So let’s discuss what actually happened last weekend in Chicago. I am now more comfortable in Chicago now than I am in Salt Lake because every part of Salt Lake I was once familiar with has been torn down or torn apart, it’s very unsettling. Chicago has stayed pretty much the same since the first time I went there five years ago and it just keeps getting better the more familiar I become with it.

(Side note: Sunday morning tourists asked me for directions and I was actually able to give them easily, which is pretty much the benchmark of city familiarity.)

So Hotel Allegro in Chicago invited Addie and me to come test out their new kids program with several other moms and their kids over the weekend. (Perhaps you’re familiar with Kimpton hotels? They were super hip before every hotel was trying to be super hip. They own the Monaco in Salt Lake, man have I always wanted to stay at the Monaco.) First glance you wouldn’t see Hotel Allegro and think “FANTASTIC PLACE FOR KIDS!” because it’s very hip, and very cool. Potty training ruined my hip and cool and I’ve been very self conscious ever since. Addie was greeted with a Kimpton Kids bag full of fun stuff to keep her busy, the staff was always excited to see her running around and they even had a child sized leopard print robe for Addie to wear which clinched her Hotel Allegro loyalty.


Since we didn’t have Vivi with us Addie INSISTED on using the stairs for everything. In fact at one point she insisted that we ride the elevator up to the top (19th) floor, then take the stairs all the way down. I began getting queasy with all the around and around on the 11th floor and had to finish out the descent in an elevator. We ended up compromising with riding the elevator to the 3rd floor then taking what we dubbed “the fancy stairs” to the ground floor. (There were exactly 69 steps to the ground floor, I decided I’d count on my fifteenth trip down them.)


The hotel set us up with passes to some of the most popular area attractions, public transit credits, a map and a challenge. If we completed a five stop scavenger hunt by the time we checked out Addie would get a prize. A PRIZE. I laid out the map and began plotting the best, most time efficient route to check off all five stops and still have time for other activities. Addie just wanted to run up and down the stairs but I insisted on mapping out our route so as to win and not waste a single moment.

This is where I segue for a moment and say I am a MASTER of public transit. I live for public transit and Chicago has some really good public transit among buses, subways and trains. Even without public transit I am really good at planning out super efficient routes with minimal time wasted and all opportunities taken. This special skill of mine is what leaves me INFURIATED on on the third to last episode of America’s Next Top model every season when the girls are given 4 hours to do 5 go sees. PLAN IT OUT BEFORE YOU SET OUT GIRLS, YOU’LL GET BACK WITH PLENTY OF TIME WHICH IS HALF THE BATTLE.

Friday night Addie and I met all the other moms and hotel staff in the lobby for Kid’s Hour which included tasty lemonade, popcorn and a rousing game of Chicago themed Connect 4. Addie and I took a trip down Michigan Ave. to the Lego Store, American Girl Place (Side note: Addie could care less about  American Girl Place but insists on going there every time we’re in Chicago) LUSH, and the Disney Store where she picked up a sweet bow and arrow as her souvenir. Since we still had daylight to burn we walked over to the Sears Tower (I know it’s been renamed the Willis Tower but that name is stupid, it will always be the Sears Tower) and took a one minute 103 floor elevator ride to the top, Addie then shouted “I DIDN’T KNOW CHICAGO WAS BY THE OCEAN!” before we stood in a giant glass box and looked down 103 floors down.


We then took the 103 floor one minute elevator ride down, ordered a stuffed cheese pizza from Giordano’s, went back to our hotel room where cookies and milk were awaiting our return. We gorged ourselves as we watched The Lorax in our matching animal print robes before Addie asked (ASKED!) if we could go to bed at 10:15 pm.

Day one and items #1 (Sears Tower) and #2 (Chicago Style Pizza) on the scavenger hunt list? Check, check and check.

As soon as the sun was up Addie was up shooting arrows at any solid surface in our room, which at one point included my head (accidentally.)

Since we didn’t have to be to lunch until later I let Addie order from the room service menu. Y’all? THE KID’S MIND WAS BLOWN BY ROOM SERVICE.

How to impress a seven year old, leopard robe and room service.

We could have ended the trip right there and she would have come back to Indiana a changed woman. But the day was only getting started. By the time we were ready to leave for lunch with the whole group Addie put on her sensible shoes only to realize her feet had apparently grown one size in a month.


Tiffany Glass ceilings make buying $30 running shoes way more posh.

With shoes that fit we headed to lunch with everyone at Millennium Park before breaking off to complete our scavenger hunts. Addie and I took a detour to The Bean (Cloud Gate) then checked off item #3 in front of Crown Fountain. Addie didn’t want to get wet for some crazy reason, I’m convinced the Tiffany Glass Ceiling shoe buying experience made her older and somewhat less fun.



We then boarded the train to Lincoln Park Zoo (scavenger hunt item #4) where Addie had her first experience with Dippin’ Dots (two thumbs up!) and a Gorilla. (“MOM! I can see his butt!” *giggle giggle*) Just as soon as we got to the zoo we were off again on a bus/subway down to the Field Museum. Addie wasn’t really okay with the subway. “TOO DARK!” she declared. Once we made it to the Field Museum Addie took over.

“HALL OF GEMS! BIRDS! DINOSAURS! MUMMIES! WHAAALLLEEESSS!!!!” Her favorite was the mummies but she won’t admit it, she asked to go back to the exhibit three times. As we were getting ready to leave we caught sight of a Mold-A-Rama, something I can remember vividly from my numerous childhood trips to Hogle Zoo in Utah but was never actually allowed to do.


It was so worth $2 to stick it to my mom and make that cheesy dinosaur souvenir from what is most likely toxic plastic.

I wasn’t alone in my Mold-A-Rama desires either, dozens of people on twitter said they were never allowed to make one either and that they now must go to Chicago to procure one.

Final stop on our scavenger hunt? Check. Childhood nostalgia vicariously experienced through my oldest? Check.

It was back to the restaurant at the hotel, 312 Chicago for dinner and y’all? Meatballs are delicious. Addie ate about 12. She set a trend for kids at the table ordering Shirley Temples and as if the fancy drink and meatballs weren’t enough a giant hunk of a chef came in with a deliciously enticing Italian accent and asked if the kids would please follow him to the kitchen so they could make pizza with him. I’m not stupid, I followed right along because that man with the accent (Chef Luca) was going to be helping my kid cook, meaning he was going to be talking a lot with his accent and I wasn’t going to miss out on that.

Cooking with Chef Luca. (I liked Chef Luca *ehem*)

I took pictures of course, it would have been weird to just stand there listening to Chef Luca, which is reason #342 why I love being a photographer, you have an excuse to stand near very attractive chefs with very scintillating accents as they help your child make pizza.

Cooking with Chef Luca. (I liked Chef Luca *ehem*)

Cooking with Chef Luca. (I liked Chef Luca *ehem*)

(The pizza was delicious.)

I spent part of the evening talking with Mary, the hotel’s general manager (who brought her own seven year old son along on all of our adventures) and told her how happy I was to have Addie see moms and women as managers. (Turns out the CEO of Kimpton is a woman as well. WHEE!) After dinner we went back up to our room and watched Mirror, Mirror which is easily one of my new favorite movies. Addie had some harebrained idea that we were going to go watch fireworks on Navy Pier at 10 pm but she was out cold by 10:01 pm.

Day two? Check.

SUNDAY! “CAN WE HAVE BREAKFAST IN BED AGAIN? I WANT THE SAME THING BUT THIS TIME WITH MORE WHIPPED CREAM!” as then she proceeded to jump back and forth between the beds before I had even put my contacts in.


Breakfast was served but french toast, strawberries, and hot chocolate didn’t seem like enough so we headed out to procure cupcakes as a second breakfast.


We met up with everyone else and rode a trolley to Ed Debevic’s where we were verbally assaulted and served cheeseburgers and fries. If I could work somewhere for a day? It would be as a server at Ed Debevic’s.





The trolley then took us down to Navy Pier (I love open air tours, our driver was amazingly knowledgeable and kept up with ALL. THE. QUESTIONS. from the gaggle of seven year old children on board.) where we boarded a SeaDog Cruise and basically had our faces blown off by fresh Lake Michigan air as we learned more about Chicago and saw the city from a whole other angle.

We didn’t have to board our bus back to Indy for a few hours so we wandered around the streets of Chicago some more before checking out of our lovely hotel room and bidding the marvelous staff of the Hotel Allegro adieu.  (The bellhops kept a close eye on Addie and her comings and goings, paying attention to little things that made her feel very, very important.)

The temptation is always there to book the cheapest hotel possible because you’re really only there to sleep, right? Wrong. I’ve learned that when it comes to booking a hotel (ESPECIALLY with kids) you have to book one that has special accommodations for kids so they don’t feel left out and one that you enjoy being at when the day is over (or when you just need a rest and escape from all of the busy) otherwise you’ll just leave your vacation feeling as though you need a vacation. Having a hotel in the middle of everything meant we were never far from something to do (or new shoes at 10 am.)

I will always be forever grateful to Hotel Allegro for inviting us up for the weekend at a time when both Addie and I desperately needed to get away with each other. Thank you guys for taking such good care of us and for inspiring me to take annual trips just like this one with Addie from now on. If there’s a Kimpton where we’re going? We’ll be staying there. Chicago? We love you, until next time. -Addie and Casey


Huge thank you to Hotel Allegro for putting us up for two nights, giving us passes to so many attractions and for feeding us throughout our stay. All opinions are our own and we were not compensated or influenced in any way (I mean, aside from awesome, we were influenced by awesome.) To find out more about Hotel Allegro “Kids Rule” Summer program or any other Kimpton properties, visit


(Anything to add Addie? “Can we go back tomorrow?” “No.” “Darn.“)



  1. Awesome trip! (There will never, ever be a picture of my feet like the picture of your feet on the glass floor … NEVER in a million years!)

    You make me miss Chicago, which we left 16 years ago to raise kids in more laid-back Iowa. Also – did you know that the first Ferris wheel was built in Chicago in 1893? Fact. And I think there are Mold-a-ramas at the Museum of Science and Industry, which has loads of cool stuff you should totally take Addie to next time (baby chicks hatching!).

    Casey Reply:

    @CaySedai, We did the Science and Industry museum the first time we went! And yes! The first Ferris wheel cars held 60 people and had BARS IN THEM! World’s Fair WHEE!

  2. I want to take my girl to Chicago and have an adventure.

    Casey Reply:

    @Nichole, Stop by Indy on your way there!

  3. Oh man, it sounds amazing! What an awesome thing to get to do with Addie. Also, hotel bed jumping is the best.

    Casey Reply:

    @Rachael, I did not partake, for Addie it’s fun, for me it’s a liability.

    Rachael Reply:

    @Casey, Yes, I guess what I should have said is that it’s the best for people under 18 or 19. After that it’s just painful. And potentially destructive to property. 🙂

  4. mommabird2345 says:

    Sounds like you had a wonderful trip! Glad you both had a blast.

    So, what was the prize for doing all 5 things??

    Karen T. Reply:

    @mommabird2345, that’s what I’m wondering too 🙂 Sounds like you had an amazing time. Can’t wait to do this with my daughter (1.5 right now!) someday!

    Casey Reply:

    @Karen T., A sweet kids book about Chicago and a picture frame (which has yet to hold a picture.)

    Casey Reply:

    @mommabird2345, Oh! A cool kids book about Chicago and a sweet picture frame!

    Mommabird2345 Reply:

    @Casey, Nice!

  5. Whew – you two did it all! Sounds like it was an amazing trip! My favorite is the Mold-O-Rama. I think I had a red gorilla from the Como Zoo in MN. Great post!

    Casey Reply:

    @Alisa, We did do SO MUCH. Makes me so happy you remember your Mold-A-Rama!

    Alisa Reply:

    And it will always be the Sears Tower, the Willis Tower is just dumb! Don’t forget to watch all the gymnastics with Addie this weekend! I can’t wait for the Olympics.

  6. This post makes me SO glad I’m going to Chicago at least 3 times in the next 2 months.

    I wish I had your gift for public transportation though… I always end up paying an arm and a leg for cabs because I am travel-dumb.

    Casey Reply:

    @ClassyFabSarah, I shall teach you the ways of public transit young one.

  7. You look like you both had the time of your life- I am so happy! I love Chicago, and you!!!


    Casey Reply:

    @Stephanie Precourt, I love that you’re the one that introduced me to Armitage! Can’t go there without thinking of you!

  8. What a great trip! I can’t wait to do those things with my baby girl. Well, except for standing in that glass box. The picture alone made my palms sweat.

    Casey Reply:

    @KDA, It wasn’t that bad once you’re in it! The glass elevator in the CN tower was way worse.

  9. I heart Chi-town. And thanks for calling it Sears Tower. Too many iconic buildings and sport arenas are changing names these days. Nothing is constant anymore…I’m kind of a traditionalist. It’s been a year and a half since I’ve been in SLC, so I’m preparing for a surprise when I visit family this August.

    Casey Reply:

    @Britta, I hated seeing all of the iconic signs with giant sponsor logos on them. Chase Chicago theater, Ford Oriental theater, Cadillac Palace theater. Sheesh.
    And yes, downtown is insane now. Prepare yourself.

  10. I love your sandals in the picture at the Sears, I mean Willis Tower! Who makes them?

    Casey Reply:

    @Erin, Merrel! I got them four years ago and they are SO. COMFORTABLE.

  11. I lovely lovely love this post! So glad you two got a special weekend together! And I’m sold–if (when?) we go to Chicago, that’s where we’re staying. Dean thinks hotels are the greatest anyway—this place will blow his mind!

  12. This looks like the best mother-daughter weekend EVER. How cool! Surely a trip you’ll both remember forever.

    And I love that Lake Michigan was Addie’s little ocean 🙂

  13. I totally agree, sears tower forever. We’re in Chicago for the next 10 days (can’t believe I missed you) and I plan to take my kids to most of those places!

  14. Melissa says:

    Chicago is wonderful especially in the summer – we live about 30 minutes away in NW Indiana. We love coming down your way though too – Indy is our favorite. 🙂 Our girls love it too!

  15. Your post and the photos made me miss my hometown so, so much! Glad you both had a good time.


  1. […] never allowed to do as a kid or things I wasn’t able to do in our early years of marriage. The Mold-A-Rama is a perfect example of “Wait, I’M THE GROWNUP, I can totally do that if I want to.” I feel the same […]