
We kept the girls' birthday present a secret (a trip to Chicago and the American Girl store) until the day before we left. They cleaned up on birthday presents; between the two of them they had $750 dollars spending money from us and grandparents. Grandparents should be expecting a big thank you note from the girls. We left early Friday morning.
Jack
Jack really loves his family. It's obvious he's happy when we are all together and the vacation was heaven in a 20 foot by 20 foot room. When Jack is happy, you know it. He's jumpy, he's active, he jibber-jabbers, and screams with glee (loud: Jack happy at 4AM is rough). Since we were all in a 400 square foot room, Jack had everyone he wants close together. It was exciting enough that the boy would not go to sleep on his schedule. He wanted to stay up with his sisters.
There was no flat surface in the hotel room, that Jack didn't pull everything off. If he could reach it -- it was on the floor and in his mouth. This was the fate of numerous flyers on the dresser, the alarm clock, a lamp (almost), and much to the the girls' consternation any new item they bought that was in reach was quickly in Jack's clutches if not properly placed. Monday morning he woke up a sister by pounding on her face.

Chicago was Jack's style. We forgot his stroller, critical, CRITICAL mistake. Mom and my arms are twice as big, so he was help, which he prefers. He loved to watch the cars in the city, he took the big buildings in, and he was fascianted by the "L" train. However, when it was the boy's time out, while the girls watched the American Girl doll theater, he only slept.
Madeline 
Madeline loved her birthday presents. I wrote in the birthday card the big secret -- that we were headed to Chicago, but Madeline missed this. She was so excited to be on the road, and almost the whole time laughed and joked all the way to the city. During the car trip, she kept asking, "When are we getting to Colorado?" "Chicago, Madeline, we're going to Chicago," I replied, but this never really sank in.
It was so exciting for both girls to say in a hotel room. It had a pool, but with the weather (rain) we never did swim. First we raced to the beach, and it was freezing. Madeline wanted to make a sand castle, and in classic Madeline mode, improvised using a cone from the beach to create a sand castle.
The first day we went to Navy Pier and visited the Children's Museum and other things. I wanted to ride the Ferris wheel, so we could see the city, but Madeline was a little shaken with how high the wheel would take us. Initially, there were objections, Madeline and Mom were going to find something else, but she found the courage to take the ride up and she ended up liking it enough that she wanted to ride again.
The American Girl Doll store was the most fun. She was able to see all the dolls, and for Madeline I think the funnest part is dressing like the doll, dressing up and using her imagination. So, there was sensory overload in the store.
Terra 
Terra was so happy to be with Madeline. When she came Thursday evening, Madeline was at twilight camp, and she persisted throughout the night asking, "Is it time to get Madeline, yet?" We all drove to the pick-up spot, and when Terra saw Madeline, she sprinted to her and screamed, "MADELINE!" Madeline was equally excited, they gave each other a big, huge hug.
During the car ride down, the girls made their lists, tallied up their numbers to see how much stuff they wanted, and pare that list down to what they could afford. They could not have been better in the back seat, laughing, playing their game girls, and sometimes even sleeping.
When we arrived at the beach, Terra noticed a gang of girls on a birthday party, all of whom were swimming gleefully in frigid Lake Michigan water. I wanted no part of that water, but Terra wanted in so badly. She cajoled Madeline into take a running start and jumping in the waters. This ended with both walking right up to their knees and turning around. Eventually Terra talked herself into it, and then Madeline went along.
At the AG place, Terra looked so distracted. The store has lower (period pieces), middle (photo shop, gift shop), and upper (clothes, dolls, bitty baby) levels, we visited the middle and upper levels first, but Terra didn't pick anything out, she had nothing she was claiming yet. I asked, what's the matter and she replied that she had to find
Julie's dress, but couldn't find it anywhere. Madeline was off with Mom looking at different clothes she could buy with her money, I said that once they get back, we'll check out the other levels and we haven't seen all the store. Downstairs we went and there was the dress! A noticeable relief came over Terra's face as if she was thinking, "Yes, this store is everything it could be."