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Vacation Homes for Sale in Chicago, IL
52 homes
New
474 N Lake Shore Dr Unit 4808, Chicago, IL 60611
Amazing views offered at this bright and beautiful, turn-key condo in one of Streeterville's most premier locations! As you step inside your corner unit, you are greeted by jaw dropping / unobstructe...
New
127 W Maple St Unit 2, Chicago, IL 60610
CASH INVESTOR ONLY. Tenant's lease 2400/month until June 2025. Huge & bright one bedroom plus a bonus room in prime Gold Coast location! Very large living room/dining room with 10' ceilings and hardw...
New
3231 N Octavia Ave, Chicago, IL 60634
This stunning, modern-chic home, set on a wide lot, offers a "wow" factor at every turn. Available as a furnished option, it's move-in ready for Airbnb or as your personal retreat. (Listing price exc...
1041 W Glenlake Ave Unit 1, Chicago, IL 60660
Beautiful courtyard views in rehabbed central air conditioned 2 bedroom 1.1 baths on first floor with open floor plan. Great for entertaining. Hardwood floors thru out with good closet space. High ce...
New
711 W Buckingham Pl Unit 1W, Chicago, IL 60657
Look no Further, this is The One! Extraordinary, Impressive & Outstanding is what comes to mind with this Luxurious East Lakeview Condo! This extra wide pristine Luxury duplex down (3) Bedroom (2.5) ...
New
1504 W Greenleaf Ave Unit 1, Chicago, IL 60626
Bright, sunlit 1-bed, 1-bath condo with an estimated 800 square feet of vintage charm! This well-designed layout includes a spacious living room, formal dining room, and kitchen, all with beautiful n...
1520 N Hudson Ave Unit 4, Chicago, IL 60610
Stunning Penthouse home with private rooftop deck and garage parking with EV Outlet. Located on a quiet tree-lined street in the heart of Old Town! Enter to a sunlit, open floor plan highlighted by c...
13402 S Avenue N, Chicago, IL 60633
Welcome to this charming and meticulously-maintained all brick home located in Chicago's Hegewisch neighborhood. This 2-bedroom, 2-bathroom home features a bright and spacious and open layout, ideal ...
10820 S Eggleston Ave, Chicago, IL 60628
Make your holiday truly special with a brand new home!! Located in a highly popular and sought after area, this Bungalow has been completely rehabbed and awaits you and your family. Upon entry the co...
880 N Lake Shore Dr Unit 12GH, Chicago, IL 60611
Welcome to the opportunity to live in the iconic Mies van Der Rohe 880 N Lake Shore Drive building towering over a prominent Streeterville location with some of the best views of Chicago's skyline an...
3536 N Ashland Ave Unit 2N, Chicago, IL 60657
In a beautiful elevator building and overlooking the tree tops, this gorgeous city home is ideally located in the heart of Lakeview and features a PRIVATE 2.5 CAR GARAGE. Large east facing windows fl...
680 N Lake Shore Dr Unit 1316, Chicago, IL 60611
680 is one of the most iconic and expansive buildings in the city, taking up one entire city block. The main level features large open hallways and tall cathedral ceilings. The door staff are an adde...
5905 W Erie St, Chicago, IL 60644
Welcome to 5905 W. Erie! Like new construction this home has been completely renovated from the roof down, home has new roof, plumbing, electrical, HVAC, sewer and water service. As you enter this la...
Price drop
8623 S Prairie Ave, Chicago, IL 60619
Experience the allure and elegance of this stunning home at 8623 S Prairie Ave, set in the esteemed Chatham neighborhood of Chicago. With its seamless fusion of timeless architectural charm and conte...
Price drop
474 N Lake Shore Dr Unit 4705, Chicago, IL 60611
Breathtaking Views & Modern Living in the City Next to Navy Pier! This stunning High Floor Corner 2-bedroom / 2 Bathroom desired 05 model home on Lake Shore Drive offers incredible North & East views...
3344 N Kildare Ave, Chicago, IL 60641
Don't miss this huge gem Pride of ownership shows throughout. This two story home also offers a deck off master suite a cozy porch off kitchen , beautiful honey color wood floors and a garden l...
1030 N State St Unit 38GH, Chicago, IL 60610
Welcome to the crown jewel of Newberry Plaza - an exquisitely renovated large 2-bedroom, 2-bathroom + office/den residence that redefines luxury living in the Gold Coast. Every inch of this home has ...
9807 S Longwood Dr, Chicago, IL 60643
Welcome home to 9807 S Longwood Drive, a pristine and meticulously maintained oversized Bungalow in the heart of the charming and historic Beverly neighborhood. Nestled on Longwood Drive, one of Beve...
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