The Windy City

I've decided to start documenting some of our past trips while waiting for the next few to arrive.

So, without further ado, here is a recap of our trip to Chicago in June 2011.

Last year, J & I decided we'd like to start trying to visit one new city every year. When I had a work trip out to Chicago, it was the perfect opportunity to fly J out and stay for the weekend.

Have you ever used Priceline's negotiator? We hadn't either before this trip. Well, actually this is the only time we've used it. But still, it was fun! And pretty nerve-wracking. You basically choose an area of the city you'd like to stay in, the number of stars the hotel should be, and how much you're willing to spend. We started out cheap. Real cheap. But obviously wanted to stay close to downtown if possible, and in a decent hotel, so we went through a good amount of rejections. Can't win them all...

You're given one opportunity every 24 hours (per email address). Of course, we used both of our email addresses! But it did take sometime, and we did end up going up in our bid. But hey, it was worth it. We were able to get a room at the Club Quarters in Chicago. Which was there -->


It was a great location for us. We walked EVERYWHERE. Seriously. I was on a mission to make the most of our weekend and see as much of the city as we could without breaking the bank.

So we cheaped out on some things, like breakfast at Starbucks & almost no cabs, and spent $$ on others, like a tour at the top of Willis Tower (formerly the Sears Tower) & a tour of Wrigley Field.

View at the top of Willis Tower

Yes, those are the ROOFS of other buildings below us

Imagine my legs shaking uncontrollably in these photos at Willis Tower. I don't care how "safe" it is to stand on the clear overhang, it is freaking scary. I don't think either of us is breathing in these photos. Those are nervous smiles.

We then headed over to the water to see the "bean" and walk the Magnificent Mile.

View from the Magnificent Mile

And then it was time for lunch at Portillo's. Have you heard of it? We were told by a former co-worker from Chicago that it was a MUST. Chicago is known for its Italian beef subs. Glad I tried it but definitely do not need to eat another.

Bevies were clearly needed at some point. :) Can you guess whose is who's??

Sunday we made our way up to Wrigley Field.

 A trip to the Goose Island Beer Garden to beat the heat. :)

Yes, this is a photo of iced tea. Not weird. Have you had Argo Tea? J & I both LOVED their strawberry green iced tea lattes. So good. We don't have Argo Tea here in Boston. :(

And that was it! We made our way to the airport via Chicago's subway system (yep, saving those dolla's!) Sunday night and were back in Boston to work Monday.

Oh, and OF COURSE we went out for deep dish pizza! Friday night when we met up in the city we headed to Lou Malnati's for some pizza. And it was deeelish. No photo though. :( Damn. I'll get better at this, I promise.

But Chicago was a lot of fun! I'd highly recommend it for a weekend getaway.