Last weekend Jack and I surprised Jeff with a trip to Chicago for his 30th Birthday. It was really fun setting it all up and trying to pull it off without him finding out. I debated whether or not to bring Jack along with us and in the end decided to bring him. After spending the last couple weeks with babysitters and the changes that are in store for him once I return to work this school year, I just couldn’t bear to leave him (and I love being with him!) He really did such a good job on the trip and despite just a few planning and logistical issues with the stroller, having our little man in tow didn’t slow us down much! He really is such a good traveler.
We were total tourists and walked around and explored a ton. We were also able to see a Cubs game. It was so much fun! Jack was such a trooper despite the drizzle and humidity!
Here are some pics:
If you are heading to Chicago with a baby here are some tips:
Pack Light: We were only there for the weekend so I packed light! We also trekked all our stuff from the airport onto the train and then to our hotel. So it was worth it to not have a ton of stuff. (We did bring our pack and play, which was a struggle, but so worth it because Jack slept like a champ!)
Plan To Not Plan: The only things I had planned for the weekend were the Cubs game and for our friends to surprise Jeff on Friday night for dinner. We didn’t have reservations anywhere the rest of the time because I wasn’t sure how the days or evenings would be going with Jack. In hindsight I would have at least made a list of things to do, because even though I had some ideas, we still ended up just roaming about for a good portion of the day.
Hit The Tourist Spots Early: We were lucky to hit a lot of tourist locations early and that made managing the crowds so much easier! There was hardly anyone at the bean when we visited, which made for great pictures (it was also raining, but we didn’t mind!)
Time In The Room: Know that you will probably be spending a little more time in your room than you would if you didn’t have a baby. We tend to be on the go on our vacations and often don’t return to our hotel room once we leave for the day. We knew though that if we gave Jack some time to play in the room a little, it would pay off later in the evening, and it was true. We had a great centrally located hotel, and it also gave us the opportunity to cool off a little bit after the Cubs game- man, that humidity!
We enjoyed:
The Bean (aka Cloud Gate Sculpture)
makeeverydayOK 
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