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Classic Elegant Home posh Roscoe Village & Wrigley

Spacious elegant first floor flat. Very high speed internet for work. One block from top dining + shopping. Easy walk to Wrigley Field. Bose music & Smart TV. Very well equipped & stylish with great Zen. Chefs kitchen, marble steam bath & even stained glass. Well stocked pantry + dining space to entertain. Take the bus or train downtown or wine & dine close by. Experience a true feel of a classic Chicago upscale posh Victorian home. Also Month to Month Affordable Posh Vacation Chicago Home

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)

Romantic Gastro Loft Retreat for Two

Located above the area’s hottest new restaurant, this newly renovated 1BR/1BA urban loft features classic finishes - exposed brick, high ceilings, maple floors, and quartz countertops. Cozy, comfortable quarters directly above the Houndstooth restaurant provide a fantastic opportunity to get a “taste” of the Benton Harbor Arts District. Muffled sounds of music and activity from the restaurant below are often present in the loft during evening hours. Some guests may find this objectionable.

Peaceful & Private Hot Tub Vacation Home Getaway

A Rare gem 💎in the heart of Homewood. This Quaint 2-bedroom remodeled home is charming, sophisticated and discrete. It is minutes away from the Metra station, golf course and downtown Homewood shops. The energy is very calm and quiet ☯️. This is the home away from home where details are everything and the pictures do not capture the essence of this luxurious space. Experience the love, the joy and the peace that continues to leave its mark. Peace and Love - Michael and KP💞

Stunning Retro Apartment in Andersonville

Stay in this perfectly situated apartment in the heart of vibrant Andersonville and find out why TimeOut Magazine calls this “The Coolest Neighborhood in the US”. Full of natural light, this 2 bedroom, 1 bath home has generous room sizes, and located on the ground floor of an immaculately kept vintage 4 unit building that has been fully upgraded with modern amenities. Plenty of free parking 24/7. Folks who stay here really will get an authentic Chicago-style experience.

Beachside Bungalow 1-bedroom with On-site Laundry

Conveniently located 2 miles from beautiful Weko Beach and 4 miles from Warren Dunes State Park. This rental features a full kitchen, cozy living space with sleeper sofa, queen size bed in the master bedroom and a spacious bathroom that includes a washer and dryer on site. Charming enclosed porch offers an inviting space for your morning coffee before heading out to the beach for the day. Private parking included. This unit is on the second level accessible by stairs only.

~Exquisite 2-BR Residence| Top Notch Amenities ~

Welcome to our Chic 2-Bedroom Haven in Ukrainian Village, Chicago! This stunning modern unit offers high-end amenities and a true interior designer's dream. Experience the perfect blend of modern convenience and charm at our high touch vacation home. The carefully designed master bedroom comes with its own, amazing, private bathroom. Pets are allowed in unit but not on furniture. $500 fee will apply if hair is found on furniture.

Lively Wicker Park 2br, Steps to Damen Blue Line

Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of amenities. Just a block from everything this neighborhood has to offer and 2 blocks from the 'L' to take you downtown or to O'hare Airport. Premium location to effortlessly walk from our quiet side street and be in the heart of all the entertainment! I provide all the essentials to make your stay easy and comfortable!

Impeccable 5-Bed Wrigleville Beauty

One of a kind absolutely gorgeous 5 bed 2.5 bath duplex down condo inside of an amazingly well-appointed greystone building steps from Wrigley Field. Exposed brick in the living area, incredible kitchen with dual fridges, huge island, and top of the line cabinets/countertops.