Christmas Night Out in Wrigleyville

After being suggested to us by a friend we decided to head in to the Wrigleyville neighborhood in Chicago to check out the Santa Baby pop up Bar. Regularly the Bar -ups Bartending academy, they transform their location for Christmas each year. The website videos looked amazing and the decor inside definitely lived up to the hype. You can check out their site here. Once we got there we found that the majority of the street has been prepped for Christmas and had a lovely Christmas night out in Wrigleyville.

You can book tickets online for their brunch offerings or for their free entry after 4pm. They didn’t bother to check ours when we got their fro the free general admission but I would still book yours just in case. The entirety of the bar inside and out were chock full of gorgeous Christmas decor. To go along with the theme they have festive food and drinks on offer too. The drinks were definitely pricey with even the regular sized Christmas drinks being $13 a pop but they were definitely delicious. Unfortunately, when we went on a Sunday evening they were packed full and we weren’t able to get a table to try out the food.

There are a lot of fun photo props in the outdoor space if you are willing to brave the cold or visit on a milder night. It was way less crowded then the inside so we were able to play around more with the sets and find a spot to sit and have our drinks at the picnic tables.

We continued our Christmas Night out in Wrigleyville right across the street. We stumbled upon Santa’s workshop, normally known as Old Crow Smokehouse, check out their website here. It’s a much larger space that though slightly less coated in Christmas was also much less crowded. They still offer their usual drinks and food on the main floor. Plus, I got to live out my childhood dreams on the giant pony!

More Holiday fun is up on the roof where we got some hot drinks to keep warm and relax in some fireside seating. They had spiked hot chocolate and hot cider, we tried one of each. They were delicious and made with good quality liquors but were even more expensive then Santa Baby, $32 total for just the two drinks! If I hadn’t had some birthday money burning a hole in my pocket I really would have been feeling the pinch. When we thought more about all the free fun holiday decor, activities and photo ops included we did decide it was all worth it in the end.

No Christmas season is complete without a visit with Santa. After you’ve gone in the igloo to get your drinks you can head back out to brave the cold and visit Santa and his sleigh (did you spot his reindeer above?) You can sit with him and get some photos and of course tell him what you want for Christmas this year. Santa is what helped draw us into this location in the first place as he spreads his cheer to the street from his roof stop perch that can be seen from the street.

If you are looking to keep the party going afterwards, Sluggers bar is also nearby and it’s dueling pianos are a great night any time of year. Or if you’re looking to end on some more low key grub like we were, you can stop at the shake shack on the street for some burgers and shakes for the way home. Our Christmas night out in Wrigleyville was both Merry and Bright. We enjoyed some festive expensive drinks in a sparkling holiday atmosphere. We have a new holiday memory and the all kinds of fun photos to remember it for many christmases to come.