What to see in Chicago in One Day

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I was so excited to explore Chicago for the FIRST TIME a few weeks ago, so I thought I’d whip up a post on What to see in Chicago in 24 Hours, because that’s about the time I had to explore.

What to do in Chicago in one day

I was delighted to be invited as a Yoplait ambassador to attend an event in Chicago, it was my FIRST time going to the city, and it just so happened to be my BIRTHDAY! I debated whether or not I wanted to be away from my family on my b-day, I’m sentimental about that. I actually sent out an email to my newsletter peeps asking their thoughts, and I got 100% response to GO! It also helped that we were going to begin a 20 hour road trip that day, so I’d be packing, not celebrating, so that wouldn’t be uber fun anyway.

With my families support, I decided to go and we had a big celebration the day before and everyone pretended it was my day that day.

{My kids love to run down the street waving when guests leave, and I love that my daughter wanted to do the same for me as I drove away}

With only 8 influencers invited on the trip, I was lucky enough that my local Austin friend Jennifer from Cherish365.com was also going, so we got to be travel buddies! To cut the drama short, we met at the airport for a 6pm Thursday flight to have it delayed, then delayed more, then cancelled! We had a 7am Friday flight (my birthday) so we ended up getting to the event only 30 minutes after it started, so we didn’t even miss anything…yay! But not before we surprised my family at 10pm with a knock on the doorstep saying, “surprise, I’m back!”

Jennifer and I left my house at 5am the next morning, for our 7:30 rescheduled flight. The entire flight was added just for us, we were the lucky ones that actually lived in town. It was a quick 2.5 hours, landing and catching a cab to meet our group for brunch. We arrived at 11am, just 30 minutes after they all came in from their hotel, no biggie!

I wish I could remember the name of the fancy place we ate. They brought out courses of eggs, meats, crackers, and of course displayed on a table nearby was a delicious yogurt bar, complete with the new Yoplait Mix-ins, which are AMAZING! {Cherry chocolate almond, coconut chocolate almond, key lime crunch, mint chocolate delight, salted caramel pretzel}

Yoplait Ambassadors in Chicago

In my hotel room was waiting adorable cookies with my logo on it as well as one with Yoplait on it. They were there for all of us, see below.

I was so delighted to meet up with my friend Mique from Thirty Handmade Days  (below with us waving top left)  She and I have been bloggy friend for YEARS, but have never had much of a chance to chat in person, and I was grateful for that. We got to sit in my room for about an hour and chat about our families.

The main event we flew to Chicago for was to see the “I mom so Hard” comedy show. Funny stuff all about moms. We also got treated to a spa hour, nice massage!

what to see in Chicago in one day

I stayed up late chatting with a few blogging friends, and they all flew home on Saturday morning.

Because my family began our vacation road trip the day before (on my birthday) if I flew back home, they’d be gone, and there was no sense in flying to meet them half way, so I decided to extend my Chicago trip another day. I’d never been there before, and I had some EXPLORING to do!

I was so delighted when my friend Linda was able to meet me there, she lives about 2 hours from the city. She and I met back in 2002, and raised our babies together. I adore here, and it had been a few years since we got together. Last time was when I flew to Illinois to photograph her family 6-7 years ago. We met when we were both poor as dirt. Her husband was in school, and mine was just out of school. We would go out to dinner with friends and split a plate, and make sure that the $10 plate was an ok amount to split. We learned how to be thrifty together.

visiting the bean in chicago

I had a list of the things I wanted to do in Chicago, and this is what it was:

  • Skyline Architecture boat tour
  • Skydeck Chicago Tall Tower (formerly Hancock Tower, formerly Sears Tower)
  • Visit “the bean”
  • Eat deep dish pizza (I had Giordano’s)

We got the Chicago CityPASS  but only got to use it for the Skydeck. It was basically a fast pass through the line in the building which was SO nice! We laughed as we passed everyone in line waiting with the regular passes.It had amazing views of the city, but my friend was a bit scared.

what to do in chicago in one day


what to do in chicago in one day

Linda wasn’t so sure she wanted to go to the glass room that jets out of the side of the building, but with my urging, she was up for it. The crowd laughed and laughed as she clung to me, and when the lady who worked there told us to “look up” she was confused and I grabbed her face. I always know where the cameras are! It was really really funny.

what to do in chicago in one day

I was also really excited about a boat tour around the city. We booked the Shoreline tour, and enjoyed the stories of the city, but we also had lots of chatting to do so only caught intermittent tidbits. Shoreline Sightseeing Architecture tour from Navy Pier

what to do in chicago in one day

I got my “bean” pictures, and we impulsively walked by the theater that showed HAMILTON just to SEE if they obstructed view tickets, and the ticketmaster said, “I don’t have those, but I do have 3rd row seats.” We looked at each other…smiled, and went for it! I just have to laugh, because we’ve come a distance since the day we split a dinner. Because I know everyone wants to know, they were $180 a piece. DEFINITELY more than I do things impulsively. But we are both in a different place than we were before.

It was a highly enjoyable production.

what to do in chicago in one day

I got my deep dish pizza at Giordano’s, and on Sunday we went to an LDS church that just so happened to be at a quaint old elementary school deep in the heart of Chicago.

mormon church in chicago

I’m obsessed with fun and colorful walls when I travel, and I found this wall crawl list of great walls in Chicago, including the one below!

What to do in Chicago in one day

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