Where to Stay

We stayed at Voco Downtown. It was well located, convenient and the staff was extremely accommodating and kind. Another suggestion I would have is the Athletic hotel. Though I have never stayed here, we visited this hotel multiple times due to its incredible location and wide range of activities in the building that will be addressed on the next paragraph.

What To Do

Our first adventure began at the Lincoln Park Zoo with some truly breathtaking light displays. Admission is between $7-10 per person and they offer many drinks including peppermint hot chocolate and mulled wine.

Christkindlmarket was a great way to fulfill festive cravings with multiple unique booths from hand-painted ornaments to bratwurst to scarves, this market is small but mighty if you’re searching for a unique gift or just want to warm up with hot cider.

Circling back to the Athletic Hotel, you can find a speakeasy located inside called the Cherry Circle Room as well as a rooftop restaurant called Cindy’s overlooking the city with the Bean as a focal point. The alternative rooftops we attempted to visit were much too crowded and not worth the headache.

Fan of Ferris Bueller’s Day Off? Chicago is great for spotting the iconic scenes most notably the Art Institute of Chicago.

Taking a guided tour in a new city is, of course, a great way to learn about the history and significance. We decided to tour via boat, and it was such a fun and unique way to see Chicago with a funny guide and no unnecessary trekking.

The Navy Pier is another spot to add to the itinerary for shopping, walking, sightseeing, and ending at the ferris wheel for a breathtaking view of the cityscape.

Where To Eat

As Floridian’s we had to experience a true Portillo’s hot dog. If you want to feel local I suggest stopping by one of their locations and getting delightfully greasy with their iconic dishes.

For a holiday-focused outing, The Treehouse was decorated to the nines for Christmas and themed all of their food and drinks for a truly immersive experience that we conveniently stumbled upon. You cannot skip their Mac’n’cheese arancini balls!

For a more elevated (less budget-friendly) dining experience, Tao did not disappoint with divine sushi dishes and exceptional service.

Chicago also features a five-story Starbucks with a rooftop, espresso martini flights, and unique food you can’t find in regular shops.

Getting Around

Uber was our best option for further locations with no issues. When we could, we walked to most places with ease (as long as we were properly prepped for the intense wind chill).