Chicago Condo Rentals: Holidays in the Windy City

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Check-In, Check-Out has shown love to some wintry Colorado vacation rentals and quaint New England vacation rentals. At Christmastime, though, there’s nothing like the buzz of a big city.

If you’re tired of the old trek to the mall, hit the Windy City for it’s fabulous neighborhood boutiques and the grand dame that and fashion emporium called the Magnificent Mile. Chicago vacation rentals, thanks to a glut of condos that haven’t sold, are aplenty, especially in high-rises with amenities so nice you’ll feel like you’re living in Trump Tower.

The three-bedroom property in the photograph struts like the City of Big Shoulders with its high ceilings, granite counter tops, roomy terrace (with views of that glam skyline) and Crate & Barrel-esque furniture. This is the kind of penthouse that many Chicagoans would drool over. A Michigan Avenue condo? That’s an address akin to Park Avenue in New York (but more affordable, obviously).

Shoppers rejoice for the mile of well-known department stores like Nordstrom, Saks Fifth Avenue and Macy’s and recessionista-friendly, yet still fashion forward designs from H&M, Filene’s Basement and Zara, which opened its U.S. flagship a few weeks ago. The well-edited collections dress the girls who likes a little pizazz in her wardrobe, whether that’s a sequin blouse or cheetah coat.

And to those of you who worry about visiting Chicago this time of year: It actually hasn’t been that bad–if you count the 40s as tolerable weather.

So round up your girlfriends and get shopping. On Debit, on Visa, on MasterCard! To Chicago you go.

Posted in All-season rentals, Midwest vacations, Romantic getaways

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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