How to Celebrate the Holidays in Chicago This Year

These are the best ways to spend the most wonderful time of the year.

Millennium Park
Millennium Park
Millennium Park

The holiday season is here in force, if you couldn’t tell from the fact that we’ve already had our first snow of the winter and all of the festive lights. The bad news is that means that those balmy 40 degree autumn days are gone. The good news is that our fair city has more than enough fun activities (both indoor and outdoor) to help you celebrate the holiday season in style.

Bring some holiday cheer home at one of Chicago’s Christkindlmarkets

The Christkindlmarket, Chicago’s best and largest holiday marketplace, has expanded and now boasts three locations: one in Aurora, one in Wrigleyville, and its flagship location downtown. All three will feature the traditional holiday handcrafts, sausages, pretzels, and Gl√ľhwein the market is known for, along with live music and entertainment. It’s a holiday tradition for a reason.

Bounce into the spirit of the season with some balloon art

Luft Balloons Chicago has given its Wicker Park retail location a holiday makeover, and is allowing visitors of all ages to come in and tour their balloon-filled Santa Wonderland. Employees will be on hand to help visitors snap the perfect selfie among the balloon art (a highlight is the balloon Santa), and your time there will also include a scavenger hunt and a discount on any balloon art you’ll want to pick up for your own holiday celebration.

Bathe in nostalgia with jazz covers of holiday classics

Streeterville’s favorite jazz destination Winter’s Jazz Club is getting in the spirit this year with a selection of holiday-themed shows up until Christmas, including a jazz trio tribute to A Charlie Brown Christmas, as well as a Christmas-Eve-Eve celebration featuring soulful covers of holiday classics. Tickets are available now, so dust off that fedora you bought in 2009 and have yourself a jazzy little holiday.

Celebrate eight crazy nights

However you spell it, Hanukkah usually gets the short end of the stick when it comes to holiday pop-ups and celebrations. Thankfully, Wrigleyville’s Graystone Tavern offers a welcome alternative to Santa Baby with their 8 Crazy Nights pop-up. Snap some photos at their ugly Hanukkah sweater wall, indulge in their boozy spin on classic sufganiyot (jelly-filled donuts), and round up a group of friends to perform what can only be referred to as a “menorah shotski.” Chag sameach.

Courtesy of Chicago Botanic Garden
Courtesy of Chicago Botanic Garden
Courtesy of Chicago Botanic Garden

Immerse yourself in twinkling lights

By far one of the most romantic activities you can do this holiday is take someone special to the Chicago Botanic Garden for their newly revamped holiday lightscape. Walk the path through the gardens and take in the art installations, including the fire garden and the classic Winter Cathedral. There are few better ways to take in the magic of the holiday than among the lights.

Experience a re-imagined holiday classic at The Marriott

Running through January 1, The Marriott Theatre is currently featuring a musical adaptation of A Christmas Story-adapted by the minds behind Dear Evan Hansen, La La Land, and The Greatest Showman. Why not celebrate the season with a show, let alone a show nominated for three Tony awards, including Best Musical? Tickets are available now, though availability is dwindling for certain show dates.

Have a headbanging holiday

A mainstay in any holiday playlist worth its salt, the Trans-Siberian Orchestra is playing back to back shows at Allstate Arena featuring their trademark metal arrangements of holiday classics. Pull those leather pants out of your closet and start growing your hair out now, because the shows are coming up soon.

Lace up your skates and take to the city

There’s no shortage of ice rinks in Chicago to show off your skating skills. On Ice, from the indoor McFetridge Sports Center to the rink at Millennium Park. Our favorite spot to skate, however, is The Ribbon at Maggie Daley Park, a winding loop that features some of the best views of the skyline. Take your pick, and then drop into a cafe to warm up with some cocoa. Holiday bliss.

Snap a selfie with the city’s official Christmas tree

Make the trek downtown to the corner of Michigan and Washington to bask in the glory of Chicago’s official Christmas tree, a 55-foot Colorado Blue Spruce. Although the lighting ceremony was back in November, the tree itself will be on display through early January, complete with painstakingly-placed decorations, lights, and ornaments. If you’re by the Magnificent Mile doing your holiday shopping, make it a point to stop by.

Get classy at the ballet

Depending on how your end-of-year finances shook out, taking part in one of Chicago’s best holiday traditions is a great way to ring in the season. The Joffrey Ballet, one of the world’s premier dance companies, is running their yearly production of The Nutcracker through December 27. And despite what you might think, it’s actually not that pricey to go see the show! Tickets start at $64 for weeknight shows, which is approximately the cost of a Grubhub Cheesie’s order for two.

Watch a holiday classic on a REALLY big screen

Pilsen’s ChiTown Movies has been keeping the drive-in film tradition alive since they opened, and they’re showing holiday classics all month, from Die Hard, to A Muppet Christmas Carol, to a Christmas Day showing of Home Alone. Enjoy the drive through the snowy city, crank your heat up, and celebrate the season from the comfort of your own car.

Traipse through a gigantic winter wonderland

A huge swath of Goose Island has been transformed into a holiday winterscape, courtesy of Jack Frost Winterfest. Play hooky for a day and indulge in some axe throwing, ice skating, and drinks courtesy of multiple full bars-and then wander through the Christmas tree farm to pick out a seasonal souvenir from your visit. These Goose Island pop-ups never disappoint, so make sure to check it out.

Brave the cold for a themed holiday run

The Hot Cocoa Hustle might be behind us, but for Chicago runners, there are still plenty of winter runs to take part in. Our recommendation is the officially licensed Charlie Brown Christmas run, a virtual race that you can complete on your own schedule. Bibs are available for 5ks, 10ks, and a 13.1 mile challenge-and include a bunch of themed swag including a beautiful hand-painted finisher medal.

Have a snow-free snow day at the Garfield Conservatory

For those of us who love winter, but hate what it does to Chicago’s vibrant plant life, Garfield Conservatory has you covered. Their winter flower show is currently open, themed after the feeling we all got as kids when we woke up and school was canceled due to snow. The exhibits will feature geraniums, poinsettias, pansies, and more in evocative arrangements of pink and white, evoking the fluffy, comforting textures of snow in the sun. As an added bonus, the delightful scents should be enough to break through even the sniffliest of sinuses.Want more Thrillist? Follow us on¬†Instagram,¬†Twitter,¬†Pinterest,¬†YouTube,¬†TikTok, and¬†Snapchat.

Sam Greszes is a contributor for Thrillist.


Robyn DaCultyre Is Doing It for the Culture

"The cool thing about Ohio is that there is literally a place for everyone."

Photo by Kayode Omoyosi
Photo by Kayode Omoyosi
Photo by Kayode Omoyosi

I was introduced to Robyn DaCultyre at an Untitled Queen show at C’mon Everybody in late January, and it was one of the most unique drag shows I’d seen in a while. Afterwards, I tracked down this self-described “drag creature” and video chatted about her drag origin story, the state of drag in her native Ohio, and the dual identities that make up her persona. Thrillist: I want to ask you about how Robyn DaCultyre came about and your point of view behind your performance.

Robyn DaCultyre: I’ve been travelling around the country from a young age in ministry and Christian studies. I moved to Chicago right after high school. Four years later, moved back to Columbus and decided I didn’t really want to do church anymore; that wasn’t where my heart was.

I had a really low point in my life and had a suicide attempt and then really found drag and started doing drag as a coping mechanism and way to let off steam. I started in July of 2019, and it was really a lot of punk and metal music. I created this drag creature of sorts and they were really out of this world and celestial and all of those fun alien type terms.

And then we went into a global pandemic and I had a lot of time to figure out who I wanted to be. Digitally I was still doing a lot of drag creature-esque numbers and all of that, but I had this moment where we’re on the front lines getting hit with pepper spray and rubber bullets and pepper spray-all of those lovely things. And I said, I have this platform and I need to start showcasing what’s happening.

Untitled [Queen] stepped in at the right time and messaged me and said, “I’m doing this show for Independence Day called Untitled in America with 52 different performers and I want you to be a part of it.” It was at that moment I was able to take the footage I had been recording on the front lines and incorporate it into digital content. I did a song called Black Like Me by Mickey Guyton that talks about white picket fences, but if you want to see how America is, then you should try being Black like me. The imagery of what’s literally happening in Columbus in that digital performance really spearheaded me into focusing on people who look like me.

Nina Simone is one of my biggest inspirations, and one of her quotes that resonates with me is that it’s the duty of the artist to resonate with the times. My art is politically charged. I like to entertain, but there will definitely be a time when you come to a show expecting to have your drink and be chill and that might not be the case.

How did the name Robyn DaCultyre come about?

I was smoking with Ursula Major, who was on season one of Dragula, and the first time I introduced myself to her I was Robyn Banks, which is my drag name originally. She said, “Well, do you just not want to be original at all?” [Laughs] And I sat with that for a couple of months, and I got really stoned one day and was listening to Janelle Monae, and she talks about doing it for the culture, and I said “I do it for the culture, too!” And the rest is history.

And you started a series called Melanated.

We started Melanated last February. I told the idea to my show director that there were no shows specifically run by Black people that only featured Black entertainers. I wanted to do this show for a night and she said, Why don’t we do it once a week for the whole month? The first show happens, and it’s a sold out crowd, and [my director] comes back and says we should do this every month. So I sucked it up and here we are a year later.

Melanated is the only fully Black show in all of the state. It’s a horrible marketing tool and not something I want to promote, but it is just a fact. It amazes me that we are the 13th largest city in America and there’s nothing here that’s fully focused on Black entertainers. The name also comes from Janelle Monae; she says she’s highly melanated and I said, that works.

Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)

You refer to yourself as a drag creature, as opposed to drag queen or king…

This is actually the first time I’m making this public. I am in this place where I want to separate the alternative creature from who this melanated goddess or whatever is. DaCultyre is definitely the person who runs Melanated and then Robyn is this drag creature that is out of this world and really loves punk and alternative music. And both intertwine to make Robyn DaCultyre.

You also do pageants. Tell me about that.

In 2020 I was appointed by Nina West, who is from Columbus, as the representative from Ohio for National Entertainer of the Year in Louisville, Kentucky. I placed ninth out of 13 contestants and I really fell in love with the system and fell in love with the pageantry and loved the idea of reigning and being different. I want to show that we as alternative performers, as bearded performers, you can come into these systems and shake things up.

Is there a uniquely “Ohio” style of drag?

No, and I think that’s one of the things that makes it so amazing is that everyone has their own unique style, and it’s all pretty much accepted. I started as a performer and a drag creature and there was space that was afforded to me and I transitioned to more glamor and pageantry and that’s afforded to me as well. I’ve been a bearded entertainer for a year now. The cool thing about Ohio is that there is literally a place for everyone.

I think I have everything I need. Is there anything else I didn’t ask you about that you want to bring up, or‚Ķ

I don’t think so. Are there any generic questions you haven’t asked?

Generic questions‚ĶI think I asked all of them already [laughs]. I like to ask what you’d be doing if you weren’t doing drag?

It’s a great question. I have a day job that is very demanding so I need drag to get away. I’m also very creative and artistic. I used to do web design and all these other things to pull into my creativity. Drag is the longest thing I’ve stuck with in all parts of my life, so I don’t think it’s going anywhere anytime soon.

Get the latest from Thrillist Australia delivered straight to your inbox, subscribe here.

John deBary¬†is a drinks expert and writer. His first cocktail book,¬†Drink What You Want, is available now, and his next book,¬†Saved by the Bellini, is expected in early 2023. He is also the co-founder and president of the¬†Restaurant Workers’ Community Foundation, which is dedicated to improving the lives of hospitality industry professionals through advocacy, grant making, and impact investing.


Our Best Stories, Delivered Daily
The best decision you'll make all day.