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  • Ross Weber
  • "One night in Chicago. What do I do?"

Ross Weber

Manhattan Beach, California

One night in Chicago. What do I do?

30-40 year olds. Guys and girls in town for a conference.

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4 Answers

  • Jay Lee

    top answer by

    There, obviously, is a never-ending answer to this question. For conference-attending 30-40 year olds, the River North/Loop neighborhoods of downtown Chicago probably will be your scene. Chicago is renowned for its dining, whether its going to one of the 19 Michelin starred restaurants, getting some Italian Beef, or, most importantly, getting a hefty slize of deep dish pizza.

    As far as night life, River North Neighborhood especially will have a good mix of bars, lounges, clubs, and everything else in between, with the crowd being a bit more upscale and older (young drunk kids tend to stick up north). Chicago also has a great jazz/blues scene, as well as an emerging brewery culture (you can go up north to visit breweries like Goose Island Brewpub and Half Acre Beer Company ).

    As for a night, take in the great skyline. I'd recommend skipping the Willis (Sears) Tower and going instead to the The Signature Lounge on top of the John Hancock Observatory . View is free, drinks are stiff (and still less than cost of admission at the Willis viewing deck).

    Another big recommendation is going to go see a show at Second City , the comedy troupe that graduated basically the who's who of sketch comedy (everyone from Belushi brothers and Bill Murray to Amy Poehler, Tina Fey and Stephen Colbert. Chicago is second to none with its sketch comedy scene, and Second City is the pinnacle of it all. They have several stages, and the Main Stage tends to have the biggest names and shows, but all of them will guarantee a great time.

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    1. Chicago (city)
    2. River North (neighborhood)
    3. Goose Island Brewpub (attraction)
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    5. The Signature Lounge (attraction)
    6. John Hancock Observatory (attraction)
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  • Brew Johnson

    answered by

    Dinner: Girl & the Goat , GT Fish & Oyster , Mercadito Chicago , or Joe's Seafood, Prime Steak & Stone Crab . Drinks at Paris Club . Late night dogs at the The Wiener's Circle. If you want to go a little more old-school for drinks, Gibsons Bar & Steakhouse or Tavern on Rush are at a restaurant and bar heavy area.

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    1. Girl & the Goat (restaurant)
    2. GT Fish & Oyster (restaurant)
    3. Mercadito Chicago (restaurant)
    4. Joe's Seafood, Prime Steak & Stone Crab (restaurant)
    5. Paris Club (restaurant)
    6. The Wiener's Circle (restaurant)
    7. Gibsons Bar & Steakhouse (restaurant)
    8. Tavern on Rush (restaurant)

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  • Lindsey Anderson

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    Definitely grab a drink at the top of the Hancock Building Worth the potential wait for the view. Also, there are bike and segway rentals that line shore. Grab one for an hour or two and venture up to North Beach and down to museum row on the boardwalk.

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  • Praveen Modi

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    Couple of drinks at top of the Willis Tower . Stunning view. Great experience!

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