Chicago winter breakDuring a winter school break you and yours have four choices: do nothing, escape nearby, go where it’s warm, or head someplace as cold as or colder than where you are. The latter makes sense if you’re a family that skis together, but otherwise you may need a bit of motivation. So try this: A vacation package including five nights in a premium suite at the well above-average Omni Chicago Hotel, plus airfare, for around $400 per person.

The Omni’s got a swell indoor pool, all the free Wi-Fi you can drink in the lobby, and the also free Omni Kids Program that yields activity books and snacks for the kids as well as complimentary suite childproofing, should you need it. Plus, the suite itself – aside from having the parental essentials of a minibar and a 37-inch plasma flat-screen TV – realistically sleeps five, with two doubles and a sofa sleeper and no extra occupancy fees for kids 17 and younger.


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I don’t mind telling you that I found this deal by playing around with the ShermansTravel.com Travel Search price comparison tool. After selecting the “packages” tab and plugging in a few variables – that I’d be flying from NYC to Chicago with a party of five from February 20-25 – I was able to initiate a search of several sites, including Escape Wizard, which prompted me to refine my search to specify two adults and three kids. From there I was able to search several more sites, including Expedia, which in turn had me specify (again) my breakdown of adults and kids as well as their ages. The result was direct flights to O’Hare from all three NYC-area airports (Newark was only slightly higher than JFK and LaGuardia) bundled with a stay at the Omni.


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The hotel sits on North Michigan Avenue at the midpoint of the Magnificent Mile, or in the parlance of unabashed shoppers, above an Express and directly across the avenue from the Apple store. And if the shopping grows tiresome or prohibitive, the Chicago Children’s Museum is a hearty 20 minutes southeast of the hotel by foot, and the Art Institute of Chicago as well as the McCormick Tribune Ice Rink in Millennium Park (pictured, skate rentals $10) are about a 20-minute walk from the hotel, due south on Michigan Avenue.

One more thing: In case you think I’m alone in assuming travelers will be willing to roam Chicago next month, February 18-27 happens to be Chicago Restaurant Week, when more than 200 of the city’s restaurants will feature prix fixe lunches upwards of $22 and dinners starting at $33 and $44.

For general trip-planning information, see our Chicago Travel Guide.

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