Chicago-Not my kind of town.

Chicago-Not my kind of town.

As Sinatra crooned “This is my kind of town Chicago is.” We used to feel this way. I mean any city that has a whole section of town devoted steak houses can’t be bad, right? There are museums, wonderful shopping and great urban parks, but our trip there with our 18 month old was a disaster.

The Bean

The Bean at Millennium Park

I should give some context before I tell you why I loathed Chicago. We were in a strange stage of life.  We had rented out our house and making our way across the country and back in 6 months. About one month in Clark lost his biggest account which put a serious pinch in our budget. We were waiting on a big check and it was being delayed. Our money was not running out…we were broke. We had our prepaid hotel, the Marriott on Magnificent Mile. This in the past has been a great hotel for us. We love the location, right on the main strip, blocks away from Millennium Park  and the Art Institute of Chicago (Remember that scene from Ferris Bueller’s Day Off were they run through the museum, this is the place) and few dollar taxi ride to almost anywhere else.

We were finishing up the first leg of the trip and were about to spend 3 weeks with Clark’s parents where we could relax and reevaluate our situation. We were out of money and out of energy for traveling. Clark had a seminar to attend and business meetings in Chicago so we couldn’t cancel. Trapped. That is the perfect word to describe my time here.


Our  time started out with a 4 am wakeup in Cedar Rapids and a 3 hour drive to Chicago to get Clark to his conference by 8am. We couldn’t check in that early so I took the Jackson to McDonald’s and got some breakfast. I should have known it was a bad sign…Jackson hated the McDonald’s. I have never had him misbehave as badly as he did there. I carried him out of there kicking and screaming and put him back in the car. $5 and 15 minutes down. 8:15 just 3:45 until early check in!

By 10 am I couldn’t wait any longer. Not wanting to pay to park our car so we could walk to a park, I decided to try to get an early early check in. I drove up to the hotel in our blue H3 Hummer. It was loaded!! I mean there wasn’t an empty space in the car, we had a huge roofbox and huge stroller strapped to the roof. We had the stroller tied on with orange rope that we had from Tahoe. The orange cords went from the roof, over the windshield and hood and tied off on the front bumper. We were behind a black Mercedes in the valet and I felt like the Clampetts pulling into Beverly Hills.

Millennium Park Fountain

After unloading half our car on the curb at the valet and having who knows how many toys and partially eaten food remnants fall out I loaded up the bellman’s cart and handed over the keys to the car. I was hoping that they could find a place to park as our loaded car was too tall for the garage. There problem now. I held my breath and walked into registration to beg and plead for a room. They did it, no problem! I was so thankful.

While the hotel was nice and the location was awesome, it wasn’t a kid hotel. There was no pool, the lobby was huge and suited to corporate happy hour and not so much a toddler wanting to play. The rooms were nicely appointed and had sleek furniture, but they were small and not so sound proof. We had 4 nights here and I was already feeling trapped.

Clark was at his conference all day, so after I set up the pack and play in the worst possible, but only available spot, in the hallway blocking the door to the bathroom and the door out of the room, Jackson took a nap and so did I. Normally Jackson is an awesome sleeper. He has always been on a good nap routine and slept through night no problem. Not here! 45 minute nap and Jackson and I were off to see the town. Did I mention it was really cold and windy?

Fun at Millennium Park

Fun at Millennium Park

I don’t know what I did the rest of the day or the subsequent days. We spent a lot of time Millennium park and walking the city. Jackson can be happy almost anywhere and especially loved Millennium Park. It was free and I felt like we a part of Chicago. When Clark wasn’t working we went out together and it was better. We ate on the cheap, split small pizza for dinner and then hit up Trader Joe’s for snacks to hold us over during the day.

Feeling relieved the day was done and very excited to get a good night’s sleep we turned in early. Good thing because Jackson was up almost all night! It started at about 1 am and finally at 3:30 I couldn’t torture our neighbors any longer. I took him to the lobby and let him run around. It was completely empty and he loved it. I, on the other hand, was miserable. Just three more nights!

Then our check arrived. We were never so excited. We could finally do a few things that we had been longing to do. We booked a sitter and headed out for a nice dinner. Lawry’s Prime Rib House was our choice. Not too pricy for a steak house in Chicago yet a landmark in Chicago history. It was incredible. We loved our dinner, we enjoyed a stroll around the city and felt like a weight was lifted from our shoulders. Things got easier, but I still felt like I was just counting the hours until our departure.

The next day we checked out to the Shedd Aquarium. This was great. The Shedd is off the Millennium Mile and a bit pricy, but worth every minute and dollar. We left there and headed to Indiana to be with Clark’s parents.

Shedd Aquarium

Shedd Aquarium

This stay in Chicago was a turning point for us in our traveling lives. We learned several key things that have governed our family travel ever since:

  1. Never stay more than 3 nights in a hotel. That fourth night was torture. You can manage a few nights in a bad place, but even 3 nights is pushing it.
  2. Look for kid amenities, pool or grassy area, playground over location. Nobody can enjoy the great location if your kids are unhappy.
  3. Opt for a bigger older room over a newer smaller room. We always try to find a floor plan when booking a hotel. See if there is a closet you can put a pack n play or at least a place for the kids to sleep that doesn’t require you to hide in the bathroom!
  4. Cities are a tough place to be when you are broke. Parking is expensive, food is expensive, most attractions cost money, and generally you just feel like you are missing out on the city. Opt for beaches, forests or mountains instead of urban settings.

Don’t get me wrong. Chicago is one of the great US cities. It has so much going for it, but for us it was the perfect storm. No money, no energy for travel, Clark having to work, and weather. We will go back and it will be different. I hope you can learn from our mistake and have happy family treks!


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