Mansion vacation rentals in Chicago

Stunning Old Town Penthouse with Private Rooftop

This listing is for the entire building, which is the combination of a penthouse loft (3BR) and the unit directly underneath (2BR), easily connected by private stairs. You will also have a private rooftop deck. This is a beautiful 4,000 sq. ft penthouse loft combined in the heart of downtown Chicago. The building is next to "Magnificent Mile" and steps away from amazing restaurants, comedy clubs (Zannies, Second City), theaters, boutique shopping, public transportation (red line, and 156 bus line), bars and just four blocks from the beach. **Please be aware there are 45 steps to get into the unit (2 flights). This building is truly one of a kind. Built in 1897 and completely renovated in 2016 this unit has exposed brick, 20 foot ceilings and 120 year old barn wood floors capped off with a rooftop deck overlooking Willis (Sears) Tower. 5 bedrooms - 4 with king beds and one with 3 single beds (a bunk bed and a separate single) Also a nook area with a twin bed, built in reclaimed wood; very cute, unique, and comfortable sleeping area! 4 full bathrooms Two full kitchens and two full living rooms. Penthouse master bedroom- Fit for a king. Located on balcony level overlooking living room. Vintage french doors open to balcony. Furnished with a tempurpedic king sized bed and 50 inch TV. Attached to marble bathroom with jacuzzi and all-marble rain forest dual shower head steam shower. Enjoy Kohler faucets and heated floors. (All assortments of toiletries, blow dryer, extra towels, linens, and extra pillows and blankets included) Penthouse second and third bedrooms - Spacious and comfortable, king bed in one, three singles in one. Nicely outfitted with crown molding and large closets. Second Bathroom - Marble floors, classic European style and granite counter tops. (All assortments of toiletries, blow dryer, extra towels and linens included) Fourth bedroom - Furnished with a cloud like king sized bed, crown molding, exposed brick, and large closet. Remote controlled overhead fan. Connected to a brand new subway tiled bathroom with antiqued brass hardware and a jacuzzi. Enjoy heated floors here as well. (All assortments of toiletries, blow dryer, extra towels, linens, and extra pillows and blankets included) Fifth bedroom - Spacious and comfortable, with cloud like king bed. Crown molding, exposed brick and large closet. Remote controlled overhead fan. Fourth Bathroom - Subway tiled walls with antiqued brass hardware here as well, classic European style marble counter tops. (All assortments of toiletries, blow dryer, extra towels and linens included) Extra amenities include two push button fireplaces, vintage 1950 Valley pool table, dartboard, surround sound stereo system, PS3 (with movies and games), blu ray, board games and two 60-inch hanging TVs both equipped with HBO, Netflix, Showtime, TiVo, and Amazon each in their own full sized living rooms. Two full laundry rooms in building with irons and ironing boards. Last but not least is the private rooftop deck. This view is absolutely magnificent. Your first walk out onto this large spacious rooftop deck will leave you speechless. It boosts a comfortable couch, grill, and large table all adorned with round draping bulb lights going from corner to corner of the deck, with a full 360 degree view of the Chicago skyline. You will never forget your Chicago visit when you are on the roof deck after the sunsets and the city lights fill up the sky. Spoil yourself in the Windy City. There is nothing else like this in the city. Upon arrival, a welcome packet that will explain to you all about the features of the penthouse and how to maximize your time while staying here. Anything from how to work the jacuzzi to how to operate the electronics is outlined and at your disposal when you walk in the door. We are also pet friendly. While exploring the city we are very centrally located we recommend walking or biking to places like Michigan Ave and the Oak Street beach. A wonderful place to spend an afternoon! There is a parking garage across the street for $26/day located at 1225 N Wells Street. There is also metered street parking. Old Town is an historic area of Chicago right in the middle of the action. It's a perfect base from which to experience the city. Walk or bike to interesting places like Michigan Avenue and the Oak Street Beach. We are very close the the Red Line El train and numerous buses and a divvy bike station. Parking garage across the street. Uber and Lyft are choice methods as well. However, being in the heart of Old Town there is plenty within walking distance.

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!

Jacuzzi, King Beds, Easy Access to DT Chicago!

Our 4bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful neighborhood. There is plenty of space for 10 people to sleep comfortably (4 beds), as well as 4 smart TVs (w/ complimentary Hulu & Disney+), a deck w/ a pergola, built-in grill, & firepit, a large fenced backyard, a game room (w/ ping pong and more), a jacuzzi, an office space, & much more. Great access to City of Chicago by I-290, as it's directly west of Downtown!