Mansion vacation rentals in Chicago

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.)

4BDRM Gorgeous Apt Pilsen Private Prking Available

Stylish Retreat for Groups in Vibrant Pilsen Welcome to our 7-room home in lively Pilsen, perfect for families and groups of up to 10. Enjoy spacious comfort in a prime location. Explore vibrant murals, visit Simone's bar, and savor Sunday brunch at Dusek's. Catch a concert at Thalia Hall or sing at nearby karaoke or grab dim sum. Conveniently located just down the street from Chinatown and close to McCormick Place. Ideal for conventions and city adventures. Book now for an unforgettable stay!

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.

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)

Skyway w/ Shuffleboard

Welcome to our spacious split-level home– an inviting retreat perfect for families, groups of friends, and business travelers. This comfortable haven combines the convenience of a prime location with all the amenities you need for a relaxing stay. Have some fun with family and friends by laying a shuffleboard tournament. Enjoy plenty of room to spread out, fun entertainment, beautiful backyard, plenty of parking, 5 King beds and easy access to Chicago’s attractions via Metra or expressway.

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.

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.

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.

The Chicago Game Room (Oak Park, IL)

There is no other rental like this in the Chicago area! Located in the first suburb west of Chicago, this 4-bedroom, two-level private apartment is brand new and ready for your group to enjoy. It features an amazing game room/living room with cathedral ceilings, skylights, gas fireplace, bar seating, pool table, shuffleboard/bowling table, dart board, four bedrooms + sleeper sofa, full kitchen, spa-like bathrooms, in-unit washer/dryer, and private deck. GUESTS = 8 MAX