 160 reviews

Massive Old Town Home Steps to Wells St & Beach

Start your Windy City adventures in my spacious 3rd-floor duplex in the heart of Chicago's vibrant Old Town neighborhood! This 8 bed, 4 bath home comfortably sleeps up to 20 guests, making it perfect for large groups or families. Enjoy modern furnishings, a fully equipped kitchen and two cozy living areas to relax in after exploring the city. Steps from popular restaurants, bars, boutiques and the lake, you’ll be immersed in local charm. (Please note, parties and large events are not allowed)

Superhost

A cozy seating area is highlighted by two comfortable armchairs, one adorned with a decorative pillow. A coffee table sits centered, decorated with a small plant and decorative trays. Light drapes frame the windows, enhancing the warm atmosphere created by wooden flooring.

Apartment in Hermosa

4.77 out of 5 average rating, 13 reviews

2Level Duplex + Jaccuzi! Gem in Chicago 4BD/3BA

Welcome to our stunning getaway! This luxury duplex is designed to provide comfort & entertainment for your group of up to 8 guests; Indulge in the spacious entertainment area. The backyard is your private oasis, a beautifully landscaped space perfect for gatherings. With 4 lavish bedrooms, a fully equipped kitchen, & modern amenities throughout, your stay here promises both luxury and convenience. Our central location puts you just moments away from the city's finest attractions. Book now!

Guest favorite

Home in West Town

4.94 out of 5 average rating, 34 reviews

Huge Restored Humboldt Park Mansion - Park Views!

Located directly across the street from the huge and gorgeous 200 acre Humboldt Park. This recently restored mansion is an amazing place to bring the whole family with lots of room for gathering together. 5 bedrooms and 3.5 bathrooms ensures that there is plenty of space for all and with a massive public park across the street you can stroll through the park, take a swan boat out on the pond or join a game of soccer or basketball. Easy public transportation and plentiful ubers.

Top guest favorite

A modern kitchen featuring a large island with seating for six, complemented by sleek cabinetry and stainless steel appliances. Natural light fills the space through a nearby window, and an adjacent dining area is visible, offering a blend of functionality and style.

Home in Avondale

5 out of 5 average rating, 11 reviews

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Superhost

A bright living space features a sectional couch positioned around a glass coffee table. Large skylights and windows allow natural light to fill the room, which is accented by a decorative rug and a modern electric fireplace. A television hangs on one wall, displaying a scenic landscape.

Apartment in Logan Square

4.92 out of 5 average rating, 12 reviews

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

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

Guest favorite

A private deck is highlighted by comfortable seating arrangements, surrounded by soft string lights that provide a warm glow. A patterned rug lies beneath the furniture, creating an inviting space for relaxation. Nearby, a potted plant adds a touch of greenery to the outdoor area.

Home in Lincoln Park

4.85 out of 5 average rating, 167 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.

Top guest favorite

A putting green mat is positioned against a tropical-themed mural featuring palm trees and a serene beach. Several golf clubs and three orange practice balls are arranged alongside the mat, creating an inviting space for leisure activities.

Home in Elmhurst

5 out of 5 average rating, 45 reviews

Big Family Home with 4 King Beds

Experience ultimate luxury at our exclusive property. Nestled in a prime location, this meticulously designed retreat offers opulent furnishings, panoramic views, and bespoke amenities. Ideal for discerning travelers and work travelers seeking sophistication and comfort, indulge in a private sanctuary where every detail exceeds expectations. Discover the epitome of elegance with us and create unforgettable memories in this exquisite haven.

Guest favorite

Home in Justice

4.93 out of 5 average rating, 224 reviews

3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin

3 Kings | 1 Queen | 1 Full | 3 air beds | 2 Pack 'n Plays No charge for: cleaning, extra people, or any other hidden fees. 20% weekly discount applied to 7+ nights. 20% monthly discount. Less than 5 mins to I-294, I-55. 30 mins to Chicago & O'Hare Airport. 15 mins to Midway Airport. 5 mins to Cook County’s forest preserves w/ bike, walking, and horse trails.

Guest favorite

A spacious living area features comfortable leather seating and a modern fan overhead. A sleek entertainment center with a wall-mounted screen is complemented by ambient lighting. Large windows are adorned with deep blue curtains, allowing natural light to filter in, while decorative plants add a touch of greenery.

Apartment in South Shore

5 out of 5 average rating, 17 reviews

Lux 4BR Lakeshore: W/Rftop Book Now!

Indulge in luxury with a 4-bed, 3-bath short-term stay. Enjoy spacious living, serene bedrooms, and elegant bathrooms. Private rooftop oasis for coffee, work functions, or enjoying the night sky. Near Obama Library, immerse in culture, history, golf, and boat outings. Book now for upscale urban living and relaxation in a dynamic locale.

Guest favorite

Home in Wicker Park

4.89 out of 5 average rating, 57 reviews

Luxury Retreat with Home Theater

Welcome to @TheDreamRentals opulent 5-bedroom sanctuary, where luxury meets entertainment in the heart of the city! Nestled in an upscale neighborhood, this exquisite home boasts not only a full-fledged theater but also two stunning rooftop patio decks, making it the perfect choice for your upscale getaway.