Chicago May 2015

As previously mentioned, the California trip did not exactly go as planned.  We still were facing a trans-Atlantic flight to Italy in September and did not want that to be James’s first time on a plane.  Chicago was the perfect solution.

Several airlines fly non-stop to Chicago, and the flight is only about two hours.  Plus, flights were dirt cheap in May.  We booked on American for $105 round trip all in.  United had some flights even cheaper than that, but we missed them by the time we had plans nailed down.  This time, we went with three economy seats because first class was a lot more expensive.

James did pretty well on the flights.  He got a little antsy, but we broke out something he doesn’t really get at home – the Ipad.  That settled him.  He eventually fell asleep in both directions for about half of the flight.  The turbulence seemed to help with sleep; we were probably the only people on the plane hoping for turbulence.

DSC01060-2 DSC01061


We debated extensively on our options…Carry on a car seat, check a car seat, take trains, or just chance it on a cab without a car seat.  We did not feel comfortable holding James on a 45 minute car ride…maybe for a couple minutes within downtown, but not that long of a distance.  Lugging a car seat through the airport would be a pain, but we’d do it if necessary.  I thought it might help James sleep on the plane, but Alyce didn’t think it would make much of a difference.  So, our preference was to avoid bring a car seat if possible.

Catching the train to downtown Chicago was an option, but we ultimately decided against it.  We were checking two bags and would have had to walk a little way once we got to downtown.  The prospect of lugging two checked bags, a baby, a stroller, and his diaper bag out of a crowded subway did not appeal to us.

Fortunately, we found several cars for hire that offered car service with a car seat already in the car.  We used Ride in Bliss and were pleased with them.  They were there waiting for us, provided a very nice/clean ride for us, and the car seat was in good shape.  It cost about $80 one way (taxes/tip included)—for reference, a taxi cost about $50 one way the last time we came to Chicago.  That premium was well worth it to us.  We did not have to deal with a car seat and were able to take our time loading James into the car and getting settled.


We stayed at the Langham in a club room.  The rate was more than I usually like to spend on a hotel, but it definitely worked out for the best.

First off, we saved a lot by booking an ABA rate.  Even if you are not a lawyer, you can sign up as a non-lawyer member “associate” member.  One night in the club lounge at the Langham would save you about what the annual dues are.

We enjoy hotel club lounges as much as the next guy, but we had never actually paid for access to this point.  Why now?  The thought was that we could get a club room on the club floor close to the club (we did).  When James took one of his two naps a day or when he went to bed at 7:30, we could go walk to the club lounge and enjoy ourselves rather than sitting silently in the hotel room while he slept….and that is exactly how it worked out.  Plus, the club was really nice.

Breakfast consisted of several hot options – bacon, eggs, sausage, corned beef hash, French toast, etc.  There was also round the clock coffee, soft drinks, and snack.  There was also an afternoon tea service with scones and sandwiches that we ate several times.

Happy hour/evening food service was plenty enough to replace dinner (as we did a couple nights).  The liquor/beer selection had many good options.  There were also several different types of wine available, but none of them were particularly exciting.  If I had one complaint about the club, it was that it could use an improved wine selection.  Most everyone in the lounge was drinking wine, so I can understand why upgrading the selection would be expensive.

The room itself was very, very nice.  The hotel is pretty new, so everything is still “fresh.”  I’d put it up there with any of the rooms we stayed at.

DSC_2910 DSC_2908 DSC_2907 DSC_2906 DSC01078 DSC01077 DSC_2915 DSC_2911DSC01073


I had previously mentioned getting our money’s worth out of the club lounge…Well, we only purchased one meal the three days we were in Chicago—deep dish pizza at Lou Malnati’s.  We ate there the first day, and James was quite the wild man.  So with the variety of options offered in the club, we found it easier to just stay there and eat the rest of the nights.  We thoroughly enjoyed Lou Malnati’s, just as we did our previous Chicago trip.

DSC_2928 DSC_2932

For activities, we did a lot of walking.  James is just about always happy in his stroller walking around, so we stuck with that.  Plus the weather the first two days was beautiful.  The last day, it was cloudy and pretty cool. DSC_3012 DSC_3018 DSC_3008 DSC_3005 DSC_2920 DSC_2921 DSC_2919 DSC01063-2

We walked around Navy Pier.  It was being renovated on one side, so it was crowded at spots.

DSC_2972 DSC_2968 DSC_2965 DSC_2963 DSC_2960 DSC_2950 DSC_2944

We walked back to the Lincoln Park Zoo.  There were plenty of people there with the nice weather.  James was still a little too young to get too excited about the animals there, but he did point at a couple of them and seemed to like it.


We also walked through Millenium Park and to Buckingham Fountain, which we missed being turned on by one day.  And we of course walked down Michigan Ave. a couple times.

DSC_3003 DSC_2999 DSC_3001 DSC_2992 DSC_2991 DSC_2988 DSC_2981

Concluding Thoughts

This was a very quick trip—not to mention different than our previous trips.  We were in Chicago for 3 days.  With the quick flight, we got a full day in on the day we arrived.  Same as before, we thoroughly enjoyed Chicago.

Most notably, it was our first trip with James.  He had his moments but did well overall.  He was at an age where he wanted to crawl around and explore, but he was not eating the same food as us.  This led to him being quite antsy at restaurants.  As a result, we did not eat out as much as I had originally planned – but that was fine with the options at the club lounge.

Speaking of which, the club lounge was a life saver.  It allowed us to have some time to enjoy ourselves while James was napping and in the evening after he went to sleep.  I had this in mind when planning our stops in Italy.  While we’re not staying in hotels/club lounges, we will be staying at multi-room vacation rentals.  I think this is for the best because we would have been very bored sitting quietly in a hotel room while James napped/slept.

Overall, I’m definitely glad that we were able to get on the road with James before leaving the country for two weeks.  It helped making decisions while planning for Italy.  I think some things will be easier when we go.  James now eats most of the things we do, which helps keep him entertained in restaurants (at least moreso than before).  He is also off of bottles/formula and now drinks milk from sippy cups.  Hopefully everything will go smoothly – as it mostly did in Chicago.


Leave a Reply

Your email address will not be published. Required fields are marked *