J and I have been trying to decide where to go for our fall vacation. We’d been toying with the idea of going back to St. Thomas (where we went for our honeymoon seven years ago) but it was more than we wanted to spend right now (at least for the hotel we like).

We don’t get to travel a lot (due to both limited finances and limited vacation time) but when we do we prefer to fly Jet Blue if at all possible. It flies out of Hartford but only to select locations, limiting our options. (It does fly to Orlando, where my bestie lives, so that’s all sorts of awesome, and resulted in me visiting Florida three times last year.)

We usually take vacation in mid-October but this year our friends are getting married smack in the middle of the week we’d typically go. The wedding is in Boston. We decided to see where Jet Blue flies from Logan Airport – lots more options! Since we’ll already be in Boston it will only be the 2 hour drive home that sucks, not the round trip.

So we decided to go to… Chicago! We’ve been saying for years that we want to go but never seem to find our way there. This is the perfect opportunity.

But wait… there’s more. We’re also going to Madison, Wis. My sister and her husband moved there in January (from Virginia) and we haven’t been able to visit them yet. They love Madison and we can’t wait to check it out.

Halloween circa 1985-ish. I am Snow White.

At my wedding in 2005.

Getting ready for my sister’s wedding in 2008.

So here’s the plan:

Saturday – Wedding in Boston. Stay over at hotel convenient to airport.

Sunday – Fly to Chicago early in the morning. It’s a direct flight and we’ll be there at 9 am!

Sunday – Wednesday: Chicago! Enjoy some time just the two of us and explore a new city.

Wednesday: Pick up rental car and head to Wisconsin!

Wednesday – Sunday: Spend quality time with my sis, her hubby, and their two dogs. Relax. Go hiking. Eat fattening food. Check out the local vegetarian restaurant and pizza place that offers vegan cheese that I found. (I read on someone’s blog that they have a “We serve Daiya” sign on their door. Can’t remember whose blog so if it was you, thank you!)

Sunday: Flight home in mid-afternoon, then drive home from Boston. Possibly probably definitely some tears.

Can’t wait to see this girl!

My sister in 1997, the day our dog Molly came home. Molly is the puppy on the left, and her brother Jesse is on the right (a family friend adopted Jesse).

Anything we need to see/do while in Chicago? Museums, restaurants, places to run?