Chicagoans are known for getting through the dreary, unending winter by telling themselves that “it’s a completely different city in the summer.” While that may be true, there’s still plenty of world-class entertainment and culture offered in the midst of the coldest season of the year. Some of those attractions aren’t just fun, they’re also free. With predictions of a colder and snowier season than last year’s relatively merciful winter, it might be a good time to start looking for things to do over the next few months. Even though many isolate themselves to Netflix and delivery, there’s no reason why the winter months should hinder you from exploring the city, even if you’re on a tight budget.

photo by Ben Miller / CC BY-SA


A Chicago staple, the Christkindlmarket is an outdoor market modeled after the German market of the same name. Located in Daley Plaza, it features vendors from around the world selling toys, beer, baked goods, and any other Christmas item you can imagine. Some vendors come from as far away as Austria and the Ukraine, but many others are Chicagoland small businesses. There are also Christmas choirs and a Santa house, making it one of the go-to holiday events for families in the Chicago area. The market opened in mid-November and will stay open until Christmas Eve. Make sure you take a walk through this Christmas oasis before it closes until next year. Oh – and don’t forget to grab mulled wine in a collectible ceramic boot mug.

photo by Chicago Architecture Today / CC BY

Jane Addams Hull-House Museum

One of the hidden gems of the city, the Hull House gives a truly unique perspective on immigration and suffrage. Jane Addams spent her life in Chicago where her work at the Hull House, as well her writing and activism, made her the second woman to win a Nobel Peace Prize. The Hull-House Museum is free and celebrates and honors Jane Addams and her accomplishments. It’s an incredibly underrated attraction in Chicago, one of the most powerful museums the city offers, and a part of Chicago history that is criminally underused. The museum also offers classes and other community outreach programs that continue Jane Addams’ storied legacy.

photo by Marit and Toomas Hinnosaar / CC BY

Lincoln Park ZooLights

The Lincoln Park Zoo is one of Chicago’s preeminent free attractions, especially in the summer. While a zoo might not sound like a great winter night out, during December the zoo puts on a magnificent show before many animals go inside for the winter. Throughout December and into January, the zoo covers its walkways and exhibits with colorful holiday lights. It’s truly one of the most unique and vibrant ways to get into the holiday spirit. At times, you can even forget you’re in the urban center of Chicago and have transported to a children’s holiday paradise. Besides the animals and lights, there are crafts, photos with Santa, and train rides for kids, while adults can enjoy warm wine or cold lager.

photo by Google

Intuit: The Center for Intuitive and Outsider Art

Henry Darger was a hospital custodian in Chicago for most of his life, but he’s now joined the ranks of artists made famous after their deaths. It would make sense then that most of the massive collection of multi-media art and writing found by his landlord after his death would be displayed in Chicago. Intuit features a permanent collection as well as various rotating exhibitions and galleries of other artists besides Darger. Most notably, the museum features a re-creation – with many of the same objects – of the reclusive Darger’s single-room apartment. The museum also offers a creative space for students and working artists, presenting contemporary and mixed-media installations that struggle to find a home in more traditional art galleries. Intuit is a free gallery, but does have a recommended donation of $5.00 for anyone over twelve.

photo by Alanscottwalker / CC BY-SA

Maggie Daley Skating Ribbon

This winter ice rink is not your traditional skating experience. The incredible views of the iconic Chicago skyline is only one of the main attractions for visitors. More than anything though, the ribbon-like shape provides a much more original experience for skaters. Instead of a basic oval like most skating rinks, this one is a quarter-mile long, making it one of the most popular and unique rinks in the city. Enjoy amazing views while leisurely gliding through Grant Park, a great time for families and friends. The rink runs until early March, weather permitting. Admission is free, but skate rentals are $12-$14 if you don’t bring your own pair.