17 Places to Visit in Chicago this Winter – 2023

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17 Places to Visit in Chicago this Winter – 2023

Chicago. The Windy City. If you’ll be braving the Illinois winter and celebrating this holiday season amid Chicago’s famed skyline and eclectic mix of music, tastes, and sights – you’ll be pleased to know you couldn’t have picked a better place. And with so much going on, it can be hard to navigate this city. Fortunately, we’ve got you covered – read on for seventeen of our favorite places to visit in Chicago this winter.


Enjoy the beauty and charm of a continental European-style Christmas Market at Chicago Christkindlmarket! Here, visitors can stroll amid rows of cozy wooden stalls and enjoy fresh baked goods, hot beverages from hot chocolate to mulled wine, and shop gifts, play games and enjoy live music. Whether a festive family occasion or a great date night, Christkindlmarket is a Chicago favorite for good reason.

Millennium Park Ice Skating

Another fun tradition to the city is ice skating with friends and family in one of the city’s most famous venues – Millenium Park! Here in Chicago’s favored spot for community and home of the iconic “Bean,” you can skate the night away to holiday tunes and spend a good few hours with pictures on the ice. A great bit of active holiday fun and also a solid photo opportunity.

Navy Pier

Featuring a festive Christmas Village, a Ferris Wheel, a number of firework shows, shopping centers, games and other rides, Navy Pier’s appeal extends well into Winter with its many attractions. This is especially good for families or larger groups visiting Chicago this winter.

Blackhawks Games

One of the more electrifying and exciting events happening around Chicago during the Winter Season is the rare Blackhawks home game! Come don the Red, Black and White and join in on of Chicago’s most storied and esteemed sporting traditions as the Blackhawks defend their home turf of United Centre.

Northerly Island Winter Sports

Amid ice skiing, snowboarding, ice skating, sledding and many other activities, visitors will be pleasantly delighted in the range of Winter Sports options at Northerly Island! No need to travel as far as Aspen or the ranges of California when you can enjoy the thrill of Winter Sports here at nearby Northerly Island!

Lincoln Park Zoo Lights

A more calm alternative is a walk amid the Zoo Lights at the famous Lincoln Park Zoo. While many of the Zoo’s residents might have turned in for the Winter, the acclaimed light show and footpaths of the Lincoln Park Zoo come to life at this time of year. This is a great photo opportunity and experience for families as it is for date night and couples alike. 

Lakefront Trail Walks

Yet another beautiful walk to take on this winter are the series of trails along the Lakefront. With such a variety of sculptures, lights and artwork installations regularly joining the sights and events of this area of Chicago, this is another great addition to consider. (However, those who prefer the warmth of their car might also consider the many drive-through trails also available).

Chicago Symphony Orchestra

While you may hear the same holiday tunes at this time of year, every year, (nonstop, namely Mariah Carey) what you may not hear as often is the Chicago Symphony Orchestra! Superbly talented and putting on performances and concerts of holiday season classics – a trip to a CSO concert is an amazing experience for all who can make it.

Order in With Holiday Sales

While this might seem an odd one, with Chicago’s connection as a hub and many delivery and at-home services, sometimes the best winter nights are the ones spent at home. Sleep in and stay comfortable on the worst of winter nights and relish in the joy of hearty Chicago cuisine delivered to your doorstep. Enjoying a snow-in can be a great way to add a breather to your trip, as well as the extra comfort of those sleepy winter mornings. After all, who doesn’t sleep better under a warm cover when it’s a cold night?

Garfield Park Conservatory

Stroll amid the winter incarnation of this Chicago institution, amid seasonal foliage, ornaments, miniature Christmas villages and lights at the gorgeous Garfield Park Conservatory. Perfect for a date night or postcard photos from the trip.

Electric Garden

Enjoy the warmth and delights of a beer garden at this revamped Chicago venue, warming up on hearty ales and local fare. We recommend items such as the seasonal burgers or chimichurri nachos to sample some of the best in Midwestern produce, namely beef and dairy. 

Wrigley Field Gallagher Way Winterland

Come celebrate the Winter season at this iconic venue – Wrigley Field! Enjoy festive games, fresh and gourmet food, music, dance and plenty of vendors for gifts all at this one-of-a-kind location. Here, visitors can visit and tour a piece of Chicago history, as well as relish in the fun of a winter market. Come take pictures next to this giant of sporting history, grab a gift for the loved ones at home and enjoy plenty of games, music and fun here at the iconic Wrigley Field’s Gallagher Way Winterland. 

Magnificent Mile Lights

Another noteworthy light show installation are the Magnificent Mile Lights, a great attraction for those from outside of the country to get a taste of Chicago style winter lights and pageantry. During the eponymous festival, a great series of dance, song and captivating floats take the streets, while for the rest of the season, visitors can walk underneath illuminated trees and the romantic riverside.

Aire Baths

If you’re wanting to enjoy the Chicago Winter in style, why bother fighting the high winds, heavy snow and freezing temperatures when you could unwind in a warm bath? Come out of the Winter looking a bit younger and a lot less stressed when you relax at the Aire Baths, a growing favorite in Chicagoland. Here, an intricate system of different baths at differing temperatures and salinities will treat you right, all in the restored location of a former factory, now a ritzy spa. This is something uniquely Great Lakes, and you’ll thank yourself for every second you spend in the warm waters as opposed to battling the elements outside.

Drive-In Movie

Another warm alternative to duking it out with the infamous Illinois winters is attending a drive-in cinema! Bring your comfiest pajamas, thick blankets, and snacks with you to the drive in cinema and enjoy movies on the big screen, right from the comfort of your car! This is great for families to cozy up inside the van or suv, or as a uniquely comfy and down to earth date night idea.

Chinese New Year in Chinatown

Featuring an exciting mix of lion and dragon dances, massive drums, firecrackers, delicious Chinese fare and the color red galore, Chinese New Year in Chicagoland is something to witness! Frequently falling in late January or early February, this is a great way to engage with the Chicago community in a collection of festivals featuring daring physical stunts, martial arts, craftsmanship and last but not least, absolutely delicious Chinese dishes. Chicago’s Chinese-American community comes to life during this important holiday, and is a great way to enjoy pageantry, performance and community all out on the streets and squares of the Windy City. 

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