Now, a vacation with me isn’t really a kick-back and relax event, in fact when we got back from New York a few years ago, Jonathan and I both needed to take a few day to do nothing. I was worried that my trip planning might be too much for the Holtster, but he hung in there like a pro and we had an absolutely perfect trip. In fact, there wasn’t a single national lampoons moment the whole time, I of course attribute this to my preparation, Jonathan thinks I made some deal with the devil - actually, we have been abundantly blessed with the opportunity to go on vacations and do fun things, with wonderful weather and a (near) glitch free trip.
As soon as Jonathan gave the green-light I began planning. I found some used travel books on Amazon for pretty cheap and actually found a “kids” guide to Chicago for Holt with a little fold out map in the back. When his travel guide came in we read it and unfolded the map to locate all the sights we were going to see. In the few days leading up to the trip, Holt would unfold the map and walk around the house spouting off directions like a mini-me. “You take a left here, and then go straight, and then we get to the airport, and then get on a plane, and then fly to Chicago, and then take a right and then a left and we’ll be at the Chicago Hotel.” I wanted Holt to get excited about the trip (beyond the plane and train rides) and I know from trips I took with the Culpeppers that the more I knew about a place before hand the more I would get out of it and remember, so I found some children’s books about Chicago. Holt especially loved the comic book on the Great Chicago fire and “The Dragon of Navy Pier,” about Charlie the carousel dragon who comes to life to explore Navy Pier and watch the fireworks (once I convinced Holt that there wasn’t a real fire breathing dragon on navy Pier his excitement for the trip and the book returned). A quick funny story about my book selections. I was on Amazon searching for some books on Chicago for kids and Amazon recommended “Let’s Go to Chicago.” I read several reviews and there were several recommendations that went a little something like, this is the perfect book to get kids excited about Chicago, and this book really prepared our kids for sights like the museums and navy pier, etc. That all sounded fine and dandy to me so I ordered a used copy and eagerly awaited Holt’s library addition. When it came I flipped though the pictures, they looked great but we were in a rush to get somewhere, so I tossed it on Holt’s bed to read that night. Well, we all pile into bed that night, prepared to read Holt’s new books, and I begin reading about Travis and Jessie’s first trip to Chicago when the story takes an unexpected turn and goes into a description about how it is the boys first family trip since their parent’s divorce and their mom’s nervousness about single parenthood, etc. I was a) very glad that Holt’s reading is still limited to sounding out one syllable words and b) pretty unhappy with the amazon reviewers. I don’t have a problem with the topic really, but I need to be prepared for this, as we’ve never had the occasion to talk about divorce with Holt. Yes we shelter, don’t judge. The pictures were great, but the story was a little disjointed as anytime the D word or anything related came up we just skipped. Holt did enjoy our version (we had to read it several times) and it did get him excited about the museums, and once we were there he would reference Travis and Jessie and that this was when they did x,y,z, so it all turned out fine in the end. I have since added an appropriate review as a notice to parents.
Holt's tour book that was well worn before the trip ever began. His bags were packed and he was ready to go on Wednesday night. I thought we would never get him to bed.Our flight to Chicago left Jackson at 6:15 on Friday morning, so we drove down to Jackson Thursday after work and stayed at a hotel minutes from the airport, which still meant getting up at 4:30. When we left on Thursday, we stopped to get gas and Holt and I went in to get drinks for the road. I being the good mother that I am said no to soft drink propositions and encouraged juice or milk (why oh why did I pick that day to try being a semi-health conscious mother). Well, Holt picks out Muscle Milk, which I assume was just chocolate milk dressed up in a fancy marketing outfit. I was wrong. It is in fact a disgusting protein and “energy infused” non-milk based shake. Jonathan gave me a very hard time for allowing Holt some muscle-builder shake, but I decided to be stubborn and let Holt have it anyway. Well, two sips in, Holt complains that he doesn’t like it, tries to set it in the cupholder and the chocolate milk substitute concoction spills all over, under, and between the seat. We stopped, mopped up the non-milk and continued on our way. We ate dinner, swam in the hotel pool (eh) and then hit the hay.
We waited until the latest possible moment to wake Holt up to leave for the airport, but as soon as we told him it was time to go he was up and asking questions. Jonathan and Holt went on to the car, while I waited to speak to the hotel desk-clerk (there may have been a bit of a kerfuffle over credit cards and Expedia that I had to handle - Jonathan was quite proud). Apparently on the way to the car Holt and Jonathan had a funny little conversation:Holt - “Is it morning time”
Jonathan - “Yes sir”
Holt - “Dad, why do they call it morning if it’s still nighttime?”
Jonathan ... Stumped
Holt, after thinking for a moment - “Are you sure Chicago is open at night?”
We got to the airport and found a very long line for security, that only got longer. For a moment I thought we weren’t going to make it on the plane thanks to terrible security management, but we did and off we went. Jonathan and Holt took a little nap on the plane and we were fresh as daisies when we landed at Midway. Right off the bat the trip was made for Holt, as we got to ride the train from the airport to the station around the block from the hotel. We stayed at the Hilton Chicago, which has played vacation residence to every president since FDR (at least according to Frommers).

They were both sleeping like babies, I thought I was going to have to wake them up to get them to stop snoring.
On the Orange. Holt had a great time counting down our stops and listening for the conductor to say "Roosevelt."
Holt earned his keep as our little photographer, and his skills improved greatly each day.
We ate a delicious breakfast at the Eleven City Diner and then caught the bus to the Museum of Science and Industry. We spent hours there, it was amazing, although my favorite part was watching Holt and Jonathan hopping down the stairs together.
Holt wanted to know the names of each kind of plane there, he just didn't like us reading the answers to him, he wanted us to just know so we may have made up some names, there was so much to see what are a few made up plane names?



The U-boat exhibit was fantastic and the tour was amazing. We are now back into our WWII phase and asking questions about that bad ol' Adolph Hitler.
We then caught another bus, and Holt caught a cat-nap, to the Field Museum where we had to see “Sue” the most complete Tyrannosaurus Rex ever found (so we learned from our tour book and the Divorce book), Jonathan and I were slightly underwhelmed but Jonathan was quite impressed. I am a planner, so before we left I had a three day itinerary complete with bus routes, time allotments for each sight, and all our tickets. I also got citypasses ahead of time. We didn’t have to wait in any lines and with citypasses we got upgrades at each museum (as though avoiding lines wasn’t perk enough) and it saved us a good bit of money overall. The best of these, was at the Field Museum where we got to do “a bugs view” complete with shrinking chamber (Holt may always think that he was actually shrunk as a child) and size recomobulator (my term not the museums).
Holt was a big fan of pushing buttons. Fortunately, there were buttons aplenty at the various museums.

We went back to the hotel to freshen up before a dinner at the Drake hotel. The Drake is like the Peabody of Chicago. We went to the Coq D’or (we caught our only cab of the trip for the ride there since it was raining buckets when we left the hotel). Where we had a wonderful meal and Holt was incredibly well-behaved. The Coq D’or was the very first bar in Chicago to “officially” re-open after prohibition was repealed. I got on urbanspoon.com to read reviews and look at the menu and there was a reviewer complaining that there was a family with young kids in there one night, I am not sure if it was the menu or the hopes of offending some yuppie that made me add it to our plans, but I am glad we did because it was delicious.

After stuffing ourselves there, we walked down Michigan Avenue and the Magnificent Mile, past the water tower and pumping station that we had read so much about in Holt’s book on the Great Chicago Fire. I think Holt enjoyed seeing them and talking about the fire and “Mrs. O’Leary’s Cow.”
The pumping station ^ and the water tower v
We then made our way, after a desperate, and thankfully successful, bathroom search (thank you John Hancock building) to Millennium Park to see Cloudgate / “The Bean.” Holt and I had a great time playing chase around the sculpture and being silly in the park, that is until Holt reached back, slapped me on the thigh and said “come on big juicy mama let’s go swimming!” referring to the hotel swimming pool. We caught another bus back to the hotel while I evaluated my self image, reluctantly (on big-juicy mama’s part) donned swimsuits and swam the 30 minutes until the pool closed. We all passed out as soon as our heads hit the pillow and allowed visions of hotdogs and baseballs to dance in our heads.
Holt and his "big juicy mama"




























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