Why Chicago They Asked

Oven Grinder Pizza Pie

Ready, set, go! Time for our next trip—the Windy City! When I said this, I always got the same response: “Why Chicago?” My response: ‘If you can’t go to Italy for good pizza, you might as well go to the next best place.’ Chicago does have great pizza, but really we just wanted a place with great museums, architecture, interesting history, and delicious food. We were also looking for a place that neither one of us had explored in great detail.

I wanted to go in the fall because it’s my favorite time of year. I love all the great colors, the weather is not as hot in most places, it is not as crowded as the summer months, and you can sometimes find great deals on popular tourist destinations. Hot weather and I are not on speaking terms, so traveling when the weather is cooler makes me happy (and keeps me from spontaneously combusting). Check out Weather.com for current and projected information on what the weather will be like when traveling, which can also help narrow down the destination to your next vacation. Chicago was projected to be mild and dry during the week we chose to travel—perfect for me.

See, it’s coming together. I have the why, the when, and the who. Let’s move on to the how—which, in this case, is the budget. My husband always gives me a challenge on how much to spend and often I get close to meeting his challenge. We’re quite competitive. I look at how much we have to spend and I break down where that money is going to go. Then I add about 20 percent for the “Oh crap, I didn’t think it would cost that much” fund.

Here is my breakdown:

  1. Transportation: Planes, trains, and automobiles
  2. Boats, ferries, and even what it would cost to rent a bicycle
  3. Lodging – I use VRBO.com, Travelocity.com, and Tripadvisor.com to start my search for good deals
  4. Food – Eating out, items for cooking meals, alcohol, and snacks
  5. Events and activities
  6. Souvenirs
  7. The forgotten things: tipping; added cost of food in touristy areas (bottled water at a museum can cost up to $5); Laundromats; the item I checked off my list but didn’t really pack (a toothbrush, shampoo, hairbrush)
  8. And finally the added 20 percent “oh crap” fund

Transportation is at the top of my list because it will dictate what I have left for the rest of the items on the above list. There have been trips that transportation took so much out of the budget that eating was going to have to be crackers with catsup and water. Who said you can’t lose weight on a trip?

I covered the monetary budget, but there is another budget that is just as important to consider: the time budget. Remember, this is supposed to be a vacation or a special occasion. Try to avoid the trap of “we have to do everything because there is a possibility we will never come back here.” I have made that mistake on several trips and have regretted it. I remember coming back to work thinking I needed a vacation from my vacation. Don’t spread yourself too thin and take the time to enjoy the folks you are with and your surroundings.

Michael Altshuler

So, whether you’re planning a trip to Chicago or anywhere else, don’t forget the why you want to go there, and the rest of the planning will come together like Prince Charming putting on Cinderella’s shoe.