Our Chicago Vacation

First of all, is it really a vacation with two kids in tow??  Turns out, going to dinner every night is not quite as enjoyable as it used to be...not to mention, crazy expensive in a place like Chicago!!   And I once read an article comparing a vacation and a trip.  Needless to say, if there are kids along, it's no vacation!!

Anyway, as much as we wanted to go back to Florida this summer, with the country up in arms about Zika, we decided that heading south would not be in our best interest, so we went north instead.  We chose Chicago partially because it's a kid-friendly city, but also because we wanted to hit up a Royals/White Sox game.  Turns out, the only time the Royals would be playing in Chicago all summer long was the weekend six weeks post-knee surgery for Craig, and because it is such a walking city, we decided to forego the Royals game and gave his knee four extra weeks to recover.

So last Thursday evening, we took off for my parents' house in Iowa - about four hours from Kansas City and halfway to Chicago - and finished the drive on Friday.  Of course, upon checking into our hotel, the boys immediately wanted to jump on the bed, which gave me the perfect opportunity to make my first-ever Boomerang video. :)

We stayed at the Hilton DoubleTree Chicago - Magnificent Mile.  It was about three blocks from Michigan Avenue and five blocks from Navy Pier, so the location couldn't have been much better!  There was an Einstein Brothers in our hotel and a grocery store next door, which made for convenient breakfast/bottled water/beer runs.  I booked the hotel on Priceline and got a pretty decent deal, but we still had to pay a ridiculous amount of money for parking.  Such is the Chicago life, I guess!

For the most part, we tried to do one major activity each morning, then back to the hotel for naps, and one more activity after naptime.  Attractions got so busy around lunchtime though, everything was much more enjoyable in the 9/10-o'clock hours in the morning!  Although we took an Uber twice while there, we packed two umbrella strollers (had to buy a second one!) and walked nearly everywhere!  Luckily, we had amazing weather while there--an average around 80 and partly sunny most of time time.  Our final day was the only hot and humid day, and boy am I glad, because I could barely handle all the walking in that weather!

Unfortunately, the boys both came down with hand, foot, and mouth disease while there.  Brantley started acting weird on our first full day in Chicago (Saturday).  He wouldn't eat, wouldn't talk, and was just plain cranky.  We chalked it up to a major lack of sleep (4th of July was just five days prior) and him being completely overwhelmed by all the people.  He was a total downer and it was putting the entire family in a bad mood.  He seemed okay the next morning (after a stern chat from Daddy) and we had a super fun day...also our 6th wedding anniversary.  We had an Italian dinner that night and midway through dinner, as quickly as the flip of a switch, Holden started acting weird, as well.  He was fussing uncontrollable and kept saying his nose hurt.  Like any parent, we assumed he got pasta stuck in his nose. :)  It was shortly after that that I felt his forehead and knew instantly he had a fever.  Craig went to pick up some saline nasal spray (you know, for the pasta) and Ibuprofen from the nearest Walgreen's, while I held Holden on the bathroom floor in our hotel room, just certain he was going to throw up.

On Monday morning, his fever was still present and he was in no shape or form to go sightseeing.  Although completely back to normal personality-wise, Brantley woke up with sores around his mouth...and so began my suspicions of HFM.  (I noticed sores on his arms, legs, hands, and feet later that day.)  Because he acted fine, I suggested Craig take Brantley to do something fun and I offered to stay in with Holden.  Holden is a total mama's boy period, but even more so when sick.  We snuggled, he slept, and I caught up on blog reading.  I also counted down the hours until his next dose of Ibuprofen could be administered because it was obvious he was miserable!  (I did get to sneak out during naptime for a little shopping along Michigan Avenue...so don't feel too sorry for me!  It was also during this time that I called our pediatrician's office back here in KC.  They confirmed the HFM as much as they can via phone and said, unfortunately, there's nothing you can do for it.)  There was an AMC theater just a few blocks away, so Craig took Brantley to see The Secret Life of Pets that evening, while I stayed back and watched The Bachelorette. :)

On Tuesday morning, Holden woke up with a similar rash as Brantley's, but his fever seemed to have subsided, so we resumed our normal family-of-four activities (hallelujah!).  However, it was obvious Holden was in quite a bit of pain so around 1pm, we decided to go back to our hotel, pack our bags, and head home about 17 hours earlier than planned.  Honestly, it was so hot that day that we had no interest in doing anything else outdoors, plus we knew Holden would be miserable if we tried to do something touristy.  We were more excited about the thought of driving home in hopes of the boys sleeping a good portion of the way than we were about staying one more night with a miserable kid.  We pulled out of our hotel's parking garage around 3pm, which meant we hit some pretty bad rush hour traffic and what should have been just under an 8-hour drive was more like a 9 1/2 hour trip.  We got home at 12:30am (Wednesday morning) and the boys (Brantley's rash, Holden's attitude) have been slowly improving ever since.

Now for the rest of our trip - the fun we had before the crazy illness and of course, the pictures!  I have broken them down by day.

Day 1 // Millennium Park, The Bean, and Giordano's

After checking into our hotel, we took off walking towards Millennium Park.  The park is home to The Bean, which is what I really wanted to see (i.e. take photos by!).

We asked a random lady to take our picture by The Bean.  I guess I should have zoomed out my camera lens first...because clearly she didn't do it!  Anyway, I promise we were, in fact, at The Bean, even though you can't actually tell!

We walked across the street for dinner at Giordano's, famous for Chicago's deep-dish style pizza.  The nice thing about this place is that you can place your order while waiting for a table so once you're seated, the pizza is ready.  We got our table pretty quickly so we still had to wait awhile for our pizza, but it's a good idea in theory!  Brantley was obsessed with this fountain outside of the restaurant and could have run around it for two more hours!

Craig wasn't (and isn't) a huge fan of Chicago deep-dish ("I like Pizza Hut better") but I could eat it every other night!  Holden agreed.

I tried to snap a few photos of the boys on the walk back to our hotel, but they were anti-cooperative.  Sigh.

Day 2 // Architecture River Tour and Willis (Sear's) Tower

Both mine and Craig's favorite part of the trip was the architecture river tour.  He was excited from the get-go (he's a history buff) and I was just excited for the boat ride, but I actually enjoyed a lot of the history, as well!  Well...as much as I caught anyway; Holden got a little antsy during the 90-minute ride so I had to do my best to keep him entertained.  (This was also the day Brantley started acting weird.  You can definitely tell in a lot of these photos.)

After naps that day, we took an Uber to the Willis (formerly known as the Sears) Tower.  The Willis Tower was once the tallest building in the world (now the eighth) and is the second tallest building in the U.S. behind the newly constructed Freedom Tower in NYC.  We bought our tickets ahead of time, which saved about 30 minutes, but we still waited in line for about an hour and a half before finally reaching the top.  The Willis Tower is one of those things you have to do once in your life, but it's a bit underwhelming and overpriced just to go to the top of a really tall building. 

The biggest attraction at Willis Tower is The Ledge, a glass overhang 103 stories above the streets of Chicago.  We waited another 25 minutes for our turn on The Ledge and despite the pep talk I gave myself the entire wait, I just couldn't do it!  I could barely even muster up the guts to snap the boys' photo on it!  All I wanted to do was pull them off and hold them safely in my arms!  So I didn't get the best photo, but I was happy to have them back on the normal floor.  For the record, Craig couldn't do it either!  (And for the double record, I woke up multiple times overnight that night with visions of that glass floor falling through!!!!!!)

Also worth the mention, for lunch this day we went to Portillos and had Chicago-style hot dogs!  I could have eaten one of those every day!


Day 3 // Navy Pier, quadcycle ride along Lake Michigan, roof top swimming, and our 6th anniversary dinner 

Day 3 happened to be July 10, also known as Craig and my sixth wedding anniversary!  We started the day by walking a few blocks to Navy Pier and taking a ride on the famous Centennial {Ferris} Wheel.

After the ferris wheel, we decided to rent a quadcycle and ride it along Lake Michigan for an hour.  Brantley and Holden both loved it and we must have been quite the sight because everyone we met  smiled/laughed at us! 

Despite how it looks, it was actually hard work pedaling this thing!  I decided I would have enjoyed it more if it was motorized. ;)  However, don't be fooled.  Craig did 90% of the work while I took videos and selfies. ;)

Back at our hotel, we decided to take advantage of the rooftop pool.  I mean, it's not often you can swim on a roof surrounded by skyscrapers galore!  It was a bit chilly though, not gonna lie!

 For dinner that evening, we walked to a local Italian restaurant and had dinner on their patio.  It was unlike any anniversary dinner we've had to date, you know, because of kids and all!  And this was the dinner Holden snapped his fingers and decided he didn't feel well......or he may have gotten pasta in his noes, we'll never know! ;)

I snapped this photo below with my iPhone on our way back to our hotel.  It ended up being one of my favorite photos from the entire trip!

Day 4 // The beach and Michigan Avenue shopping (for me)

I don't have a ton of photos from this day because this was the day I stayed with a sick Holden in the hotel room.  Craig took Brantley to the beach and apparently, he loved it.  Like he was running, diving into the sand, and acting like a crazy kid according to Craig.  (His HFM sores didn't bother him one bit!)  I really wish I could have seen it, but it was probably good for Craig and Brantley to have a little one-on-one time.  They stayed at the beach for far longer than I expected they would.  Every time Craig suggested leaving, Brantley flat out refused.

When I finally got out to do a little shopping, I took a photo of the bump along Michigan Avenue!

That evening, while Craig and Brantley were at the movie, I decided to grab some dinner.  I called in my order to PF Changs, which was only a half mile away on the other side of Michigan Avenue.  As I was walking to get my order (with Holden in the stroller), three police cars pulled up to the curb with their lights on, quickly got out, and headed in the same direction as me--towards Michigan Avenue.  When I arrived to Michigan Avenue (one block further), I noticed quite a few police lining the corner of the intersection and more police cars pulling in by the second.  My heart started beating out of my chest and I quickly realized a Black Lives Matter protest was coming around the corner.  I wasn't sure what to do, as security guards were standard guard their businesses and employees were locking all doors along Michigan Avenue!  I quickly ducked into a business (which I thought was a hotel, turned out to be a shopping mall type place) as two girls came out and watched with wide eyes as {what seemed like} hundreds of police lined the block.  I still didn't want anything to do with the protest or be anywhere near it so I took off in the shopping center until I found an information desk and someone to direct me to {the safest way} to PF Changs!  Being alone with Holden, this was such a scary situation and for once, 15 minutes later, I was thrilled to be safely back in our hotel room with a sick kid!

Day 5 // Water taxi to Shedd Aquarium

When Holden woke up fever- free the next day (Tuesday), we decided to make the most of our last full day and head to Shedd Aquarium.  We walked to Navy Pier and took a water taxi to Shedd.

I thought Shedd Aquarium was a complete waste of time and money.  I'm so sorry if this is your thing (no offense at all), but it's just not mine.  I guess I thought it would be cooler than it was--bigger fish, bigger aquariums, more interactive maybe?  But it wasn't and I will never go back.  It didn't help that we had one cranky kid who wouldn't even put shoes on thanks to his HFM sores.

Brantley tried to touch a sting ray, but they never came close enough.

We stopped for one final photo opp and then headed back to our hotel to pack.

The car ride home was pretty miserable at times with a crying, whiny toddler who was in obvious pain, but we made it safely which I am very thankful for.

Despite the setback, it really was a great vacation trip!  Lots of fun was had and lots of memories were made.  And it's crazy to think that our next vacation will be one with our family of five!!


  1. I'm so sorry the boys got sick while you were on your trip. I feel like that's a normal occurrence. Ha ha. Ours were sick as we left on our beach vacation, so I've decided that kids just know we are off to have to fun and get sick to spite us. ;) J/k. Minus the sickness you guys packed in a lot and wow does it look like fun. I love Chicago so much! It's one of my favorite cities. Did you buy anything fun while out shopping?

  2. Sorry they got sick, that stinks! This looks like such a great trip, the joy in their faces is so cute! I have never been to Chicago, I hope to soon and I will remember all the fun things from this post when I plan my trip! have a great weekend!

  3. I'm sorry your kids got sick and I'm glad you had some fun anyway. We need to get to Chicago! It's been years!

  4. So glad I saw your post after a long hiatus from blogging. Congrats on the bump!! Yay for Chicago, boo for Hand, Foot and Mouth. It's such a long and drawn out virus plus it sucks for the kids. Glad you liked Chicago! Looks like you had a blast.

    I totally agree that the Aquarium is a waste of time and money. MSI has always been a better option for our family. Still expensive but much more fun for everyone.

    Random question: is your stroller two singles made into a double?

  5. Chicago will always have a special place in my heart - Tim and I got engaged there 5 years ago (my very first blog post is actually all about that trip!). You got so many great photos - love them all! I’m sorry that you guys were plagued with HFM during your trip though, such a bummer!

  6. What an AMAZING trip aside from the boys getting sick! I feel like that happens to us every single time we try to go on vacation. Such is life with littles, I suppose! I've never been to Chicago before and I am DYING to go. Hopefully we can get up there sometime in the near future!

  7. I was in Chicago the same weekend as you! My mom and I went to the Navy Pier, Giodano's, Portillo's, the Bean, AND when we were shopping on Michigan Ave, we came across the same police activity! You and I were probably there at the same time!

  8. Looks like you had a blast! I'm from Illinois + can't wait to visit Chicago next month :) You can never go wrong with a stop by the Bean and a trip to Portillo's!

  9. I think you guys should do a redo. So sorry the boys got sick, but it looks like you made the most of it! Luke & I have been to Chicago a few times when we were dating, but haven't been back since. We definitely need to make a point to go back. Did you get anything fun while shopping??

  10. Poor buddies with the hand foot and mouth! We've never had that *yet*, but it sounds like no fun! You totally rocked this trip, though! What fun adventures!!

  11. Hate that the boys got sick!! But, kinda glad to know Stella isn't the only kid who is completely stuck to mama, and she is terrible when we eat out. It's exhausting traveling with kids and I'm so impressed you did it while pregnant...way to go!

  12. You did so much! Glad you had a good time despite the boys getting sick.

  13. I adore Chicago! You did all the best things. And I totally agree, skip the aquarium.
    I'm so sorry the boys both came down with HFM. :( But, it looks like you were able to have so much fun while you were there!

  14. I think you've done more than me and I live 20 minutes from the city, LOL!! How fun though, despite the HFM the boys got!

    I agree, the Shedd is just whatever, but the Planetarium is awesome!! I could eat Portillos every single day too! We have the Navy Pier Ferris Wheel on our summer bucket list, I hope I don't chicken out though!

  15. Sometimes you need a vacation from your vacation when kids are involved! Ha! It’s tough, but it’s worth it and the memories that are made. Zika is so scary and I don’t blame you for not wanting to chance it. I will say though, I am a mosquito magnet and I didn’t get one bite while in Florida. However, here at home in Texas I can step outside for 1 minute and have no less than 5 bites. It’s frustrating! Boomerang is such a fun app, but I keep forgetting that I have it. Oops! I hate that they both got HFM. That is the worst!! Looks like a great trip (minus the illness). I’ve never been to Chicago, but hope to one day. I definitely would not be able to do the Ledge, either. I’m having a bit of anxiety just looking at these pictures. Brave boys! Hope y’all had a great anniversary! Adorable photos! I love how many family photos you got. That’s something we failed at on our trip.

  16. I am headed to the Windy City in just a few days and can't wait. First thing I want to do is bash some Chicago pizza!

  17. I am beyond bummed that Shedd Aquarium was a bust! We love our Aquarium but know we are totally spoiled! My gramma grew up in Chicago I would love to visit the Windy City with her. I will say that Im not a heights fan so all this sky scraper stuff had my heart going lol. I adore the cross walk picture too!

  18. I'm orginally form the Chicago area so I loved reading this post! So many things have changed since we moved! I haven't been to the Sears Tower since they put those look out things (kind of scary) and the gondola at Navy Pier is a new one! Sucks that the boys got sick. Myles had that once before. He got it when we were traveling as well and I just figured it as tried and cranky from time change and travel too! Then I noticed the sores and it all came together. Glad oyu still got to enjoy some of your trip though!