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A post by Joylyn Tanner, Senior Communications Manager for Cloud Connect.

My mother was born in Chicago, and as a result, I have an overwhelming sense of pride for the city, Da Bears, deep dish pizza and Wrigley Field.  This affinity for the Windy City inspired me and my colleagues to cull together our top-picks on where to eat and what to see when you’re in town for Cloud Connect. With over 7,000 restaurants to choose from, more than 500 parks and a menagerie of bars, theaters, comedy clubs, etc., we’ve created an infographic that can help you navigate the goods with some short commentary below from yours truly.

Where to Eat:

Chicago is the birthplace of the beloved deep dish pizza, as well as fast food behemoth, McDonald’s and chewing gum giant, Wrigley’s.  With these notorious knocks under its belt, Chicago is sure to tantalize your taste buds during your stay.  It’s tough to narrow down, but our first staff pick for the best pie in the city is Lou Malnati’s, followed closely by Giordano’s and Pizano’s.

Italian bites run rampant in Chi-town, a couple of our faves are Rosebud on Rush and RPM Italiano.  And if it’s just a good dog you’re in search of, be sure to hit Hot Doug’s.  It’s cash only and don’t go at prime lunch time because the lengthy line will overwhelm.

If more of a scene is your thing, Howells & Hood is nestled at the base of the Tribune Building and features an unparalleled drink selection (largest draft beer selection in all of Chicago!), tasty menu and remarkable views to cap your evening.  Reservations strongly encouraged – you can’t go wrong with this choice!

If you can’t pull yourself away from the conference grounds, Hyatt Regency McCormick offers a couple dining options: Shor for a contemporary American meal, Forno if a plate of pasta hits the spot, or the lobby bar M/X for small bites and a cocktail.

Things to See:

Did you know that the first Ferris wheel made its debut in Chicago in 1893? Now Navy Pier is home to the 15-story Ferris wheel and a must-see when in Chicago.  During the week of Cloud Connect, Chicago’s Chocolate Festival is at Navy Pier and open to the public, while for those in search of some Halloween funk can check out The Fear Haunted House, also happening at the Pier. The insider’s tip here though is the stained glass exhibit that can’t be missed!

Lincoln Park Zoo is free and who doesn’t love free?!  With fall upon us and Halloween in the air, the Zoo has an events calendar you should check out prior to your visit to make sure you’re maximizing on fun, which may or may not include a Spooky Zoo Spectacular.

If you prefer setting sail, you can’t go wrong with the Architectural Boat Tours.  While on board, you’ll navigate along the Chicago River, be awed by 50+ buildings unique architecture, and learn the ins and outs of how the city grew from a small back-country outpost into one of the world’s most important crossroads.  While on the topic of Chicago history, may we recommend a Mob Tour, where you can escape into the city’s underworld of gangsters and criminals?  Problem is, tours only run Saturday and Sunday, so if you’re in early or sticking around after the event – secure your spot now to learn about all the old gangster hot spots.

What to Do:

If you need some greenery in your life, parks abound.  Stop by the local Bird Sanctuary off McCormick or visit Memorial, Grant or Millennium Park, which plays host to the famous “Bean.”

If a drink and a laugh is more up your alley, Second City Comedy Club will put you in stitches with their improv. Shows run nightly at 8:00 pm during the week of Cloud Connect.  Social Twenty-Five is located in the trendy River North neighborhood – just a few miles from McCormick – and has become a favorite hot spot with live music entertainment and a swanky two-level bar.  You could also belly up to the bar at Chicago classic, Pippin’s Tavern, a quintessential Irish pub located on Rush Street.

Don’t be afraid to take on public transit to get you where you want to go.  All you need to know to plan your route can be found on Chicago’s Transit’s website.

And finally, it was to my delight when Cloud Connect decided to expand to Chicago last year and return in 2013 to such a fun-loving city.  I’m looking forward to the event and being back in my mom’s hometown.   Hopefully, this can help you chart your course while in Chicago and if we missed something you’d like to share, please feel free to comment – we are all ears.

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