Search Vacation Homes in Chicago 59th Street Station

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Our top choices for Chicago 59th Street Station vacation homes

Lux Home in Chicago 7mins Downtown

Lux Home in Chicago 7mins Downtown
Bronzeville
9.8 out of 10, Exceptional, (28)
"Larry was super responsive, the property was spotless, the location perfect. Our group of friends loved it. We will be back! "
United States
Kyle B.
Lux Home in Chicago 7mins Downtown

Cheerful 4 bedroom smart home w/ indoor fireplace

Cheerful 4 bedroom smart home w/ indoor fireplace
Washington Park
8.0 out of 10, Very Good, (19)
"Conveniently located just south of downtown. The space was cavernous! Plenty of room and stylishly decorated. Good communication from the host throughout our stay. "
United States
Anonymous traveler
Cheerful 4 bedroom smart home w/ indoor fireplace

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Hyde Park
10.0 out of 10, Exceptional, (15)
"The check-in process was effortless and the kitchen was well appointed."
United States
Theophlius K.
Gorgeous historic mansion on UChicago campus. Renovation with original detail.

Woodlawn Oasis...10 Minutes to Dining & Downtown

Woodlawn Oasis...10 Minutes to Dining & Downtown
Woodlawn
9.2 out of 10, Wonderful, (14)
"I would book the house again"
United States
Marilyn W.
Woodlawn Oasis...10 Minutes to Dining & Downtown

LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins
Bronzeville
9.4 out of 10, Exceptional, (11)
"Property matched the pictures perfectly! Loved the updates and appreciated the abundance of towels, dishes, etc! 3rd floor walkup if thats an issue for you. Also felt safe and secure. Great neighborhood too! Host provided detailed, easy to understand instructions for the property and was accessible via the VRBO app! "
United States
Marquita S.
LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

Ahh-mazing Home, rooftop deck, near lake front. Easy commute to Navy Pier/Loop.

Ahh-mazing Home, rooftop deck, near lake front. Easy commute to Navy Pier/Loop.
Kenwood
6.0 out of 10, (2)
"Great property"
United States
Anonymous traveler
Ahh-mazing Home, rooftop deck, near lake front. Easy commute to Navy Pier/Loop.

Scott House of Woodlawn - Incredible 3-bedroom house in Chicago; AC and extras

Scott House of Woodlawn - Incredible 3-bedroom house in Chicago; AC and extras
Woodlawn
Scott House of Woodlawn - Incredible 3-bedroom house in Chicago; AC and extras

4-bedroom townhome in superb Chicago

4-bedroom townhome in superb Chicago
Kenwood
4-bedroom townhome in superb Chicago

Charming Bronzeville Oasis

Charming Bronzeville Oasis
Bronzeville
Charming Bronzeville Oasis

Remote Worker Special: 2-bedroom townhome in Jackson Park Highlands neighborhood

Remote Worker Special: 2-bedroom townhome in Jackson Park Highlands neighborhood
South Shore
Remote Worker Special: 2-bedroom townhome in Jackson Park Highlands neighborhood
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chicago 59th Street Station Hotel Reviews