savin' and smilin'

Planning a Chicago Trip … on a Budget!

In Uncategorized on July 28, 2009 at 2:54 pm
Danny and I smiling at the Baltimore Inner Harbor last year.

Danny and I smiling at the Baltimore Inner Harbor last year.

So my boyfriend, Danny, and I are working on organizing a Chicago trip for the beginning of August. I am certainly excited, but a little worried that the cost will add up to be a little more expensive then I’m comfortable with. Therefore, I am searching for savings and watching my spending like there’s no tomorrow.

I am not quite used to buying nice things for myself. It is not that I do not have nice things because, to be completely honest, I do. I am spending four years in college without any loans, I am living in an apartment off-campus with cable and high-speed Internet — the main difference here is that my parents, lucky me (I know), pay for these things. As my boyfriend explained to me yesterday, my parents look at me as an investment for the future. They don’t expect me to pay them back or buy them lavish things (though I’m sure they would enjoy that); they simply expect me to do well in life. And I am certainly trying my very best to make them proud.

Even though my parents have been very helpful in terms of funding my education and rent, they have instilled in me the importance of saving and spending wisely.

As for Chicago, I shall be drafting a budget with Danny, no matter how much he squirms, in order to save us from throwing our savings into a one weekend trip and coming back broke as jokes. This Chicago trip is important, since we both are considering moving there after graduation, so we are planning to spoil ourselves a little, but as in everything in life, there is always a self-imposed limit. At least, there is with me.

For anyone who is interested in booking trips for less, try Orbitz or Expedia; I had luck with the latter. For now, Danny and I have already paid for a room at Sutton Place on Magnificent Mile the Gold Coast (pictured below) — a bit more expensive than I wanted, but hey, you’ve got to splurge every once in awhile.

A boat skids across the Gold Coast, Chicago. © Parker_Lewis/Flicker

A boat skids across the Gold Coast, Chicago. © Parker_Lewis/Flicker

Expedia was great because they had a 24-hour sale going on for Sutton Place, at a rate of 45% off the original price. Danny had originally booked our room at Sutton Place through another Web site, but he quickly cancelled and booked with Expedia, saving us almost $100 total.

Another tip: when booking online, make sure you can cancel. This is very important as online sales happen all the time with different sites.

Also, check out Twitter for savings on travel and tips for your trips. I know, I know — Twitter. Have you heard enough about Twitter yet? But honestly, many hotels and travel businesses have Twitter accounts, and their PR people are usually more than willing to help out with planning; you may even score a few coupons out of the deal.

Well, I shall update on this Chicago trip more later, but feel free to comment! Thanks for reading.

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  1. Try Travelzoo.com- they find all the best deals on all different websites to all different places. I just booked a trip to Vegas with my boyfriend for $270- includes flight, 4 night stay and transportation.

    Also, I live in Chicago- if you need any advice- just ask 🙂

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