Background
So, last year for Christmas we decided to give the gift of a short vacation to my mother in law for a couple reasons. 1) I had some frequent flyer miles that were about to expire, but wouldn't get us very far. 2) We hadn't yet taken our son on a plane and felt like we should, but were pretty nervous about it and thought an extra pair of hands would be helpful. 3) She is one of those ridiculously hard to shop for people, so we thought the gift of time together would be something she would appreciate. 4) We wanted to try out the idea of traveling with family so that we got to both see family and new places, and thought this would be a good first try.
Once we settled on the idea of travelling to a city for a short vacation, we pretty quickly settled on the idea of Chicago because it was on a short list of cities we could get to on a nonstop flight under 2 hours that looked like it had a bunch of interesting things to do. We originally planned to go in May, which would've been a nice time to be there - but had a couple conflicts so we rescheduled for October hoping it would be better time and the weather would still be ok. Then, after stressing about this for over 10 months - the trip finally occurred.
Airports & Baggage
The thing I was most stressed out about was the actual travelling part - having everything we needed, but not too much so that we could get through security and on the plane. We decided to check a couple bags so that we wouldn't have to worry about getting them through the airport and finding overhead space - which was good - but it didn't solve the problem of getting the bags to and from the airport itself. So with a travel crib, 2 big checked bags, plus the stroller and a couple carry on bags - we had way too much stuff. Getting out of the airport, onto the subway, and into the hotel was a seriously unpleasant endeavor. Getting through the airport wasn't actually bad since most things were checked and we only had one larger bag that needed overhead space. We opted not to bring a car seat, which was super helpful, but meant that we couldn't use any cars on the trip and were reliant on the subway or our feet to get around. Lesson learned - get everyone into one checked bag and have adults pack as lightly as possible.
Airplanes
Once we were actually on the plane - things went surprisingly well. The kid was super fascinated by everything and not at all interested in napping, despite the fact that the plane was planned for exactly his nap time - so he spent the flight staring out the window, looking at books, eating small snacks when landing and taking off, and putting stickers all over his dad. On the flight back, he fell asleep at the gate and stayed asleep for most of the flight without noticing. For this part - I'm glad we brought a lot of stuff - from snacks to books, blankets, the whole shebang was in his diaper bag. We also got lucky and had an empty seat between us on the way there, but not on the way back - obviously, having an empty seat is helpful but turned out not to be critical, since he wanted to sit in my lap and watch the window most of the time anyway, or stood on the floor between our legs.
tip: bring stickers. buy a beer.
One of my worries was where to stay - since the kid wakes up early and goes to sleep early, which is not super convenient on a vacation. Since my MIL was travelling with us, we debated getting 2 hotel rooms, but decided to book an entire apartment through AirBnB for about the same price. It was our first experience with AirBnb, but it worked out great. Having an entire apartment with two bedrooms meant that there was a living room for him to play in the morning without waking everyone up, and at the end of the day - a place for us to hang out and watch tv without keeping up him. The kitchen was perfect for making him breakfast or having dessert and wine at night. I think having our own apartment/house was a huge success and definitely a strong recommendation for anyone traveling with small kids. There was even an indoor swimming pool that was great when the weather was crappy, and we were stuck inside.
his favorite corner of the apartment - floor to ceiling windows all around.
So the reason we wanted to go to a city was to test out our ability to sightsee with a kid; we know we could take a vacation to the beach and it would work out - the question was how to make city travelling work. So we lined up a couple touristy things to do with a rough plan to do something every day in the morning before his nap. We tried to strike a balance between things we would enjoy and things he would enjoy - and spent as much time as possible outside. One day, we walked around Millennium Park and saw the huge Buckingham Fountain (he's a huge fan of fountains and people watching). The next day, we walked along the river and out to Navy Pier. The last day we took a boat cruise of the lake and Chicago River, which he was also super excited about. In general, all of those outdoor, sightseeing activities worked out great - as long as he got a few opportunities to run around and stretch out his legs. We watched the weather forecasts closely, and when the weather turned rainy and cold, we spent some time in our indoor swimming pool. Definitely critical to have a couple options for each day that we could pick between based on the weather and everyone's interests.
trying hard to get into the Buckingham Fountain
very excited to touch the big reflective bean at Millennium Park
excited but getting tired on the boat tour of Lake Michigan
Museums
We only tried one museum while we were there - the Field Museum, which is a natural history museum. I wanted to go to the Art Institute, but was afraid that he would be too loud. He would have liked to go to the Children's museum or aquarium, but we weren't super excited about those options - so this was our compromise. I think it was a bit of a mistake - it ended up being a place that none of us really were excited about. We would try to read the exhibits, but get pulled away by him too quickly. He would see an occasional button and get really excited to press it - only to have a crusty old archaeologist start explaining history to him. Maybe in the future we would either skip museums altogether, or split up and let an adult go to the museum of their preference while the other adult watches the kid or something.
Restaurants
We ate out a lot. For lunch we generally picked up something on the way back from our excursion to eat in the apartment, but for dinner we went to a different restaurant every night. We used yelp to find good ones that were on the casual to loud side and went at about 6 pm each night. My MIL said that we should have high expectations, but be flexible and prepared - and that was exactly what worked. As soon as we sat down, we ordered food for him and brought additional snacks to keep him occupied. Once he was done eating, he would sit in one of our laps to play with a toy or book or watch a video on our phone. If he got loud, one of us would take him outside for a quick walk around the block. Having back up plans allowed us to eat mostly relaxing (although quicker than normal) meals, in a couple really nice restaurants. It made me think that we've been too cautious about taking him out and should try more.
one of many lovely sunrises I got to see
Conclusions
So - this was definitely not a relaxing vacation, but I'm glad we did it. I feel like we learned a lot about travelling with him, and are ready now to go for a slightly longer trip somewhere. I can see how travelling, like going to restaurants, is something a lot of families with small kids would just avoid - but it feels like an important thing to do, so I'm glad we gave it a try.
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