Mansion vacation rentals in Chicago

Spacious Five Bedroom Home in Trendy Chicago Neighborhood

Unwind on the private rooftop deck, soak in the luxurious jacuzzi tub or take a relaxing steam shower after you host a dinner party in your own spacious dining room. Then watch a movie in the entertainment center with popcorn machine and 75 inch TV. Bedrooms are as follows: Master - king 2nd - twin and crib 3rd- queen 4th - twin over full bunk 5th - king and twin over twin bunk We also have a large, U shaped, 40 inch deep Cloud sectional from RH that can sleep 2-3 and 2 air mattresses. Stunning newly renovated home in a fantastic Wicker Park Location! Wicker Park is the Brooklyn of Chicago with tons of unique shops, restaurants full of character and innovative bars. The entire home is yours, giving you rarely found complete privacy in the middle of the city for you, your family, friends and colleagues to enjoy! Expertly designed with gourmet kitchen and multiple living rooms, your party will have plenty of room to spread out during your stay in the Windy City. Utilizing the finest materials & craftsmanship available, some of the premium features include: hardwood flooring on entire 1st and 2nd levels, 10' ceilings, beautiful moldings, sensational gourmet kitchen with large center island, premium stainless appliances and quartz counters, extra-large bedrooms including luxurious master suite with lavish marble baths, steam shower and expansive walk-in closet. Five full bedrooms and 4 bathrooms. The master bedroom has a King bed and very large ensuite bathroom. Bedroom 2 has a twin bed and a crib (upon request), bedroom 3 has a queen bed and a daybed. Bedrooms 2 and 3 share a hall bath. Bedroom 4 has bunk beds and bedroom 5 has a king bed and a daybed. Bedrooms 4 and 5 share a bathroom. The basement has a large entertainment area with a wine fridge, popcorn machine and 75 inch TV. **For those with infants and toddlers, in addition to a crib, we also have a SNOO bassinet and a Bugaboo cameleon stroller for your use. **If you would like to use any of these, please specify in your booking so that we can have them out and available to you. Otherwise, we keep them out of the way for guests who are not needing them. If you need parking please let me know in advance ** We have keyless entry for super easy check in. I am always available by phone, texting is best, but we want you to have the most convenience possible. That’s why we have keyless entry for seamless check in. No hassle for late arrivals, etc. Simply type in the code provided after confirmation and you’re all set! The neighborhood is the most buzzed about in Chicago, with trendy restaurants, shops, and bars within an easy walk, not to mention the beautiful park. Blue line is only a few blocks, which gives direct access to O'Hare International Airport. Uber and Lyft are always minutes away, and a Divvy bike station is right around the block. Chicago is a great city to explore. We are in the living breathing heart where locals reside so you’ll get the best the city has to offer!

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!

Entire house, close to O'Hare airport

You and your family will be close to all amenities when you stay at this centrally-located place. 5 miles from O'hare Airport, 1.3 miles from Allstate Arena, 4 miles from Rosemont Convention Center and 5 miles from Fashion Outlet of Chicago. Few mins from Rivers Casino, Shopping Centers, Restaurants, Express way. Easy access to I-90 & I-294. 15 miles away from Chicago Downtown. A newly renovated space with extremely fast WIFI up to 800mbps, suitable for WFH. Walking distance to a close by lake.

Andersonville Home for Groups! Hot Tub Yard Garage

Bring the whole family to this great place with lots of room. Two floors have 4 bedrooms, 2 bathrooms, 6 beds and tons of room to watch movies, play ping pong, and have a meal together. You literally cannot get closer to Andersonville center, and it’s a great home base to be not far from the lake, and Wrigleyville. The enormous back yard has a hot tub, fire table, and tons of room for games, kids, and dogs. We do have a strict quiet hours policy and backyard access is prohibited after 10pm.

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!

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)

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Say "WOW" in this top floor, DRAMATIC SPACIOUS Loft condo w/ PRIVATE ROOFTOP overlooking skyline! 45 seconds to Wrigley! Open 2-story layout w/7 individual bed options, 3 full bathrooms, fully-stocked kitchen + huge island. Enjoy luxury flooring, soaring high ceilings, keyless entry, 2 HD TVs, & brand new BBQ grill. Perfect for special occasions! Next to Wrigleyville bars & restaurants. Train to Downtown only 12 mins. Up to 4 parking spaces for rent. Over 1300 5-star reviews across listings!

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.

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

This will likely be the largest condo you have ever seen. This condo is 5 mins from the University of Chicago and the University of Chicago hospital. You will be a quick 10-15 min uber ride from downtown and 5 mins from beautiful Lake Michigan. We are currently only booking out of town travelers. We are not doing parties or events. I live in the building so if you are trying to have a party I will have it shut down and you will be asked to leave within an hour.

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! 🌃🛏️🎮🔥

Beautiful Chicago Greystone

Spacious, private, 4 bedroom condo 15 minutes directly west of the city center. Minutes away from the West Loop, Garfield Conservatory, Downtown, and United Center. Ideal public transportation access with multiple bus stops within 1 block radius, 2 blocks away from Blue Line CTA, 1 mile away from Pink Line CTA. Exquisite back porch and patio with access to grill and patio furniture. Onsite laundry per request Local hosts!

Great group stay - 10 adults 4 bdrm w workout area

Duplex down of building that sleeps 10 adults 2 children on rollaways*, 3 bathrooms, 2 king bedrooms and 2 queen bedrooms and 1 additional queen bed in the open basement family room tucked away in the corner, bring the entire family or friends for time in Chicago, we now have added a Peleton and a Concept 2 rower. * if you need the 2 rollaways you’ll need to let me know 24 hours before checkin.