Visiting Chicago with a Baby

I did it – I survived my Chicago trip.

For a minute there, I wasn’t sure if I was going to make it!

As I previously wrote in 2 Goofballs & a Baby…on a Plane , I had the opportunity to go to Chicago for a week-long work conference. I was looking forward to the conference – since I’m new to the world of higher education it is really good for me to meet new contacts and learn as much as possible.

Yes, Jack is wearing his “Born in the USA” onesie — I thought it might get us through security faster…

I was also looking forward to the challenge of traveling with my 5 month old baby. He’s a pretty laid back little kid, so I was curious how he’d act both on the plane and in an unfamiliar place.

Looking back on my plan of attack, I did really well. I was super prepared and had pretty much the perfect amount of everything for baby care. I even ended up with extra diapers and outfits because he didn’t pee all over them like I expected.*

Our plan of totally hogging a row of the plane worked out really well (on our departing flight). We boarded between Group A and Group B, so when we got on I went all the way to the back of the plane and we took over the row in front of the bathroom. As expected, nobody wanted to sit by a baby so we were able to keep the space to ourselves!

Since it would be super boring for me to do a play-by-play of the entire trip, here’s the best and worst of it all:

This is Lindsay and Jack showing you how hot it is outside. Well, Lindsay is making a “Chicago is hot” face, but I think Jack is just staring at her boobs.

People Suck
Reason #1: Chicago is pretty crowded and it was super hot the week that we were there too. So I’m sure that everyone wasn’t exactly in the best mood as they were traipsing along on the sidewalk. However, when you’ve got a baby in a stroller you’re pretty limited as to where you can walk since you need to get that thing up the curb’s ramp on either side of the road.

So you can just imagine my fury when I was repetitively knocked into and pushed around! It got to the point that I would just yell out “GOING FOR THE RAMP” when in a crowd of people so that I wouldn’t have to pop a wheelie to get up the curb. Probably annoying to everyone around me, but whatever, it totally worked.

Reason #2: On our return flight we were so ready to just get on the shuttle and get home. When the first shuttle to our lot filled, the representative pointed us towards another shuttle that was pulling up to the curb. So, the entire group that was left trudged over to the new shuttle. While standing in line, a lady shoved my baby (in his carseat) aside so that she could get on with her group. Yeah, she SHOVED my baby. However, at this point I was so tired that I didn’t feel like opening a can of whoopass {I know, totally out of character for me!}. I ended up sitting next to her on the ride to our car and pretty much forgetting about it once we got off to go home.**

Waiting in line to get on our “standby” flight. Which was also the time that Jack decided he NEEDED his bottle.

People Rock
Reason #1:Throughout the entire week we ran into truly nice people. The hotel staff was phenomenal, I met lots of great people at my conference and even waiters/waitresses were super accommodating for Jack. I was so incredibly pleasantly surprised by how “small town” it felt to be in such a large city.

Reason #2: Our return flight was delayed by a couple hours, which would have us arriving home around 2:00 am. Yeah, not so great with a baby. We chanced it and arrived at the airport early to see if they could switch us onto an earlier flight and the awesome people of Southwest Airlines hooked us up. We were able to fly out around 7:00 pm and Jack and I got home around 11.

Shit Happens {Literally}
I stuck with my plan to change Jack’s diaper right before we boarded the plane. However, within about 15 minutes, Jack decided that it would be a wonderful time to drop a number two. Awesome. Of course, the bathroom with the changing table is located in the very front of the plane (and we were all the way at the back), but it was surprisingly not that terrible to use.

Fast forward a few days…Jack has not pooped the entire trip. UNTIL the plane takes off for our return journey. Yup, within about 5 minutes Jack decides to stink up our entire row and we had to sit there forever until the seatbelt light went off (actually I got up before the light went off and was instructed to sit back down, oopsie). I guess that just goes to show you, you can’t really plan with a kid!

Teething Bites
Remember how I told you that Jack was a laid back baby? Yeah, well not so much when he’s teething. Which he started on Tuesday. I got a frantic “he won’t stop screaming” text from Lindsay about 2 hours before my classes ended. So, we scooped Jack up and ran to Walgreens where we loaded up on Infant Advil, Baby Orajel and Teething Tablets. The poor guy was screaming his head off in pain, but stopped the exact instant I touched his gums with the Orajel. Thank god for medicine!

Between the Orajel and Advil, most of Jack’s pain was kept under control. However, one evening the ache came on really strong and fast and he had a baby freakout while waiting for the medicine to work. Thankfully once the medicine kicked in he went down for an early bedtime and we were able to get takeout to enjoy in our room while watching True Blood.

Week O’ Fun
Even with the conference, the extreme heat and Jack’s teething, we were still able to have lots of fun. We ate some incredibly delicious food (favorites were tapas and an amazing sushi place), saw some sights (loved the Navy Pier at night!), had lots of yummy drinks and did a good bit of shopping too! It was lots of fun, but also super exhausting which is why I totally crashed the entire weekend that I was home.

So, when I say I survived the trip – I truly feel like I deserve some sort of medal for getting through it! Thank goodness I had Lindsay there with me, otherwise there is absolutely no way I would have gotten back home in one piece.

I can’t believe that in only a few days I need to pack up and leave again. But this time it will be just me going to NYC for the BlogHer conference. Just ME! This will be my first time away without my baby and I’m almost indecently excited to sprawl out across the bed in my hotel room and only worry about myself for a couple days!

Here’s some more pictures from our trip:

At some fancy sushi restaurant called Friendly Sushi which had the BEST sushi I’ve had EVER. As you can tell, even Jack wants a piece!
This is how I keep Lindsay happy!

Jack loves his lion souvenir! And you would not believe how many times it took for me to type “souvenir” for spellcheck to figure out what the heck I was trying to say.
The hotel provided us with a crib for a midget. It took Jack about 1.82 minutes to scooch himself to the top of the crib and get his head squished at the end.
And this is where Jack usually ended up.
Bubba Gump…YUM!
Apparently my drink took too long to come and I decided to eat the bucket?

*If you don’t have kids, you’re wondering how on earth a baby pees all over their outfit. I know, I totally thought the same thing. I mean, they ARE in a diaper, right?! Anyways, now that I actually have a little rugrat of my own, I realize that they are magical beings that can somehow pee OUT THE SIDE of a diaper with no warning at all!

**This happened on Friday night. On Sunday morning I went to the Tot Swap and the moment I walked in the door a lady came over to me. The SAME LADY from the shuttle. She said that she really wanted to apologize for shoving in front of me in line to get on the shuttle. She was trying to stay with her group, but that was no excuse for her to get in front of me. She said that she realized that she “acted like a total bitch” and felt guilty all weekend long. I was absolutely flabbergasted, what are the chances that she’d run into me again?!

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3 thoughts on “Visiting Chicago with a Baby”

  1. Hi! I’m about to do the same as you in May! I’m traveling with my 5month old to Chicago. We are going to be staying downtown and I’m contemplating whether or not to rent a car. How did you guys get around besides walking? Did you rent a car or take the subway or taxi? Thanks!

    1. Hi Mai – We didn’t bother with renting a car and just got a taxi when we needed one. Since he was in his bucket carseat it was pretty easy to install it quickly (without the base) in the cab. Good luck!

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