Business Travelers

How I Rocketrip: Caitlin Sweeney of Yieldbot Travels Cross Country

Here at Rocketrip HQ, not a week goes by without an instance of travel saving that blows our minds, drops our jaws, and otherwise amazes us to the the point of physical discomfort. It’s one of the occupational hazards of lowering average trip costs by nearly 30%.

Caitlin Sweeney is one business traveler whose ability to save hurts us so good (Warning - The feathered hairstyle sported by John Mellencamp in this video is so extravagently eighties that it almost qualifies as NSFW). Caitlin's a Senior Account Manager at Yieldbot, though her business card should also read Travel Savings Boss. She recently completed a two-week trip that took her from her home in New York City to Texas, Illinois, Wisconsin, and California - and that earned her over $1,500 in Rocketrip rewards. We caught up with Caitlin to talk about how she saved, what she packed, and whether there’s such a thing as too much queso.

You stayed with friends in Austin, Chicago and Santa Monica. Any advice for how to be a good guest? Do you bring gifts, take your host out to dinner, or return the favor by opening up your home?
When I'm traveling for work and staying with friends, I try and give them as much of a heads up on my schedule as possible. Typically I have time to either take them to dinner or drinks, but sometimes I'm pretty busy and just bring them a bottle of wine when I arrive!

Is this the longest work trip you've been on?
Yes! Two weeks on the road! Thirteen days and six cities. Although it was long, it was really productive and didn't feel too exhausting.

How'd you decide what to pack? 100 bonus Rocketrip Points if you managed to get by without checking a bag.
I had to pack for the heat of Texas, a music festival in Eau Claire, Wisconsin with clients, meetings in Chicago, and a networking event in L.A. That being said, I was very thankful it wasn't winter and I could pack all dresses! I always use a soft carry-on bag, but this time I went with a small duffel (for the festival weekend) inside a rolling carry-on suitcase. Going into the first week of the trip, I had to check my bag because I had bug spray/sunscreen/campaign provisions but after the festival I tossed those liquid items and went carry-on the rest of the trip!

Is there any food you especially enjoyed on this trip?
In Texas I ate ALL of the Tex-Mex. I think I had queso 5 days in a row. In Chicago I go for the Chicago-dogs (since I get pretty solid pizza in NYC)!

Did you get to do anything fun on this work trip?
After traveling to these cities over the past year, I've met a lot of clients and friends that I love to spend time with when I'm on the road, so I always try to make time to do some fun things. That being said, everything we do with our clients tends to be on the fun side!

In your opinion, what's more daunting: Texas in the summer or Chicago in the winter?
I'm originally from Minneapolis, so the cold doesn't scare me as much as the 102 degree heat in Texas!

You're going to earn $1,683 in rewards on this trip. Congrats! Any idea how you'll spend it?
Traveling! :) I'm heading to Barcelona at the end of the month for my birthday, so I'm excited to use my work travel perks for personal use!


One of the best parts about going on a work trip to Dallas, Chicago, and Santa Monica is you're never far from a high-quality Ferris wheel.

Did You Know?

  • If Caitlin wanted to add a few more days to her already lengthy trip, she could have driven all 2,278 miles of historic Route 66. America’s most famous highway starts at Chicago’s Lake Shore Drive and terminates at Santa Monica’s Pacific Coast Highway.
  • Whether intentionally or not, Caitlin managed to fly through four of the five busiest airports in the country on this trip: New York-JFK, Dallas-DFW, Chicago-O’Hare, and Los Angeles International. For those of you keeping score at home, Atlanta’s Hart Jackson Field, the only airport she missed, is the busiest in the United States.

What to Eat?

  • Austin - In its most recognizable form, a Tex-Mex restaurant is one that serves Mexican comfort food in Texas-sized portions, accompanied by vast quantities of chips and queso. Curra’s Grill in South Austin follows this script while adding a few twists, like an avocado margarita that’ll make you wonder why you ever wasted time drinking anything else.
  • Dallas - The pizza and pasta served at Campisi’s Egyptian Restaurant is decent; indeed, surprisingly so given the restaurant’s name and the fact that Dallas is hardly known for its Italian cuisine. But the local chain’s appeal is based more on infamy than on food. The original location on Mockingbird Lane was reputed to be a mob hangout, and Jack Ruby was a regular. Joseph Campisi even visited him in prison the week after Ruby shot Lee Harvey Oswald.
  • Chicago - A Chicago-style hotdog is an all-beef frankfurter topped with chopped onions, sweet green relish, tomato, a dill pickle, spicy peppers, celery salt, and mustard, but never - ever - ketchup. Chicagoans disagree over where to get the best dog in the city. Portillo’s has built a mini-empire serving their version, along with Chicago specialties like the Italian beef sandwich. Gene and Jude’s is a smaller scale operation, with a single location near O’Hare Airport, but their hot dogs can compete with anyone else's.
  • Santa Monica - Southern California is a laid back place, but it’s also three hours behind the Eastern Time Zone, meaning that for many people the workday has to start early. That might explain why there are so many donut shops in the otherwise health-conscious city of Los Angeles. One of the best is Primo Donuts in West L.A. just over the border with Santa Monica.

Rocketrip recommends a balanced diet of Tex-Mex in Austin, hotdogs in Chicago, and donuts in L.A.

Where to Stay

Friends are nice, but so are these hotel options:




Santa Monica

A stranger is just a friend you haven't yet met. In the meantime Airbnb lets you stay in their home.

What's the longest work trip you've ever been on? Share your story by tweeting to @Rocketrip.

All Tags: How I Rocketrip, Business Travelers

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