I’m Dreaming Of A Chicago Christmas #LoveThisCity #cbias

As a transplant here to Chicago, I think I tend to appreciate the city a tad more than those who have lived her their whole life. For example, come Christmas time, I love driving around looking at Christmas lights:


As much as love this house, I am so glad I don’t live next to it or have to pay their electric bill! However, as somebody just driving by, it was an awesome house. We drive around the city and sing Christmas carols and enjoy everything.

Another great way is to enjoy the city. My family doesn’t spend a lot of time in Downtown Chicago, so when we go, it is a treat. This holiday season is no exception. Chicago knows how to do Christmas like no other city.


We had some fun with the lions at The Art Institute.


From there, we did some shopping on Michigan Avenue. (American Girl is on Michigan Avenue. We didn’t visit there this trip. However, Madison and I have attended a Mastercard Priceless Experience there before. I can only highly recommend a Priceless Experience after doing one ourselves. It was beyond awesome and I wrote about it on here when we did it.)


We also went to Millennium Park. We watched the people skating (the line was way too long for the kids to rent skates. My kids adore The Bean, so we had some fun playing over there too!





If you are in Chicago during the holiday season, Macy’s On State Street is also a must stop. The store is decorated so awesomely both inside and out.



The kids even got to write a letter to Santa with Macy’s Believe program. Their letters earned Make A Wish an additional $2! (For every letter to Santa taken to the store and put into their mailbox, Macy’s donated $1.)




The Daley Center and the Christkindlmarket Chicago is another must stop! This is a German Christmas market, and they just have so many cool things to look at and eat! Do you go with the hot pretzels or the potato pancakes? Decisions, decisions! Bill went to Germany when he was in high school. We actually found a booth from where he bought coo coo clocks in Germany. It was the same shop, and we found the clock he bought. I’ll even admit that was pretty cool. Plus, it is held in Daley Center, so there is also the Christmas tree and Nativity scene.





A bit of comic relief is this next picture. This is the eternal flame. However, the pigeons in Chicago found a good way to keep warm! (Will also felt the need to walk up to every pigeon he saw and yell boo. There are a lot of pigeons downtown.)


Have you heard of Garrett’s Popcorn? This is another must stop. It is the most addicting popcorn you will find in the city. You literally cannot stop eating it until you eat all that you bought. We bought a 2 gallon tin ourselves.


I love finding a random guy carrying a huge present down the street.


Our last tradition is a unique stop. Every time we leave downtown, we stop and eat at Connie’s on the way home. It literally is the best pizza in Chicago. It is one of our favorite tradition.



You know you’ve have a priceless experience when this happens on the way home.


What does Chicago mean to you and your family? What are your favorite city traditions and experiences?

I am a member of the Collective Bias®  Social Fabric® Community.  This shop has been compensated as part of a social shopper insights study for Collective Bias®  and MasterCard #CBias #SocialFabric #LoveThisCity


  1. How fun! I have never been to Chigago but I would love to go.

  2. What a fun trip around the city. I've never been to Chicago, so thanks for the pictures as they were nice to look at.

  3. what a wonderful experience. I've never been to Chicago and I hope to experience that too!

  4. I have wanted to visit Chicago for years now, simply for the food experience alone. Love your tour and it looks like you all had a wonderful afternoon!

  5. Great pictures!

  6. I visited Chicago in 1999 and was impressed. Hope I get to go back some day.

  7. that looks like such a good time! i guess he was worn out from all the pigeon booing.

  8. Thanks for the tour of Chicago, I've never been there.

  9. Great pictures and it looks and sounds like you all had a great time! Wonderful family memories!

  10. Those are some great photos!

  11. thequirkymomma :

    I've been to Chicago twice, and both times were a riot!

  12. Wow I love the photo with the lights. I visited Chicago once and loved it

  13. I still haven't been to Chicago, but this is one city on my "to visit" list.

  14. I love that popcorn! I have my uncle bring some back for me every time he goes to Chicago.

  15. rebelchickjenn :

    I've always wanted to travel for Christmas but my family never lets me. Chicago looks amazing at Christmastime!

  16. I've never been, but this post makes me want to go :)

  17. What a fun family day! I've never been to Chicago other than an airport stopover but I'm headed there this Summer so thanks for some great tips!

  18. wow look at all the stuff there is to do Downtown I had no idea any of that stuff was down there. Thanks for sharing

  19. I've never been to Chicago, but it is on my must see cities list! :)

  20. I've been to Chicago twice but haven't been during Christmas. It looks beautiful.

  21. These are great photos!

  22. I've never been to Chicago but it looks like an amazing city.

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