By:Judy Koutsky

This Midwestern gem is a quick flight from New York and is the perfect setting for a romantic long weekend, or a family trip done in style.

Where to Stay:

Centrally located to Michigan Avenue, The Palmer House, A Hilton Hotel ( is not only the epitome of romance, but a classic, grand dame of Chicago's history dating back to 1871. For a city known for its architecture, the hotel combines old-world grandeur with modern luxury and amenities with over 1,640 rooms.  Lockwood Restaurant & Bar serves up fresh, globally-influenced, farm-to-table contemporary American food with ingredients from the hotel's rooftop garden, apiary and subterranean mushroom garden. For romance, request the Hip & Historic Suite, a spacious 1 bedroom that includes a parlor, dining room and wet bar area and take the History is Hott tour, led by Resident Historian Ken Price; which revolves around a love story.

For family friendly travel stay at the Four Seasons Hotel Chicago ( which overlooks Lake Michigan and the famed Chicago Skyline. Tents can be set up in any suite and include a cozy feather bed, blanket and pillow along with a plethora of kid friendly treats and amenities including a kids' clubroom as well as a pizza making class.

Where to Eat:

For amazing Chicago pizza head to Bar Toma ( This Gold Coast restaurant has some great gourmet, wood-fired pizzas created by James Beard Award Winner and Top Chef Master Tony Mantuano. Try the burrata pizza, which has truffle oil, Brussels sprouts and fresh burrata. Delectable non-pizza items include braised short ribs and a huge selection of craft beers and creative cocktails.

Good beef is the other Chicago mainstay and nobody does it better than Weber Grill ( From their award-winning burgers, slow-smoked regional BBQ and hand-cut Black Angus steaks all meats are served fresh from the famous Weber charcoal kettle grill. The open-kitchen lets you watch the chef prepare your meal on these giant open flame grills. The large tables and friendly service serves up Midwestern hospitality along with the amazing food.

Where to Get Pampered:

The Exhale Chicago spa ( is a great place for a massage, facial or a barre class. A full schedule of Core Fusion barre, cardio, yoga, and high intensity interval training classes are offered daily in the contemporary studio space, while the spa features a diverse menu of treatments (I recommend the signature massage, Flow). The eucalyptus steam room and Zen lounge are not to be missed.

If you're traveling with your hubby, the Waldorf Astoria Spa ( is the place for couple time. The men's locker room is souped up with a fireplace, lounge chairs plus TV (yes, only in a men's locker room would a TV be a big draw). The wet features include a sauna, steam room and Jacuzzi. Women will love the 14,000 square foot spa that includes a relaxing combinations of granite, natural stone and soft white accents. They have an extensive menu of treatments including the Ashiatsu deep tissue massage, the Silk Peel facial and the Waldorf Cleanse, a combination of a scrub, wrap and full-body massage.

What to Do:

A quintessential luxe experience is Afternoon Tea at The Drake Hotel ( which has served everyone from Princess Diana, Queen Elizabeth, to the Empress of Japan. Held in the Palm Court, the event features live, harp music, 17 different types of tea, an array of crust-less finger sandwiches, Petit Fours, and plenty of sweets including English Scones served with preserves, lemon curd, and English Devon cream.

Explore the numerous cultural and artistic attractions of Chicago with the the Chicago CityPASS ( which is a great way to skip the lines and get special treatment.  From  the world-renowned collections at the Art Institute, to getting 360 views of four states from the glass-floor ledge on the 103rd floor of the Willis Tower as well as the Shed Aquarium and the Adler Planetarium there is never a shortage of wonderment to explore.

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