Vacation Rentals in Chicago, Illinois

Rene Syler is headed to Chicago, Illinois, where best friends Mindy and Erica are looking for a vacation rental property that not only suits their personalities but also their wallets. With a budget of $250 to $350 per night for a long-weekend getaway, the ladies hope to find a space that fits the bill.
Chicago is a world class city with a touch of everything -- amazing architecture, delicious dining, a tremendous music scene and luxury shopping! Not to mention its top of the line sports culture.

'Chi-Town' is America's third largest city, and is located in northeastern Illinois, on the southwestern shores of Lake Michigan. The city's architecture is some of the finest in the world! In fact, Chicago is the birthplace of the modern skyscraper. Visitors merely need to look around The Loop, otherwise known as downtown Chicago, to see the city's incredibly skyline.

Amongst the top tourist attractions in town are the Navy Pier and Millennium Park. And don't forget its 26 miles of 33 beaches along the Lake Michigan shoreline!

But as the locals say, Chicago really is the city of neighborhoods -- whether it's the hip and trendy Wicker Park, the historic Old Town, or the lovely and classic Lincoln Park, there's something for everyone. And, for best friends Mindy and Erica, the Windy City is just what they're looking for.

"Typically we like to go somewhere that has a beach and sun and lots to do," Mindy explained. "But we wanted try something different and go to a bigger city to see how that is for a vacation."

The perfect Sweet Retreat would have the following criteria:

  • Two bedrooms
  • Located in a cool neighborhood
  • Accessible to shopping, dining & attractions
  • Outdoor space
With a budget of $250 to $350 per night, Rene wants to show the ladies three different areas -- the Bucktown neighborhood, Graceland West, and the Lakeview neighborhood.

The Bucktown House: The Bucktown House is a comfy, cozy space that sits at 850 square feet. Although it has two bedrooms, there's just one bathroom, posing a bit of a challenge for the ladies! But what the rental lacks in size, it makes up for in decor and outdoor space. With a beautiful patio that encompasses Chicago charm, the $311 a night price tag seems right on point. But will the tight quarters deter Mindy and Erica from enjoying this lot? For more information on this property visit

Graceland Carriage House: Just seven miles away from downtown Chicago sits the Graceland Carriage House. At 1,200 square feet, with two bedrooms and one-and-a-half bathrooms, this quirky property has a personality of its own. Although it's been revitalized, the initial property dates back to 1898! With pops of color everywhere, and a beautiful large outdoor patio, the ladies are in love! And with a price of $333 a night, it's within their budget. But will the distance from town drive the pair away from the property? For more information on this property visit

Southport Suite: Just around the corner from Wrigley Field is the conveniently placed Southport Suite. With readily accessible public transportation, and the town of Lakeview within arm's reach, the ladies love the location! And there's no shortage of space within the rental -- it is 1,200 square feet with two bedrooms and one bathroom. Mindy and Erica feel confident in the confines but with a price tag of $379 per night, will the cost bust their budget? For more information on this property visit

For more information on Chicago visit

Segment 1
Bucktown House for Rent in Chicago, Illinois
Bucktown House for Rent in Chicago, Illinois
Best friends Mindy and Erica are scouring Chicago for the perfect long-weekend retreat. Rene Syler will show the ladies properties in three unique areas. The first property is Chicago's hip and trendy Bucktown neighborhood.
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Segment 2
Graceland Carriage House for Rent in Chicago, Illinois
Graceland Carriage House for Rent in Chicago, Illinois
Mindy and Erica are looking for a place to call home for their three-night stay in Chicago. After touring a cute coach house in the Bucktown neighborhood, the friends are headed to Graceland West!
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Segment 3
Southport Suite for Rent in Chicago, Illinois
Southport Suite for Rent in Chicago, Illinois
Best friends Mindy and Erica are hunting for the perfect retreat for a long-weekend getaway in Chicago. So far, they have toured two vacation rental properties. The last property is in the city's fun Lakeview area.
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Photo Gallery
Photos: Rental Properties in Chicago, Illinois
Check out three vacation rental properties in Chicago, Illinois.
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