Plan My Vacation For Me, Would Ya?

Stephen and I are going to Chicago for about 5 days this summer. I’m not going to tell you when we’re going because I don’t want you to break into my house and steal all of my hand-me-down furniture and our DVD/VHS combo. So we’ll just leave it at: This summer.

Here are the issues. We’ve never been to Chicago. We have about 2.5 days to do what we want, then we’ll be in a suburb of Chicago for a wedding and all the wedding festivities. So we need to FRUGALLY fit in as much fun as possible between Wednesday morning and Friday noonish. We’ll fly in on a Tuesday evening so we have a full day on Wednesday.

Here are some details. Any help, thoughts, feelings, or advice would be so very appreciated:

We’re going to go to a Cubs game one evening (not because I like the Cubs, Heavens no, but because I like baseball and want to go to Wrigley) and Stephen is interested in some sort of mob tour. We like food, but not seafood.

We’re flying via Hobby so that means we’ll fly into Midway. I have no idea what that means as far as our location goes. (I know I could look that up… and I will. But you’re so much better than Google and your advice will be so much clearer.)

I’ve been told we should rent a car. Yes? I had always imagined Chicago to be a lot like New York where people just take cabs and public transportation everywhere. Am I wrong?

I was hoping to use Expedia or one of those types of sites to book our flight and hotel. We’ll only need a hotel in Chicago for like 3 nights, then we’re heading to a suburb for two more nights. So our flight home date will be different than our check out date. Can those sites handle that? I would imagine so. Do they have people you can call to walk you through the process?

Where should we stay? What do we have to do? Where to we have to eat?

I need to download a map so I can figure out the city. So if you have recommendations, can you let me know what part of the city you’re talking about?

Thanks so much. Feel free to pass this along to any Chicagoians… Chicagans… Chicagos.. Chicago people.

(Edited to add: No, we will not be taking Jansen with us. I don’t know how I’ll be away from him for 5 days, but I’m going to try.)