In-Town Getaways

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From the archives: July 09, 2009

Save those frequent flyer miles, and plan a staycation instead. Chicago is filled with hotels, restaurants and activities that will lift you out of the Midwest to the exotic locales of your vacation dreams. Discover where to get away from it all, without flashing your embarrassing passport photo. Home voyage!

(Photo courtesy of the InterContinental Chicago)

On this page:Where to Play, Where to Nosh, Where to Stay.

Where to Play

  1. 1 4 Star Rating: Recommended Untouchable Gangster Tours
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    10924 S Prospect Ave (Tour starts at 600 N Clark), Chicago, IL 60643 (map)

    Time travel counts, too! Climb aboard the big, black bus and go back to Prohibition-era Chicago to relive the days of mob bosses, bootleggers and bagmen. You'll be guided through neighborhoods all over the city to see first-hand where the near-mythical tales of Chicago's checkered past went down.

  2. 2 Windy City Sailing, Inc.
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    3623 N Leavitt, Chicago, IL 60618 (map)

    When was the last time you made use of that huge blue expanse just east of Lake Shore Drive? Dust off your Top-Siders and imagine you're catching breezes off the Amalfi Coast as you sail Lake Michigan in a custom yacht. Whether you want to learn the ropes yourself or just sit back and let the waves lull you to sleep, you'll be in good hands with United States Coast Guard-certified captains manning the decks.

  3. 3 4 Star Rating: Recommended mySpa at the Fairmont Chicago
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    200 N Columbus Dr, Chicago, IL 60601 (map)

    Derived from ancient Japanese cleansing and purification rituals, the multi-step Vitality body treatment offered at this Loop hotel's tucked-away spa is like a far-Eastern retreat for your senses. The voyage begins with a gentle yuzu body wash and stimulating bamboo gingergrass scrub, progressing to a softening rice body polish and a massage with Japanese kinmokei flower oils. Just close your eyes--it's a breeze to picture yourself far, far away.

Where to Nosh

  1. 4 4 Star Rating: Recommended A Mano
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    335 N Dearborn St, Chicago, IL 60610 (map)

    Take a vacation in Italy, right in River North, with this sub-street level trattoria's Roman-style wood oven-fired pizzas, handmade pastas and all-Italian wine list. Did we mention the revolving assortment of house-made gelato and sorbetto? It's so authentic, you might catch yourself looking for the Trevi Fountain on Daley Plaza.

  2. 5 5 Star Rating: Highly Recommended Fonda del Mar
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    3749 W Fullerton Ave, Chicago, IL 60647 (map)

    Seafood-centric Mexican food like olive- and Serrano pepper-laced marlin seviche, plus margaritas made with top-shelf tequila and sun-drenched yellow walls make it easy to pretend you're supping on a beach in Playa del Carmen instead of in a tiny storefront on an aesthetically challenged stretch of Fullerton Avenue.

  3. 6 4.5 Star Rating: Recommended Trader Vics - Chicago
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    1030 N State St, Chicago, IL 60610 (map)

    Every night is an island tiki party at this kitschy, 1930s throwback restaurant in the Newberry Plaza building. If the bamboo-heavy, thatched room with the requisite tiki dolls doesn't put you in a vacation state of mind, we have a feeling the Scorpion Bowl, a communal rum cocktail for four, will do the trick.

Where to Stay

  1. 7 4.5 Star Rating: Recommended Drake Hotel
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    140 E Walton Pl, Chicago, IL 60611 (map)

    Decades of Chicagoans searching for a taste of pinky-out London-town propriety have found it in spades at this Mag Mile hotel's legendary high tea, served in the opulent, ruby- and gold-swathed Palm Court. Suites offer sweeping views of Lake Michigan.

  2. 8 3.5 Star Rating: Average InterContinental Chicago
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    505 N Michigan Ave, Chicago, IL 60611 (map)

    This luxurious downtown hotel has a secret draw: the junior Olympic-sized swimming pool nestled on the twelfth floor, decked out with ornately painted tiles, white columns and potted palms. A few laps, and you’ll feel closer to the sultry Mediterranean Sea than the hectic street scene below.

  3. 9 5 Star Rating: Highly Recommended Sofitel Chicago Water Tower
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    20 East Chestnut St, Chicago, IL 60611 (map)

    This stunning, contemporary hotel near the bustling Rush Street dining and nightlife scene exudes modern luxury with a French accent. From the "bonjour" welcoming you at the reception desk to chef Martial Noguier's seasonal French cuisine at the hotel's restaurant, Cafe des Architectes, you'll swear you're in the city of light.