Chicago Vacation Rentals Near the Mag Mile

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In the Windy City, there’s an amenity as coveted by young professionals as bottle service at Underground: a rooftop pool.

Pools in downtown Chicago are about as rare as seven straight days of 90-degree weather and as universally loved. If someone has the hookup, you jump on it.

In vacationland, hotels aren’t much help in that department. Very few have pools that are outdoors, which is a head scratcher considering just how many visitors descend upon the Windy City during this popular festival and convention season.

That’s where the customers of Chicago vacation rentals have the last laugh. Many of the high-rises in Streeterville, the Gold Coast, River North and the Loop have mezzanine-level or rooftop pools, the ideal cool-off point after a long day of shopping on the Magnificent Mile or strolling around Millennium Park.

Yep, you heard it right: The Windy City actually gets a summer, and a nice one at that.

At post time, the temperature is 77 degrees, slight breeze, with a high of 93 expected later.

Besides pools, condos like the two-bedroom one pictured come with extra conveniences for all ages, whether you’re planning a girlfriends’ getaway or a family excursion to Navy Pier. In the Shore Club, guests are spoiled with floor-to-ceiling windows, a full-size kitchen, fitness room, hot tubs and a substantial park, where on a good day, you can hear the concerts from the nearby Petrillo Band Shell.

Get ready for those friends at home to have major vacation envy.

Posted in Lake vacation homes, Mancations, Midwest vacations

About Valerie

Valerie Moloney is your resident blogger and the Expansion Markets Editor for, who oddly enough, feels panicked when asked, "What's the best place to eat in Chicago?" or her favorite, "It's my birthday. Where should we go with a party of six?" No stranger to travel--and traveling with kids--she is a young mom who ODs on the Internet when it comes to planning family trips or buying clothes. Here's hoping she finds you the vacation you deserve.

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