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How I Rocketrip: Anthony Perez of Tapad Goes to Chicago

Honolulu, Omaha, Boston and 65 other American cities have a higher average wind speed than Chicago. That fact lends credence to the theory that Chicago's "Windy City" moniker derives less from its weather than from its residents' propensity for blustering civic promotion.

Meteorological records aside, Chicagoans do have a lot to boast about: fantastic architecture, delicious food, beautiful parks, and so much more. Anthony Perez, Account Manager at Tapad, recently traveled to Chicago from his home in Dallas. We caught up with him after his trip to see what he had to say about a city that's second to none.

What brought you to Chicago?
We had our regional team outing along with some internal meetings and training sessions.

As an account manager, do you see any parallels between your colleagues in sales competing to close deals and competing to save on trips?
With the introduction of Rocketrip I now find it fun to see if I can beat the budget. The motivation comes from the awesome rewards Rocketrip offers for saving Tapad money.

Nice job beating both your flight and hotel budgets. Any tips for finding travel deals?
If you’re not too picky on your hotel brand, or you like an element of surprise, I suggest using Priceline Express Deals. I seem to find great hotels without the high price.

You redeemed some of the Rocketrip points you earned on this trip for Elevate points to use with Virgin America. Do you have a destination in mind?
Virgin America has great direct flights to SF and NYC out of Dallas. I’m thinking one of those destinations for a quick weekend getaway.

Let's pretend your meeting was cancelled. Get in touch with your inner Ferris Bueller and tell us what you'd do with a day off in Chicago.
Being as I am from the Midwest, I have a ton of friends in Chicago. I’d definitely take the free time to meet up with some of my college buddies.

The second tallest president, Lyndon Johnson, hailed from Texas, the state where your trip started. The tallest president was of course Abraham Lincoln, of Illinois. For fifty bonus Rocketrip points, who was the third tallest?
Gonna give this my best Jeopardy impressions and say “Who is Thomas Jefferson?”

Since it's impossible for us to prevent you from looking online to see that the answer to that question is Thomas Jefferson, we'll just give you the points and ask about your hotel instead. How'd you pick where to stay, and how was it?
I clearly didn’t read ahead haha … Since I used Priceline Express Deals I picked a section of Chicago and the rest was left to chance. Although the hotel was a bit of a hike to the office, the accommodations were great, and I can’t complain.

What's your favorite Chicago specialty? Deep dish pizza, Chicago-style hot dogs, Garrett's popcorn, something else?
Definitely the pizza! I actually order Chicago-style pizza online and have it shipped to Dallas.

In honor of the Second City, which of these Chicagoans is the Greatest Second Banana?

  • A) Scottie Pippen (Michael Jordan)
  • B) Stedman Graham (Oprah Winfrey)
  • C) Jim Belushi (John Belushi)
  • D) Roger Ebert (second, in name only, to George Siskel)
  • E) Kanye West (Jay-Z. Or Kim Kardashian. Or, if you ask Kanye, no one)

Kanye West. Without Kim K. he would be pretty irrelevant nowadays.

Thanks to Anthony for telling us about his trip! Read on below for more Chicago travel tips from the Rocketrip team.

Chicago L

Getting Around Chicago

  • Airports: Chicago’s primary airport is O’Hare International (ORD) on the Far Northwest Side. Midway International (MDW), the city’s secondary airport, is located closer to the Loop on Chicago’s Southwest Side, and is dominated, appropriately enough, by Southwest Airlines.
  • The L: What the subway is to New York, the Metro to Paris, or the Tube to London, the L is to Chicago. Putting aside the question of whether it might not have been better to use underground stations in a city known for brutal winter weather, Chicago’s distinctive elevated trains go all over the city, including to both airports. Fares are cheap too at only $2.25 a ride.

What to Eat in Chicago

It’s no exaggeration to say that Chicago as we know it exists because of food. In the nineteenth century, the city rose to prominence as the site of the nation’s largest stockyard and slaughterhouse, and before that, it was a Native American trading settlement named after the shikaakwa, or wild onions, that grew on the marshy banks of the lake.

While Chicago has a world-class fine-dining scene, it's better known for hearty and humble fare. Bring your appetite, forget about calories, and visit one of these spots known to sample some local specialties:

  • Deep Dish Pizza: New Yorkers contend that Chicago-style deep dish, by virtue of its thick crust and pools of melted cheese buried under a layer of sauce, should technically be classified as a deviant variety of casserole. Chicagoans counter that even the most cursory etymological analysis suggests that the term “pizza pie” aligns most closely with their interpretation of the dish. Indeed, the pizzas at Pequod’s are distinctly pie-like. Crispy in some places, gooey in others, simultaneously savory and sweet, and requiring a fork and knife to consume, we can all agree that these extravagant concoctions - whatever you call them - won’t leave you room for dessert.
  • Chicago-style Hot Dog: Chicagoans also take a maximalist approach to this New York favorite. The Chicago Dog is an all-beef frankfurter on a poppy seed bun, topped with yellow mustard, chopped onions, sweet relish, spicy pickled peppers, tomato, dill pickle spears, and a dash of celery salt. Jimmy’s Red Hots serves one of the best around.
  • Italian Beef Sandwich: Sandwich enthusiasts will want to make the trip to Johnnie’s Beef in suburban Elmwood Park to sample their classic rendition of a Chicago favorite: thin-cut, slow-roasted sirloin served dripping in juices on an Italian roll and topped with sauteed peppers.
  • Popcorn:Somewhere in the pantheon of culinary combinations, next to peanut butter and jelly and chicken and waffles, there’s a spot reserved for Garret’s caramel and cheese popcorn.

Where to Stay in Chicago

Readers of Erik Larson’s The Devil in The White City might be wary when searching for a place to stay in Chicago. That best-selling book (a worthy addition to your business trip reading list) tells the story of H.H. Holmes, who in addition to running a popular budget hotel during the 1893 World’s Columbian Exposition, was also one of the most prolific serial killers in American history.

Holmes’ World’s Fair Hotel, colloquially known as the Murder Castle, has since been razed. A post office now occupies the land where it once stood. Here are some other/better hotel options to consider:

  • Virgin Hotel Chicago: Having already tried his hand in industries ranging from music to cell phones, airlines to space tourism, Richard Branson has decided to open a chain of hotels, and the first U.S. location is in Chicago.
  • Hotel Cass: A uniquely-branded boutique outpost of the Holiday Inn Express, located in the heart of Chicago’s Loop.
  • Freehand: The Freehand hostel caters to the type of young traveler who’s looking for stylish design and affordable luxury, not just a place to drop off a backpack. If you’re not up for bunk beds, private rooms are also available.
  • Or, live like a local at one of the Best Airbnbs in Chicago.

Want to earn rewards for spending less on your next business trip? Request a demo from Rocketrip to see how much you could earn by saving your company on flights, hotel, and rental cars.

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