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Vacation Homes for Sale in Chicago, IL

53 homes
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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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4676 W Peterson Ave, Chicago, IL 60646

Welcome to Your Dream Home in Sauganash! This spacious, new construction home is designed with an entertaining life in mind. With a total of 7 bedrooms and built on a double lot (45 x 120), there's...
Price drop
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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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77 E Cedar St, Chicago, IL 60611

Luxury Brownstone Masterpiece on Cedar Street - Offered at $4.5M Step into unparalleled elegance and modern luxury with this newly constructed brownstone on Cedar Street, situated in one of Chicag...
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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 ...
Price drop
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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...
New
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4047 W Crystal St, Chicago, IL 60651

SPECIAL HOMEBUYER FINANCING AVAILABLE ON THIS HOME! Details below. DON'T MISS this fantastic 4 bedroom, 3 full bath sprawling brick home on tree lined Crystal street. Built in 1999, this stately bric...
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940 W Glenlake Ave Unit 30B, Chicago, IL 60660

Experience unparalleled lakeside living in this exquisitely redesigned 2 bedroom + office, 2 bathroom Edgewater condo, boasting iconic and unobstructed views of the lake, beaches, parks, and city in ...
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555 W Cornelia Ave Unit 1201, Chicago, IL 60657

Please take the time to visit this Sunny and Spacious 2 Bdr-2 Baths corner unit in East Lake View! Open concept kitchen that offers plenty of cabinets and all 4 appliances, dining room area shared wi...
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6157 N Sheridan Rd Unit 19A, Chicago, IL 60660

Be the first one to live in this brand new, gut rehabbed, 3bed, corner condo, which also has a balcony. Finishes inside are to the highest standards. Contemporary, soft-close kitchen cabinets with u...
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1414 N Wells St Unit 201, Chicago, IL 60610

Looking for the perfect place in the heart of Old Town? Check out this chic, sun-drenched and sophisticated 2 bed/1.5 bath renovated condo. Located in a sought-after boutique elevator building, this ...
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1000 N Lake Shore Dr Unit 1406, Chicago, IL 60611

Prime Gold Coast Location Just Steps from the City and Lakefront! Enjoy stunning lake views from both the living room and bedroom, overlooking Chicago's renowned Oak Street Beach. This updated 1-bed,...
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100 E Walton St Unit 33A, Chicago, IL 60611

Live in the best managed Gold Coast highrise. Pristine sunny one bed/one bath designer unit lovingly upgraded to perfection. OPE...
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201 E Chestnut St Unit 7E, Chicago, IL 60611

Pristine and freshly painted over-sized 1 bedroom, 1 bath condo in a prime Streeterville boutique building. Enjoy fresh air from the private, recently renovated, north facing balcony with access fr...
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950 N Michigan Ave Unit 2203, Chicago, IL 60611

Amazing opportunity! Bring your architect and designer to help you create a one-of-a-kind showplace. With glorious views overlooking the city, beach, and Lake Michigan - and the BEST PRIVATE TERRACE ...
Price drop
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1460 N Sandburg Ter Unit 2304A, Chicago, IL 60610

"Property is currently rented through September 30th, 2025" This north facing convertible studio has sweeping views of the lake, park and one of the association 2 swimming pools. The newly painted u...
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3440 N Lake Shore Dr Unit 14B, Chicago, IL 60657

Welcome home to this BRAND NEW rehabbed 2 bedroom 1 bathroom condo with unparalleled vistas of Lake Michigan and Belmont Harbor. Located in a prime spot on Lake Shore Drive, this unit features a spac...

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