Live like a Local: 5 Winter Chicago Activities

It's common knowledge that Chicago is a hot spot for fun activities in spring and summer. Rib Fest? Air and Water Show? Taste of Chicago? Sign me up!

Once things start to cool down, though, the selection starts to dwindle, and it seems there are less opportunities for outings and activities. Fear not! You're not doomed to spend the winter months indoors!

Are you looking for fun winter Chicago activities? AptAmigo has compiled a list of 5 fun local alternatives to traditional tourist spots. Read on to see some of the best things to do in Chicago winter!

Tourist Attraction: Randolph Street Market Festival

Local Attraction: West Town Winterfest

When: December 10, 12pm-6pm

What: A melange of many different festival classics; shopping, a raffle, a trolley tour, and an after party just for grownups!

Why It’s Great: Located in cozy, trendy West Town, this Winterfest skips the hustle and bustle of many Loop-area tourist attractions without sacrificing the electric Chicago atmosphere or the beautiful Chicago scenery. Attendees can choose to walk or climb aboard the Jolly Trolly, a 3 hour guided tour that covers all of the shoppable blocks that the festival has to offer.

Additionally, those who attend are invited to the Division Street “Naughty List” After Party Stroll, where they don their best holiday gear and head out to some of West Town’s best bars and restaurants after dark.


Tourist Attraction: Magnificent Mile Lights Festival

Local Attraction: Christmas Around the World at the Museum of Science and Industry in Hyde Park

When: Opens November 17

What: A bundle of over 50 Christmas trees, each representing different cultures and holiday traditions from around the world, surround a 45 foot-tall Grand Tree.

Why It’s Great: While for die-hard Christmas fans braving the frozen tundra of Chicago to view the gorgeous trees in along the Magnificent Mile is no big deal, this indoor display of trees appeals to both those who would brave an ice storm for tree-seeing and those who would prefer to keep their extremities while enjoying some winter fun in Chicago. At the end of the day, this attraction is for anyone who loves Christmas trees!


Tourist Attraction: Horse-Drawn Carriage Ride

Local Attraction: Sprint CTA Holiday Train

When: November-December, check schedule for exact line dates.

What: A six-car CTA train dressed to the nines for the holidays; on board, Santa and his elves pass out candy canes and give season’s greetings.

Why It’s Great: A great option for those who can’t splurge on a horse-drawn carriage, but who are still totally crazy about holiday-themed transportation and winter fun in Chicago. Beyond that, anyone who feels like they need a little extra push to get into the spirit will find it as the Holiday Train rolls into the station.


Tourist Attraction: Christkindlmarket

Local Attraction: Mercado Navidadeño at the National Museum of Mexican Art

When: November 25-November 27, 10am-4pm

What: A holiday market at one of Chicago’s many rich museums.

Why It’s Great: While most Chicagoans and Chicago tourists are used to the German-influenced Christkindlmarket, the Mercado Navidadeno brings another culture to the forefront. This small-scale market will allow tourists and locals alike to explore Christmas from another perspective.


Tourist Attraction: Hot Chocolate from Christkindlmart

Local Attraction: Tamales and Champurrado from a local cart

When: Most days

Where: Place differs

Why It’s Great: As a city with a large Latinx/Chicanx population, the tamale and champurrado cart plays a vital role in the winter mornings of many Chicagoans. While it might take a little wandering and research to track one down, the experience of warming your hands on a bag of fresh tamales and warming your belly with a hot cup of champurrado is an experience to which all true Chicagoans can relate.