Phoenix’s First Visit to Chicago

Michigan Avenue

Since moving to Nashville, when visiting our families, Jordan and I attempt to fit in a day to explore Chicago. It doesn’t always happen, but my parents live too close to not try!

We lucked out with amazing weather (for Chicago in November). Chilly, but sunny! You can’t ask for anything better. Chicago had their first snowfall the following week. While I actually enjoy snow at this time of the year, I didn’t really want to have to navigate it with Phoenix. The snowsuit I thought Phoenix could fit in this winter is too big on him right now. He’s such a little peanut!


Most of Jordan’s family was able to join us. We hit up our usual spots while keeping close to Michigan Avenue. The Magnificent Mile is so festive during this time of the year. Phoenix enjoyed people watching, when he wasn’t napping in his stroller. Bless those stroller naps.

I get asked often for suggestions on things to do and places to eat while in Chicago. I have several answers, all depending, on the season and how far you want to stray from where you are staying. Chicago is a large city! We have favorite spots that aren’t downtown, but usually (when we only have a few hours and want to meander) we stick along Michigan Avenue.

I bought a dress at Zara for our holiday cards. I’m so excited to share those with you. For lunch, we ate pizza at Lou Malnati’s. Seriously, do yourself a favor, next time you visit Chicago eat deep dish pizza somewhere besides Giordanos. There are far better options! We grabbed shakes to go at Shake Shack. I LOVE that Chicago has two locations now!



^ Phoenix has been Mr. Drool Monster as of late. He wants to chew on something constantly, but I’m not sure if he is really teething or if it’s just developmentally normal for this age.

Michigan Avenue


^ You know what’s pathetic? I’ve never been to the top of the Sears/Willis Tower. I only lived in Illinois for 20 years!!





If you are ever visiting Chicago and need any suggestions, don’t hesitate to reach out!

18 thoughts on “Phoenix’s First Visit to Chicago”

  1. I think I would pass on going up in the tower anyway. I’m not good with heights!
    I’ll definitely come to you for suggestions if/when we ever plan a trip to Chicago. I’ve heard a lot about Giordanos but it’s the same as in NYC…there are places everyone will tell you to go to, because that’s where they were told to go and the only place they tried, but there are probably better options.
    I can’t wait to see your Christmas card photos.

  2. Phoenix is such a cutie!! We went to Chicago on our honeymoon, and had a really wonderful time. We rented a tandem bike and bicycled along the riverfront. We ate pizza (but of course), and went to both Chinatown (food was SO GOOD) and Littly Italy. We drove around exploring. We ended up finding so many little adventures on our own while we were there including stumbling across the Chicago Symphony Orchestra’s outdoor concert, and then returning later to get to see Thomas Hampson (one of my hubby’s favorite singers) in concert. We even got to meet him afterwards! There sure was a lot going on in mid-July while we were there. We originally dreamed about going to Italy for our honeymoon, but as exhausted as we were after pulling off our DIY wedding, I am honestly glad we went somewhere a little more low-key where we didn’t feel like we had to see all the things in order to make our airfare worth it. I bet it is exceptionally beautiful this time of year. What a fun outing for your sweet family.

  3. Chicago is definitely on our US travel bucket list! We’ve been meaning to go, but the timing is not always right. Hopefully next year we get to go! I might reach out to ask for recommendations when I start planning our trip! 🙂

  4. How adorable! What I wouldn’t give to transplant myself there simply for the weather – it’s so muggy and hot here in TX. Wishing you all the very best for the holidays!

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