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Guide to Spending Christmas and/or New Year’s Eve in Chicago with a Dog

January 15, 2020

Christmas time in Chicago is a magical winter wonderland with all the holiday cheer, glowing festive lights, parades, ice skating, giant lit trees, and German Christmas markets. If you are planning a trip with your dog in December, which I highly recommend, there are many dog-friendly festive activities you can experience together.

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The lighting of the Christmas Tree of Chicago begins the Christmas celebration in Chicago, the evening before Thanksgiving. We don’t attend the lighting event because it gets insanely crowded. This giant real tree is in Millennium Park and free to attend like the rest of the park. Unfortunately, dogs aren’t allowed in the park, but the Christmas tree is on the edge of it near Michigan Ave so you can still see it very well from the street. I wanted to take a closer picture for you all with Coco and luckily no one said anything to me as I walked into the park. We didn’t want to cause any issues so we didn’t stay long.

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Just behind the giant Christmas Tree in Millennium park lies the most iconic structure in Chicago, the Cloud Gate Sculpture, or to what most people know as the “bean.” The sculpture is made with highly polished stainless steel plates and captures the stunning Skyline of Chicago! Even if you have your dog I strongly recommend you have your friend watch the dog out of the park so you can check it out. You just shouldn’t miss this masterpiece!

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Just a 15 minute walk from Millennium park is the largest German Christmas market in Chicago, Christkindlmarket (go HERE for more info). Because it’s the largest and in the heart of Chicago, it get’s very crowded, especially on the weekends. We went a few different times (it was free) on the weekend and it was so packed with people I had to carry Coco and we didn’t get to see what most of the booths had to offer. Go during the week days for the best experience. This market runs until 4:00 pm on Christmas eve but another Christkindlmarket in Wrigleyville (my favorite) is much less crowded and runs until 4:00 pm on New Year’s eve!

Before heading to Wrigleyville, take a walk up Dearborn street until you run into the river, take a right and stop at City Winery and enjoy a drink on the river with your pup.

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City Winery

After your drink, continue walking east on the river and cross the DuSable Bridge on Michigan Ave. to find a very beautiful Christmas tree.

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Where you are standing is the start of the famous Magnificent Mile. Continue walking north on Michigan to explore all the shopping on Magnificent Mile. Many of the shops are dog friendly including the mall (Shops at North Bridge), Nordstrom and Nordstrom Rack, TJ Maxx, Bloomingdales, many high-end shops, etc..

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If you still have time that night head to Wriglyville to explore the another Christkindlmarket. Make sure you check the opening hours here. As you can see, even on a Sunday night, it was much less crowded so we actually got to experience everything the market had to offer. We saw many adorable pups in sweaters on a leash sniffing their way through the market.

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The Christmas market is located right at the Cubs stadium in Wrigleville and was, again, free of cost!

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The German market was so dog friendly they even had booth offering free “puppacinos (whipped cream for dogs).”

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The Raclette (Swiss cheese they served on bread) smelled amazing!

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Mulled Wine is always the one thing I look for at a Christmas market. It’s hot red wine mulled with spices and very delicious. I don’t see it much in Chicago so I was so excited a booth was selling it!

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For a dollar more it came with a cute boot shaped keep-sake mug. Each Christmas market had their own mug specific to their neighborhood.

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The booths had some really great stuff! These adorable Santa’s were my favorite.

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These painted ornaments were a big hit and would make perfect gifts.

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In the market there is also an ice skating rink for your friends and family to enjoy.

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They also have skate rentals and bag check (perfect for backpackers)!

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There were so many cute Instagram worthy decorations.

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How adorable is this giant Christmas bear?

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Another beautiful real Christmas Tree with gifts was located just outside the market.

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Happy Camper

At this point you are probably wondering where you can get some dinner in a warm place with your dog. Luckily, I have just the place in Wrigleyville just a few blocks from where you are. Happy Camper has a dog friendly outdoor area connected to it that has a temporary enclosure for the winter, so it’s pretty much like being inside and just as warm. Also they decorate like CRAZY for Christmas, like many of the bars in Wrigleyville.

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Happy Camper has a really cute Christmas themed area inside if you can have a friend watch your pup so you can get some pictures.

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This one was my favorite.

There are many Christmas themed bars in Chicago, especially in Wrigleville. I think that Wrigleyville is the best neighborhood to visit during Christmas and New Year’s eve.

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Santa Baby Bar outside area

Santa Baby Bar was one of my favorite Christmas bars. Because they serve food you can’t bring your dog inside but if you get a nice guy outside, he may let you take your dog to the outside area. If not you can still see the outside area from the street and take pictures.

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Santa Baby Bar 2018

Although you can’t bring your dog inside many of the Christmas themed bars/restaurants I highly recommend you leave your dog at home or have a friend watch him for a few hours. I felt like I was at Santa’s workshop in the North Pole. It was a magical experience!

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Santa Baby Bar inside
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Santa Baby Bar inside
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Elf’d Up Bar
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Rudolph’s Bar
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Rudolph’s Bar
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Zoo Lights

I have to mention how incredible the Zoo Lights were, even though not dog friendly. Unfortunately, the zoo doesn’t allows you to bring pets. But again, I highly recommend leaving your dog for a few hours to see it. The entire zoo illuminates with more than a million lights and is FREE to attend.

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