Pre-Chicago Trip

It has been a few months since my last travel blog. Today, I am preparing for my Chicago trip with the company of two wonderful girl friends, "Lily" and Veronica. None of us have been to Chicago before and thought it was a great city to visit for 4 days and 3 nights. To prepare for the trip we set aside a budget and were verbal about our expenses. I was open to spend an "x" amount of money and not have to stay in hostels and eat hot dogs. The budget for the Lily and Veronica were the same. We also tackled what we wanted out of our trip: 1) Museum visit, 2) City tour, 3) Hancock Observatory, 4) Second City Imrov, 5) Formal and Upper class dinning experience, and 6) SHOPPING!

I am known for my expert packing skills. I spent 3 weeks travelling by train with a backpack of electronics and a duffel bag of clothes that could be worn for cold snowy weather and warm beach weather. After all the flying I've done, I have learned to pack light and efficiently. This trip is no different. I will be packing 4 outfits for our day out, 1 pair of pjs, 1 pair of workout clothes, 1 evening dress, 1 evening outfit, 1 blazer, 1 jacket, 1 umbrella, 2 pairs of shoes, 2 pairs of flip flops, 4 pairs of under garments, and my personal toiletries. There should be enough room for gifts and souvenirs.

Here is how I pack:

1) I lay out want I want to bring.

Shoes & umbrella

PJs and Workout clothes

Day and Night outfits

All-Weather Jacket

2) I pack shoes first because they are the heaviest. I also throw a bag on top of the shoes to prevent them from dirtying the rest of my clothes.

3) Then, I layout all my shirts/tops and stack them on top of each other. I fold the sides in to make it narrow.

4) Then, I roll from top to bottom. I end up with a roll. Add to suitcase.

5) Next, I stack my pjs and work out clothes and roll them up. Add to suitcase.

6) I roll pants/bottoms individually and add to suitcase.

7) I then add my personal toiletries and make up bag.

8) Now for the 3rd level, I add easily accessible jacket/blazer, clutch, and umbrella.

That's all it takes. This will be my carry-on along with a cross-body bag to carry my wallet and phone.

I will be leaving for SFO tonight. My flight out is a red eye at midnight. It was cheaper for me to fly into Milwaukee than it was to fly into either airports in Chicago; $200 cheaper. From Milwaukee I have several options to get into Chicago: 1) Amtrak train or 2) shuttle service. I chose option 2 which would cost me $28. I reserved a seat for pick up at 11AM from Milwaukee Airport and drop off at O'Hare Airport in Chicago. From there I can catch the subway to meet up with Lily and Veronica who are both arriving together at Midway Airport in Chicago. Lily purchased a 3 day Chicago subway pass for the 3 of us. She got the deal on Groupon and it activates when you first use it. We'll see how much use we will get out of it.

Well, I will blog more tomorrow. See you then!