A Winter Weekend in Chicago

Good morning from Chicago! What a beautiful city. I’ve only ever been here once before, and it was 20 years ago, so I don’t remember much about it except that it was freeeeezing cold… in June!

Well, Chicago redeemed itself this weekend, as they are having unusually mild weather for December. It’s been absolutely beautiful. I’ve been documenting our trip on my IG story, in case you want to follow along!

Paul travels here often for business, so he was excited to show me around. After we got settled into our hotel on Friday afternoon, we went out to explore. We walked by The Christkindlmarket, which was mobbed, so we bypassed that and walked over to Michigan Ave., where we wandered a bit before our dinner reservations at The Bazaar by José Andrés.

That was pretty much one of the best meals I’ve ever had in my life, but even better than the food was watching the bartenders create their masterful cocktails. (Paul reserved seats at the bar, rather than a table, so that was fun.)

When we got back to our hotel, there was a jazz band playing in the bar there, and it wasn’t terribly crowded, so we plopped down in a pair of comfy club chairs and enjoyed them for a while. They were quite entertaining. They told us it was their first time playing together, and they were basically putting their music together on the spot. So that was a fun way to end the evening!

After doing some work in the hotel lobby yesterday morning, Paul and I cabbed it over to Michigan Ave. to meet my friend Shelly for coffee. She just so happened to be in the city for the weekend, as well! Her Walkabout trips always look amazing; one of these days, I swear, I’m going to make one of them!

It was the perfect day for exploring on foot, so from there, we meandered over to the Riverwalk and then over to Millennium Park.

After that, we made our way back down Michigan Avenue, and stopped in a few stores before cabbing it back to our hotel for lunch and a nap.

The point of our trip was to attend Paul’s company holiday party, and anyone who has been following along knows that I tried approximately 20 dresses before deciding to wear this one.

I never did bother to shop for different shoes. I decided I didn’t care enough to spend my time in Chicago shopping, and these worked out just fine. Here are a few more photos from the evening.

We asked someone in our hotel to take a picture, in case it was awkward to ask anyone at the party. I wanted to be sure we got something, but she cut off Paul’s head and our feet in every single one, lol. I’m still sharing because the lighting was perfect.

The event was held in a private room at The Dalcy, which was a really cool venue. The restaurant looked nice too; I’d love to go back sometime and eat there.

I snapped this in the mirror in the lobby. As you can see, I decided to wear a faux fur jacket.

full outfit details

And then, as we were leaving, we did get this picture, so you can sort of see the event venue in the background too.

I’m sure you are all wondering if I was happy with the outfit I landed on, and I was. It was perfectly appropriate for the event, and I felt like it represented my personal style in the best way possible.

We had a lot of fun, meeting some of Paul’s co-workers and their spouses. I’m really glad we came out for the weekend, and that we decided to take an extra day for sightseeing. I definitely hope to come back to Chicago before another 20 years go by!

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37 Responses

  1. Loved reading this. You looked beautiful and I hope you wear the dress again sometime at another event. Paul looks nice too. Great pictures of you both. I’m glad you had great weather to sightsee. I have a friend who lives in Plainfield, Illinois, so close to Chicago. They get a lot of Winter snow, but so far not much this year. Have a great Sunday afternoon.

  2. You look beautiful! The dress was a very good pick. Paul’s suit looks good too! Hope you both had a fun time and a safe trip home.

  3. You and Paul look very nice! It sounds like the weekend getaway was enjoyable for both of you. Enjoy the rest of this second Sunday of Advent.

  4. You both looked amazing! I only live a few hours from Chicago, but I haven’t been sightseeing there in forever. I will have to change that!

  5. Wasn’t this a Black Tie Optional event? And, if so, am curious about Paul’s decision to not wear a tie at all. Wouldn’t that be dressing for a more casual event?

    1. Yes, please educate us on the tie situation! I see another man in the background without a tie. So how do the black tie optional rules work? Thanks! You both look stunning! Good dress choice!

  6. Thank you for sharing – I was wondering how it all went!! You were absolutely beautiful. 🙂 I’m curious what (if any) fashion trends you spotted in Chicago? Anything you hadn’t seen at home?

    1. I did try to pay attention, although we were probably seeing a lot of tourists. I did notice that no one was wearing full length flares or bootcut jeans. Most were straight ankle, and I saw a couple wearing the wide leg and crop flares in a way that looked stylish. I noticed a lot of teddy coats and long wool coats. Puffer coats weren’t as plentiful, but the ones I saw were serious winter coats – The North Face, Patagonia, or Cananda Goose.

  7. The dress and accessories look great together! Looks like it was a good fit for the event, and I’m glad you felt comfortable in it. Looks like a fun trip, hope y’all have had a great time!

  8. What a lovely couple you are! Beautiful! When we went to Chicago it was 8. That’s an age and should never be a temperature!!!!! We took the river architectural tour and it snowed. It was April!!!!! Glad your dress worked —you look fabulous in it. I see you in it for New Year’s Eve with champagne and funsnacks !!!!!

  9. You looked so beautiful! Loved your choice and the accessories were just perfect. Glad you chose the black fur wrap. Daytime outfits were stunning as well.

  10. You look absolutely stunning! And I love what you wore to walk around town. You and Paul are a gorgeous couple-so glad you had a great time.

  11. Perfect dress!!!
    I love Chicago and have never had enough time to spend at the Art Institute. I think I could spend days there alone. I love it that much
    A great place so much fabulous food fantastic boutiques and art!!
    Do yourself a favor and plan to go back for a few days. You already have a great tour guide
    You made an elegant duo for the party

  12. That dress was the perfect choice. You look beautiful in it. And I love the gold shoes with it. Chicago is my favorite city, probably because I live only about 90 minutes from downtown. It’s so beautiful, and such a great place to eat and shop. Glad you had a great weekend!

  13. Glad you had a great weekend. Chicago is truly a wonderful city and so much to do and see. You looked beautiful and the dress seemed perfect!

  14. You look stunning. I love everything you chose and it all looked perfect on you! Sounds like you had a lovely weekend. Merry Christmas!

  15. Beautiful photos of your trip to Chicago! Thanks for sharing them with us. Since you’ll soon have an “empty nest” (sorry!!) you would be able to tag along with Paul on some of his business trips. He can work, you can explore the city and shop and eat, then meet up again in the evening!! You looked beautiful in your dress, shoes and accessories. All perfect choices.

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