Heading to the Windy City

Debs and I will be celebrating our two year wedding anniversary this month! Its hard to believe that 1) we have been together for over 8 years now, and 2) that we are already celebrating our two year anniversary! Last year we bought the house, so we ended up not doing much but going to Williamsburg for a long day trip (pics here and here).

This year, we are doing something MUCH different.  Originally we were going to Las Vegas again, and we found a GREAT deal (staying on the strip and flights out there costing around $1000). But by the time we got around to booking, the price had jumped up $500! We also tried scheduling for a few weeks after (my parents will be out there for a conference for my stepdad), but we have a wedding and some other things going on back here in RVA.

Both of us really like big cities, and thought it would be nice to try something different, like Chicago, NYC, or Boston.  After looking around, we decided on Chicago. Its big and fun, but not as busy as NYC. There are also some cool events coming, including something called ART Chicago we may check out while there. Im excited to also take some cool city-scape shots with our XTi to help fill our house up with photography.

The best thing about this? Hotwire.com. I have only used them once before, a LONG time ago. We had been looking elsewhere, but decided to check out hotwire after a recent commercial I saw, advertising rates in Chicago as low as $79.99. After clicking through the site, I found a ‘4 star recommended’ hotel near the airport (even though we will be driving). It was listed at only $75 a night! After booking, we find out that its the Hilton at the Airport, and I start doing some research on reviews. This hotel had many perfect reviews, including perfect customer service and support. A lot of people also boasted that while being at the airport, they never really heard planes, and that some of the views from the place were amazing! Finally, I see what some of these people were paying – $250 to $300 a night?!?!

So the next few weeks are going to be filled with researching the city, packing bags, and planning the trip. I already set up a ‘schedule’ on Google Docs that Debs and I will use to kinda plan out what we would like to do.

Oddly enough, with my current occupation, its interesting to see how these cities promote traffic and visitors to their sites. I have found that Chicago.com (who is a member of the associated cities like us, and the only one other than NYC that get more traffic than we do) and ChooseChicago.com (the CVB site for the region) have been GREAT resources in learning about the area. Now if I could find any specific Chicago area blogs!

Listening To: ‘The Scientist’ by coldplay


3 thoughts on “Heading to the Windy City

  1. Hi!

    Not to be a nosey poster, but I currently work at the Affinia Hotel in downtown Chicago, and I came across your blog through my Google alerts for “Chicago Hotels.” Typically I use this to see what my competitors are doing, but I noticed your posting and thought I would offer some friendly advice.

    If you are really interested in experiencing Chicago, it may worry you to know that the trip from the Airport to downtown Chicago can take anywhere from 30-45 minutes (not accounting for the crazy traffic on the roads you can encounter). There are public transportation options, like the El, but then you may still experience quite a trip to your downtown destination.

    I would recommend booking a hotel on the North End of Michigan Avenue so you are close to the action.

    I hope this helps!

    A Friendly Chicagoin

  2. Erin thanks for stopping by! I do know about the delay. I will be driving from Richmond up there. While not a big fan of staying in traffic, I dont mind the commute all that much. May actually check out the El as well. I did a bit of looking around for hotels, but I did not come across yours.

  3. Congrats on 2 years! It seems like the wedding was just yesterday, I hope you all have a great time.

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