Yes, we’re still thick in the middle of winter, but doesn’t it feel like we’ve turned the corner at least a little bit now that we’re into the new calendar year? And if you’re someone who doesn’t enjoy traditional winter activities like skiing or snowboarding, you’re probably counting the days until spring arrives.
The good news is that there are still plenty of things happening around Chicago to make the rest of winter feel a little less long. From food-focused events and cultural festivals to live performances and major sporting events, there’s no shortage of ways to get out of the house before winter officially wraps up on March 20.
In this article, we’ve rounded up some of the most interesting events happening in Chicago for the remainder of winter 2026. Each event includes dates and a brief overview of what you can expect, along with links for more details if you plan to attend.
If this is your first time here, we’re the Ben Lalez Team. We’ve been selling real estate in Chicago for a long time, and staying connected to what’s happening across the city is part of how we serve our clients.
We hope you find something on this list that helps make the rest of the snowy season more enjoyable!
Events At A Quick Glance
| Date Range | Event | Neighborhood Focus |
| Jan 21 – Feb 1 | Puppet Theater Festival | Citywide venues |
| Jan 23 – Feb 8 | Restaurant Week | Hyde Park, Lakeview, River North, West Loop |
| Jan 24 | Whiskey Tasting Festival | Lincoln Park |
| Jan 24 | Polar Adventure Day | Museum Campus/Northerly Island |
| Jan 25 – Feb 14 | Lyric Opera: Salome | Loop/Civic Opera House |
| Jan 28 – Feb 1 | Boat Show | McCormick Place |
| Feb 5-15 | Theatre Week | Wicker Park, Lincoln Park, Oakbrook |
| Feb 7-16 | Auto Show | McCormick Place area |
| Feb 14 | Tequila Tasting Festival | Lincoln Park |
| Feb 20 | Winter Jazz Fair | Loop/Cultural Center |
| Feb 28 | Beer Festival | Near South Side |
| Mar 7 | Chicago Bagel Fest | Wrigleyville |
| Mar 14 | St. Patrick’s Day | Downtown, Beverly, Norwood Park |
| Mar 14 | Uncorked Chicago | Near South Side |
| Mar 20-22 | Villain Arts Tattoo Festival | Rosemont |
January 2026
Chicago International Puppet Theater Festival (Jan 21 – Feb 1)
This festival brings together puppet companies from Chicago and around the world for nearly two weeks of performances. Shows take place at multiple venues across the city, including theaters, cultural centers, and community spaces. Expect a mix of traditional puppetry, modern interpretations, and experimental performances, many of which are designed for adults rather than just kids. You can find more information at the Chicago International Puppet Theater Festival website.
Chicago Restaurant Week 2026 (Jan 23 – Feb 8)
Restaurant Week is one of the easiest excuses to eat! Participating restaurants across neighborhoods like River North, West Loop, Lakeview, and Hyde Park offer prix fixe menus for brunch, lunch, and dinner at set price points. It’s a chance to revisit favorite spots or finally try places you’ve been eyeing for a while. Reservations are strongly recommended, especially for popular restaurants and weekend dining. Check out all 550+ participating restaurants at the Chicago Restaurant Week website.
2026 Chicago Winter Whiskey Tasting Festival (Jan 24)
For whiskey fans, the Chicago Winter Whiskey Tasting Festival is one of the more social cold-weather events on the calendar. It’s built around sampling 20+ craft, small-batch, and well-known whiskies, and it typically includes expert guides on-site to talk through what you’re drinking. Tickets are almost sold out, so buy them quickly on their event page here.
Polar Adventure Day (Jan 24 and Feb 21)
What better way to get over your hate of winter than to try loving it? Polar Adventure Day is all about embracing winter instead of avoiding it. The event typically includes cold-weather activities, outdoor games, and family-friendly programming along the lakefront. There will be warming stations and indoor options nearby, so you won’t freeze to death. It’s a short but fun event that gives you a reason to bundle up and spend part of the day outside. All the event details for Polar Adventure Day can be found on their website.
Lyric Opera: Salome (Jan 25 – Feb 14)
Lyric Opera’s production of Salome runs at the Civic Opera House and offers a dramatic and visually striking night out. The opera, composed by Richard Strauss, is known for its intense score and bold staging. Even if you aren’t an opera fan (and we definitely recommend checking it out at least once), this is one of those productions that draws interest for its scale and atmosphere alone. Performances run on select dates, so check the schedule in advance on the Lyric Opera website.
Chicago Boat Show 2026 (Jan 28 – Feb 1)
The Chicago Boat Show takes over McCormick Place with hundreds of boats, marine gear exhibits, and interactive displays. While boating season feels far away in January, this event always draws a big crowd. There are also seminars, demonstrations, and kid-friendly areas, making it a surprisingly practical way to spend a winter afternoon. Find out more information on the Chicago Boat Show website.
February 2026
Chicago Theatre Week 2026 (Feb 5-15)
Chicago Theatre Week is one of the best opportunities each winter to explore the city’s theater scene. For ten days, theaters across Chicago offer discounted tickets to a wide range of productions, including dramas, comedies, musicals, and smaller independent shows you might not normally come across. Performances take place throughout the city, making it easy to pair a show with dinner or a night out. If you’ve been meaning to see more live theater but haven’t known where to start, this is a good event to mark on your calendar. You can find more information about Chicago Theatre Week here.
Chicago Auto Show 2026 (Feb 7-16)
The Chicago Auto Show returns to McCormick Place as one of the largest auto shows in North America. You can explore hundreds of vehicles, including new models, concept cars, and electric vehicles. Interactive displays and test drive opportunities are often available, along with family-friendly activities. Even if you’re not shopping for a car, it’s an easy way to spend a few hours indoors during February. And who doesn’t like seeing cool cars? Go to the Chicago Auto Show website to get all the details.
2026 Chicago Winter Tequila Tasting Festival (Feb 14)
The Winter Tequila Tasting Festival brings together more than 20 tequilas and mezcals for sampling. It’s designed for both tequila aficionados and people who just enjoy trying new spirits, and because it’s on Valentine’s Day, it’s become something of a date-night option for couples who prefer a tasting event over a traditional dinner. But don’t get too hammered before dinner! Tickets are on sale on their event page.
Chicago Winter Jazz Fair (Feb 20)
Hosted at the Chicago Cultural Center, the Winter Jazz Fair showcases local jazz musicians and ensembles. The event is typically free and runs throughout the day. Free jazz… why not? Click on the Chicago Winter Jazz Fair website for more information.
Chicago Beer Festival (Feb 28)
The Chicago Beer Festival brings together breweries from across the region for tastings, seasonal releases, and limited edition pours. This year it’s being held at The Field Museum and will run from 7pm to 11pm. It’s a popular event, so tickets often sell out in advance. Get your tickets at the Chicago Beer Festival website.
March 2026
Chicago Bagel Fest (March 7)
This festival brings together some of the city’s best bagel makers for tastings, vendors, and live acoustic music. You’ll find all kinds of bagels and spreads, along with a bunch of giveaways. Go to the official Chicago Bagel Fest website to find all the details.
Chicago St. Patrick’s Day Parade & River Dyeing (Mar 14)
One of Chicago’s most recognizable traditions, the St. Patrick’s Day Parade and river dyeing takes place downtown each March. The Chicago River is dyed bright green in the morning, followed by a parade that winds through the Loop. Crowds gather early, especially along the riverwalk and parade route, so planning ahead helps. Definitely a Chicago-specific experience that you have to see at least once. You can go directly to the Chicago St. Patrick’s Day Parade website for everything you need to know.
Uncorked Chicago (Mar 14)
Uncorked Chicago is a wine tasting event held inside the Field Museum, featuring dozens of wines from different regions. General admission tickets typically include unlimited tastings, while higher-tier tickets allow earlier entry and access to premium pours. There’s music playing and light food available for purchase, and you’re free to walk through parts of the museum as you taste. Check out the Uncorked Wine Festival website to find out event details.
Villain Arts Tattoo Festival (Mar 20–22)
The Villain Arts Tattoo Festival is a 3-day event and features tattoo competitions, live entertainment, and vendors selling art, prints, and tattoo-related merchandise. The event draws a large crowd and stays busy most of the day, so plan accordingly. Visit the Villain Arts Tattoo Festival website to get tickets and view show info.
Final Thoughts
Trust us, we know winter in Chicago can feel long, especially once the holidays are over and spring still feels far away. But this stretch from January through March offers more than enough reasons to stay engaged with the city instead of waiting it out at home.
Whether you’re checking out a performance, trying a new restaurant, or joining a crowd downtown for a major event, there really is a lot going on that can fill your calendar until the warm weather comes back.
And if the end of winter has you thinking about making a move or exploring a new neighborhood once the weather warms up, we’re always happy to have a conversation with you. Give us a shout if you want to talk about real estate, and until then, stay warm!
