Planning a 6 Day, 5 Night Trip to Chicago for Two with $2,000

My class took a trip to Chicago when we were in eighth grade. We visited some great places, and Chicago left a lasting impression on me. I knew that one day I would go back to Chicago to go sightseeing. So, when my and my fiance's one-year anniversary rolled around, I knew that a surprise trip to Chicago was the perfect gift for both of us.

I wanted us to be able to go away for a decent amount of time because I knew that trying to pack in all the sightseeing in a weekend would not allow us to have the relaxing vacation I had in mind. So, I set a budget of $2,000, including spending money, and then starting browsing travel sights for deals that would make it possible for us to enjoy 6 days and 5 nights in Chicago.

I knew that staying downtown on our budget was not going to be possible to I figured the best way to go about things was to look for hotels within an hour of downtown that cost considerably less per night.

I turned to Hotwire.com to find the best deal I could within a reasonable distance of downtown Chicago. An Extended Stay America in Downers Grove, Illinois was where we ended up staying for only $32 a night. So, in total we ended up paying $181.84, including tax, for a 5 night stay about 40 minutes to an hour outside of Chicago. The next thing I needed to figure out what how to get there.

I knew that my old station wagon was not going to make it to Chicago, around Chicago, and back, so I had to find a rental car. I knew there was an enterprise right around the corner from our apartment so I decided that that would probably be the easiest place to rent from.

I visited their website, selected the cheapest option, and added insurance to my rental since I wasn't sure how crazy Chicago driving might be. The total for my 6 day rental of an economy car was $199.20, however, at the time I had to put down $400 dollars as a security deposit on the car, the remainder of which would be refunded to my bank account after my rental fees were deducted from that amount.

So, for upfront travel expenses I shelled out $581.84, $200.80 of which I would get back once I returned the rental car. That left $1418.20 for meals, sight seeing, gas, parking, and shopping.

I knew that I wanted to revisit some of the sights that I visited as an eighth grader, and I also wanted to add some new sights to the list. Here are the sights we visited and the amount they cost:

Brookfield Zoo $10.00 each
Shedd Aquarium $23.00 each
Adler Planetarium $10.00 each
Museum of Science and Industry $11.00 each
DuSable Museum of African American History $3.00 each
Art Institute of Chicago $12.00 each

So, in total we spend $138 on sight seeing around Chicago. My favorite sights were definitely the DuSable Museum of African American History because it was great to see exhibits on people I was learning about in my Harlem Renaissance class. I also really enjoyed the Brookfield Zoo, we spent about an hour watching gorillas, amazed at how human they acted. The rest of the sights were great too, but these two were my favorites.

After sight seeing expenses we were left with $600.00 each to spend on food and shopping after setting aside money for gas.

We ate at random restaurants that we thought looked interesting, making sure to pay attention to how much our meals cost before ordering them, which helped to keep our food bill down. One place that I do remember eating at on our trip was this cute little diner called the Artist Snack Shack, I believe that is what it was called. What really struck me about this cute little restaurant was the fact that they had cocktails on their menu right alongside their home-cooking inspired entrees.

We did do some shopping while in Chicago, but not a whole lot. We bought some souvenirs at the Hershey store and such, other than that, most of our shopping was shopping that we could have done in Michigan.

Overall we had a great trip that was really relaxing and full of experiencing Chicago. We didn't do any extravagant shopping like many may plan to do when they go to Chicago, but that just isn't our style. We ate at some really nice restaurants as well as at some fast food restaurants.

The key to planning a long vacation that allows you some luxurious experiences is to cut costs in areas that don't really matter that much to you, which will allow you to get in those experiences that do matter to you.

We didn't eat out at really fancy restaurants every night or make purchases at Guess, but we did get to have a half hour horse drawn carriage ride through downtown. We didn't stay in a fancy five star hotel downtown, but we got to stay longer and see many different sights without being rushed.

If I had to do it all over again, I would do it exactly the same. I loved every minute of our trip, and if you find yourself going to Chicago, let me highly recommend a horse-drawn carriage ride.