Holly and I have known each other for just under 17 years. She’s going to be 37 this year and I was at her 20th birthday party. It’s been a long time. My favourite part about hanging out with Holly is how she laughs at my jokes. All of them. But, I digress.

Holly has three adorable children.

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And an amazing husband (who laughs at fewer of my jokes, but whose own jokes are way superior to my own).

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Holly and I started talking about taking a trip together, just the two of us, when she got pregnant with her third child. When he was a year old, we booked flights to go to Chicago together for a girls weekend. A LONG girls weekend. Like, five days/four nights kind of long. Did I mention that John’s an amazing husband? And that those kids are 5, 3 and one year old?

About 10 days before we were scheduled to go away, Holly had to have emergency surgery. Before the surgery we talked about cancelling the trip, or my going alone, or her husband maybe coming with me instead. Holly is a pretty determined woman, though, and she grilled her doctor about the trip and if it was possible and lo and behold, we went.

Because I’m super, um, “organized”, I had an itinerary. But because I’m flexible, I can move the things around the itinerary for weather or other reasons. Holly had a couple of restaurants she wanted to eat at, and we melded the two things together into a truly awesome trip.

We went to a Cubs game in the rain. There were some pretty nasty floods after three weeks of rain in Illinois, so not that many people went to the game. In fact, most of Chicago was shut down when we got there on Thursday.

We shopped. Side note: we both bought bras. My Canadian peeps can weep at the following info: four bras, $90. Yeah, I was pretty giddy, too. Holly actually had a tear in her eye when the first Macy’s we went to only had two that she loved in her size, but we found another Macy’s and she bought more.

We did the Art Institute. Sweet Jesus, that place is big. You’d need a few visits to actually see and absorb the whole thing, I think. We spent three hours there and barely scratched the surface.

We went to Frank Lloyd Wright’s home and studio in Oak Park, which was a truly lovely L ride from downtown. Now, I live in an urban neighbourhood where a 2000 square foot house is considered to be huge. The houses in Oak Park are ENORMOUS. Like, their front porches are bigger than the first house I owned.

We did a tour of outdoor public art, and we went up to the Skydeck of the Willis (former Sears) tower.

We ate. My god, we ate. We went to great chain restaurants and celebrity chef places (recommend: Little Goat) and this place for brunch where we ate for 90 straight minutes and couldn’t figure out how they make any money at all. I had two of my top 10 meals ever in Chicago.

The people were lovely. The food was yummy. The sights were great. The shopping was good. (Side note: Best shopping experience ever at Nordstrom. Can’t wait til they come to Ottawa.) It was so cold we needed to buy emergency sweaters. Even the pigeons were hanging out next to an eternal flame.

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