Thinking about a trip to Chicago but afraid of big city prices? Well worry no more! Mr. Bug and I just got back from a weekend in Chicago and are happy to report there is a plethora of budget-friendly choices in this magnificent city. Here is our list of the top 5 free things to do in Chicago in winter.

Walking Tour

My absolute favorite way to check out a new city it to get out and just walk around. This gives us a chance to familiarize myself with my new surroundings. And if you ask me, there’s no better way to do this than by taking a free walking tour. Almost all major cities now have these, just google and see what you can find. While in Chicago, we did two separate free walking tours with Free Tours by Foot. We were able to see all the major sights within the Loop for “free” all while the tour guide provided vast knowledge on the city’s history and architecture. Do keep in mind it’s a pay-what-you-think setup so do please tip your tour guides as they do provide a phenomenal service.

Chicago River

Chicago Riverfront

Lincoln Park Zoo

Who doesn’t love a good trip to the zoo? Every time I go I feel like a child again. The Lincoln Park Zoo covers 35 acres and has various exhibits including polar bears, big cats, gorillas, reptiles, and just about anything in between. There is no charge for entry. If you go in the winter, make sure to check out Zoolights where the entire zoo is transformed into a winter wonderland with beautiful lights, Christmas music, and live ice carving.

Chicago ZooLights

The Magnificent Mile

Take a stroll along Michigan Ave and enjoy window shopping while walking among the beautiful skyscrapers that Chicago is famous for. I recommend a stroll beginning along the River Walk onto Michigan Ave and walking all the way down to North Shore Drive. Obviously you could break the bank easily while shopping at any of the numerous stores and restaurants, but window shopping is free and so much fun. Mr. Bug and I visited in December and the window fronts were all decked out for the holidays.

The Magnificent Mile

Millennium Park

A trip to Chicago wouldn’t be complete without a visit to the architectural piece Cloud Gate, lovingly nicknamed the “Bean”. Cloud Gate is located within Millennium Park and is a must-visit. The view reflected off of the Bean changes constantly depending on the weather. There is an ice skating rink that offers free skating if you have your own skates, or $12 to rent a pair. The park also hosts free concerts and movies at the Jay Pritzker Pavilion in the summer months.

Iceskating at Millennium Park


Mr. Bug being German and all, we simply could not visit Chicago and not stop by one of the largest German Christmas markets in the US. Christkinidlmarket is set up in Daley Park and has numerous vendors set up selling homemade gifts and trinkets such as ornaments, steins, and clothing. You can also get numerous authentic German dishes such as bratwursts, fried potatoes, and giant pretzels. But, a trip to a German Christmas market would not be complete without some Glühwein, which is mulled wine that is served piping hot in souvenir mugs. They also have German beer and chilled wine if you prefer. Make sure to visit the tent which is heated and has seating. If you’re lucky, you may also get to sing along with the live polka band that plays in the tent. Warm up from the cold with a warm beverage and singing along to the holiday songs. Entrance to the event is free if you simply want to walk around and feel like you stepped into Germany without leaving Chicago. Do keep in mind that food, drinks, and gifts/trinkets are additional so plan accordingly.


We had a fabulous time in Chicago and are already planning a return trip. We hope to return next time in the summer to check even more free events off our list. For those of you who have visited Chicago before, what are your favorite events, sights, and must-dos? We would love to hear your suggestions. Let us know and help us with ideas for our next stay in the Windy City.

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