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Vacation Homes for Sale in Chicago, IL

40 homes
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3100 N Lake Shore Dr Unit 201, Chicago, IL 60657

Rarely available corner unit. One of the largest floor plans in the building. Welcome to The Darien. Beautifully maintained building with direct access to the lakefront path and parks. 2-Bed/2-Bath ...
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360 E Randolph St Unit 905, Chicago, IL 60601

Desirable NW Corner at The Buckingham can now be yours !! Completely updated from floors to Ceiling, this 2bd/2ba gives you the confidence to know you are in the right place at the right time ! Beaut...
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1211 S Prairie Ave Unit 3906, Chicago, IL 60605

Stunning 3-Bed, 3-Bath Sky-High Condo in the Heart of Chicago. Welcome to 1211 S Prairie Ave. #3906. Renovated in 2017, this 2,200-square-foot, 3-bedroom, 3-bathroom condo with breathtaking views an...
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3730 N Lake Shore Dr Unit 16B, Chicago, IL 60613

LIVE LARGE IN THIS OASIS IN THE SKY. This STUNNING PENTHOUSE unit in this elegant iconic building has phenomenal views from each side: Lake views, City Skyline Views, Wrigley Field and beautiful sun...
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4749 W School St Unit 1E, Chicago, IL 60641

Fantastic 2BR/1BR unit on high 1st floor with covered outdoor deck in well-managed building in Portage Park! Hardwood floors throughout, granite countertops, central air/heat, recessed lighting, wash...
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73 E Elm St Unit 10B, Chicago, IL 60611

Unit now vacant. Gold Coast gem! Looking for one of a kind, historic architecture, non cookie cutter apartment in A+ Goldcoast location on a quiet street just half a block from the perfect Lakefront ...
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6325 N Sheridan Rd Unit 1006, Chicago, IL 60660

Welcome home to your lakefront sanctuary. This unit boasts a sprawling floorplan with giant room sizes and a large walk-in closet. Newer AC units and windows. Conveniently located by Loyola Universit...
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400 E Randolph St Unit 1229, Chicago, IL 60601

Outstanding corner unit with fantastic views from all windows. Hardwood floors throughout, Updated kitchen and baths with top of the line appliances and Granite and quartz countertops. Newer windows....
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211 N Harbor Dr Unit 1007, Chicago, IL 60601

Welcome to your new home at 211 N Harbor Dr., located in New East Side's newest lakefront building, Cirrus Condominiums. This brand-new, 350-unit luxury high-rise condo, completed in March 2022, boas...
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2448 N Normandy Ave, Chicago, IL 60707

Attention builders and developers. Amazing opportunity to bring your vision to build a single family home on this 25 x 125 residential lot located in Montclare. Zoned RS-3.Tear down single family hom...
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800 N Michigan Ave Unit 2702, Chicago, IL 60611

Experience luxury living at its finest in this exquisite east-facing 3200 SqFt residence at the prestigious Park Tower, part of the 5-star Park Hyatt. Located at 800 N. Michigan Ave., this stunning u...
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63 E Elm St, Chicago, IL 60611

Ultra charming, classic Chicago Greystone home on one of the Gold Coast's best blocks, just steps from the lakefront and some of the best shopping and dining. Restored to perfection, this home offers...
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180 E Pearson St Unit 3805, Chicago, IL 60611

IMPROVED PRICE OFFERS ELEVATED LIVING, NOW WITHIN REACH... This exceptional residence was built with timeless features and all of the latest modern home automation. It is located in one of Chicago's ...
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225 N Columbus Dr Unit 7107, Chicago, IL 60601

Gorgeous lake vistas grace this opulent 1-bedroom, 1-bathroom condominium at AQUA. Snaidero cabinets adorned with both over and under cabinet lighting, Kitchen Aid stainless steel appliances, a glass...
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159 E Walton Pl Unit 6B, Chicago, IL 60611

Discover the exclusive opportunity to reside in the prestigious Palmolive Building with this elegant 1-bedroom, 1.5-bathroom condo at 159 E Walton Place, Unit 6B. This meticulously maintained offers ...
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175 E Delaware Pl Unit 9102, Chicago, IL 60611

Exquisite Penthouse in the Northwest corner of the 91st floor in the prestigious Hancock building. Breathtaking North views of Lake Michigan all the way to the North Shore. Romantic sunsets stretch...
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2020 W Webster Ave Unit 1W, Chicago, IL 60647

Halcyon Development now delivering massive extra-wide, extra-large units on up-zoned lot. This stunning building blends classic Parisian elegance with modern functionality, offering a sophisticated l...
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175 E Delaware Pl Unit 5402, Chicago, IL 60611

Breathtaking views, memorable sunrises, and iconic sunsets are only the beginning for this one-of-a-kind, exquisitely renovated home on the 54th Floor of Chicago's iconic "Hancock Building." No matte...

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