This past weekend we drove four hours west to the windy city! Since this amazing city isn’t too far, I have been able to visit many times. Nick and I spent a weekend around Christmas time in Chicago four years ago, shortly after we started dating. Everything we experienced together during that season of butterflies and first together was magical and our trip to Chicago was nothing less. We ice skated, took long walks in the park, ate at cozy restaurants, made a fort in our hotel room and even ate ice cream in bed haha. Needless to say, that little trip has always held a special place in our hearts and inspired up to visit a festive city every year around the Holidays!

This year’s trip was extra special because our dog Leo tagged along for the first time. When we first arrived in the city, there were loud sirens that scared Leo as we drove to our hotel. It was probably our fault for leaving the windows down in the car, but the sound became intense quickly and Leo nearly jumped on my lap! Despite all the action and change of scenery, Leo adjusted to the excitement quickly and was walking around like a local by the afternoon.

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We checked in to Staypineapple Chicago – an iconic, dog-friendly hotel in the heart of the city. The friendly staff helped valet our car and get all of our bags (and Leo’s fan that he doesn’t travel without) to our room. In the room, we were greeted with sparkling water, champagne, and chocolates, aka the way to my heart. Leo loved looking out our window at the people below and jumping on the big comfy bed.

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I found the main stairwell of the hotel to be so stunning! We read that each of the colorful tiles were placed by hand many years ago when the building was constructed.

Millennium Park was a quick walk from our hotel and although Dog are not allowed in the park we still snapped a quick picture in front of the huge Christmas tree. Just a block away is a designated dog park, where we took Leo for some playtime. The dog park was small and had turf instead of grass which was super nice to keep the dogs clean and close by. We knew going in that the biggest challenge of this trip was going to be our limited restaurant options since it was too cold to eat outside on any dog-friendly patios. Thankfully, many restaurants offer delivery, so we ended up having Giordano’s Chicago style deep dish pizza ordered to our hotel room for dinner the first night and Wildberry pancakes for breakfast in the morning. We missed the experience of visiting these restaurants that we love but you also can’t complain about eating yummy food in your pajamas.

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We kicked off our second day in the city by walking around, taking photos and popping into shops. The Chicago Theater was also a short walk from our hotel and we could even see the sign from our room. I may or may not have planned out this red pea coat to take a photo in front of the sign…#noshame. Macy’s was practically right across from the hotel which made it easy for us to admire the outside décor and even take Leo inside to write his letter to Santa! We walked down by the Riverwalk and enjoyed the slower foot traffic. After hours of walking, we went back to the hotel for some downtime in the afternoon.

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That evening we dropped Leo off with a dog sitter and headed to the Christkindlmarket. I’ve been to this market several times and remembered it being busy and filled with the sweet smell of honey roasted almonds. This year it was so packed that you could hardly move and the lines to get up to the shops had to be at least a 30-minute wait. We squeezed our way through the crowd to the almond shop which I sadly couldn’t smell to find that they were only accepting cash, which we weren’t carrying. So that was a bit of a fail but at least it makes a funny story. We then went to The Dearborn Tavern for a drink and a bit to eat. We sat at the bar to be served quickly and enjoyed the atmosphere. We spent the rest of the evening walking around, playing cards while enjoying a beer at The Game Room, and grabbing another bite to eat at Chipotle. We found ourselves at Chipotle last year in NYC, so we think we may have started a new tradition of eating at Chipotle when in a big city despite all the unique, local options. Haha 

We picked Leo back up at the end of the evening and called it a night. The next morning, we slept in a bit, backed up, checked out, grabbed a bite to eat and hit the road so that we could get back at a decent time to get around for the week ahead. Our trip to Chicago was short and not as eventful as our visit a few years ago but I honestly feel like it was the perfect amount of time. We left with our holiday spirits high and with fun memories to add to our little tradition. What city do you think we should visit next year around this time??