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Chicago is a city of 77 neighborhoods, 2.7 million people, and spans 234 square miles!

See some of the beautiful sites that Jocelyn + Katie were able to visit on their recent trip to the Windy City and sign up for your trip today: http://bit.ly/2yK9BVa



Testimonial Tuesday: Heath + Margaret

Q: Why did you sign up for your trip? What were you looking to get out of it?

A: Heath and his colleagues were talking about your website at lunch one day. He came home and told me about it. We decided that now that we were empty nesters, it might be fun. We love to travel and liked the idea that someone else were going to make the plans. We were looking for a new adventure!!

Q: Did you have any hesitations about taking a surprise trip? Were you nervous?

A: No, we really had no hesitations. Our only concern was that because we picked a budget on the lower end, we wouldn’t have the experience we were hoping for. We really did not want to take a train or bus. We were sure we would have a good time because we love to travel together. This time the anticipation of the trip was a lot of fun. We had many conversations about where we were going and what we were going to do. We also did a small contest on Facebook. We posted the information that we had (except the weather report). We told our friends that the first person to get the destination right would win a prize from that city. This got all of our friends talking and as excited about our trip as we were.

Q: Where did you guess you were going to travel? Were you surprised by the destination?

A: From the beginning, we guessed Chicago because we noticed that you send a lot of people there. We were also thinking New England somewhere. Once we got the weather report, we were pretty sure that we were right with Chicago. So, no, we weren’t that surprised when we opened the envelope.


Q: Upon discovery of your destination, what were some of your perceptions about the city prior to your trip?

A: We knew Chicago was very large, so we assumed it would be a lot like NYC. We had never even considered a trip to Chicago, so we had no preconceived notions of what to expect. We knew we wanted to see a baseball game, so having a city with 2 baseball teams was good news for us.We departed from the closest airport which was helpful. The hotel was geared towards adults and couples. In the survey we specified good food and cultural attractions as activities that we enjoyed. Chicago certainly had both of those options.

Q: What made the trip feel unique and tailored to you?

A: We departed from the closest airport which was helpful. The hotel was geared towards adults and couples. In the survey we specified good food and cultural attractions as activities that we enjoyed. Chicago certainly had both of those options.


Q: What did you like most about your travel accommodations?

A: The direct flight was easy. The Palomar Hotel was perfect for us. It was in a beautiful part of the city where we felt perfectly comfortable walking. It was across the street from a subway station and at a major intersection for buses.


Q: What was your favorite experience that we recommended for you?

A: The Art Institute of Chicago was on the itinerary, so we made this our first stop.

Q: What did you discover on your own (not on your itinerary) in your destination that you feel is share-worthy?

A: We were able to get tickets to the Cubs baseball game on our second day in Chicago. We really enjoyed immersing ourselves into the local culture. Sports fans tend to be very friendly people, so we had a good time cheering on the World Series Champions.


Q: What was your favorite part of your trip?

A: Being together on a new adventure. We discovered a new city that we have never even considered before. This experience is something we will talk about for years to come.

Q: If you could do the trip over again, what would you do differently?

A: We really can’t think of anything that we would do differently.

Q: What did you learn on your trip, or from your trip?

A: Chicago is a much nicer place than we thought it was going to be. If we ever plan our own vacation to a major city, we will make sure that our hotel is near a subway station.


Q: How would you describe Pack Up + Go and your experience to your friends and family?

A: We have already told them that is was fantastic. It is a unique and fun travel experience. We would tell them to let go of the planning and just “go with the flow”. (If you knew us, this is a very big deal. We plan everything.)

Q: What would you say to someone who is hesitant to go on a surprise getaway?

A: "How bad could it be as long as you are with someone you care about and have fun with?“


Wanna chow down in Chi-town or another great American city? Check out the travel survey today: http://bit.ly/2f8E6Zp