10 Chicago attractions that are even better in the winter
This downtown park is a gem of a public space no matter the season, but it transforms into an ice-skating haven come wintertime. The quarter-mile skating ribbon is the park's most appealing attraction, and it's open from November to early March. Cradled in the epic Chicago skyline, skaters can take in majestic views of the cityscape while zipping around the rink. It's free to use, but skate rentals cost $12.
This Hyde Park cultural hub is now one of the oldest African-American–focused museums in the country. On display are documents and artifacts from the lives of overlooked or unjustly marginalized movers and shakers, plus a collection of vibrant African-American art. The museum really comes to life in February for Black History Month, with an excellent slate of talks, dance performances and art presentations happening nearly every day of the month.
For movie lovers who don't care for traditional Hollywood blockbusters, there's no better theater than the Music Box, a two-screen cinema that shows the latest art-house films and documentaries. The stunning main theater regularly hosts director Q&As as well as weekly midnight screenings of cult classics. The best part? December, January and February are the best months to see a flick. Since it's awards season, all of the year's best movies are screening or being re-released for the occasion.
We don't need to tell you that the Art Institute is a must-see attraction in Chicago. What you should know, though, is that it's possible to visit AIC without dealing with the mobs of tourists the summer months inspire. Take in iconic artworks like American Gothic, Nighthawks and Seurat's A Sunday on La Grande Jatte in relative peace. Plus, Illinois residents will receive free admission on January 18, 19, 22–26 as part of Chicago Museum Week. We can't guarantee a quiet visit on those dates, but hey, free is free.
Okay, we can't endorse much about what Al Capone did, but the gangster sure picked a good place to drink. The Green Mill is a perfect place to curl up on a winter night—even if you're not sitting in Capone's favorite booth. With a great lineup of free jazz most nights of the week and the Paper Machete comedy show every Saturday, winter doldrums can't quell the Green Mill's enduring liveliness. Come early, as it’s usually understandably busy.
The conservatory is free and open 365 days a year, but in our opinion, its a perfect wintertime activity. In the thick of January and February, all we want to do is pretend we're somewhere else, and a trip to the conservatory offers just that. Described as "landscape art under glass" when it opened in 1908, the Jens Jensen-designed plant house boasts revolutionary architecture and one of the largest collections of flora in the world. Browse the Desert House packed with succulents, the jungle-esque Aroid House and the lush Fern Room to escape the cold.
Nothing thaws us out like a couple of beers and a whole lot of laughter. The Second City offers just that seven nights a week. Check out the theater's Mainstage or e.t.c. sketch revues, or pop into the Training Center stages to see some up-and-comers perform. No matter what, venturing out into the brutal winter to the warm embrace of the Second City somehow makes their sketch and improv even funnier. No wonder the likes of Bill Murray, Tina Fey, Amy Poehler and Stephen Colbert liked it here so much.
While it may be snowy and bitterly cold outside, it's always springtime inside the Peggy Notebaert Nature Museum. The 2,700-square-foot Judy Istock Butterfly Haven wields particular power during the frosty months, as it offers a dreamy (and warm) reprieve from the harsh elements. The rest of the museum is fantastic, too—bring the kids for the hands-on interactive displays; you'll learn a great deal about conservation along the way.
Want to get out of the house for dinner and drinks but can't stand the travel time between spots? Once you get to Thalia Hall, you won't have to step outside to enjoy an epic night. Start with dinner at Dusek's, the contemporary American restaurant attached to the concert hall, before getting post-dinner drinks at the basement bar, Punch House. Then pop up to Thalia Hall itself, a concert venue that was built in the late-19th century as a bohemian opera hall. Bands play the venue almost every night of the week, and bookings range from indie to Americana to psych-rock.
We recommend going to this venue in January, when blues legend Buddy Guy plays a residency at his own club. While he may have founded it, the venue has hosted everyone from Eric Clapton to David Bowie. Grammy trophies, worn guitars and Guy's signature polka-dot guitar straps line the walls, which serve as a display case for gifts and accolades the musician has received.