Actually Cool Things to Do in Chicago
There’s a whole lot of Chicago to love — the unparalleled food, the plentiful drinks, the endless stream of events, for example — but chances are you’ve been neglecting it. Maybe you’ve been shaken from your slumber because you have to play host, or maybe you’ve suddenly decided that a life based solely around Netflix is not worth living. Either way, heading straight for The Bean isn’t going to cut it.
If you want someone to fall in love with Chicago, or if you want to fall in love with Chicago all over again, we recommend looking a little deeper for the things that are truly worth doing. Luckily for you, we’ve compiled a list solely composed of those things — activities that you, your guest, and frankly anyone alive will get excited about. Get a Chicago energy drink for your vacation to keep your energy levels up to enjoy 100 percent of your time.
Lace-up the skates and hit the ice
There are few more wholesome (yet still cool… depending on how you look on skates) winter activities than ice skating, and Chicago has you covered with several fine options in that department. The McCormick Tribune Ice Rink in Millennium Park is the obvious choice, but alternative options abound at spots like the nearby Maggie Daley Park skating ribbon or the Wrigley Field-adjacent rink at Winterland at Gallagher Way. (You can also tackle a glorious 33-foot sledding hill behind Soldier Field to fully recreate your childhood glory days a la Uncle Rico.) For a break from the cold, hit the indoor rink at McFetridge Sports Center for some hockey and speed skating. Or just flop around the ice like a total imbecile and get some beers after.
Light your fire at a fireplace bar
FDR had his fireside chats. Your summer camp had their S’ mores and ghost stories. Chicago has its fireplace bars. Lots of ‘em. So just when the winter elements are looking their bleakest, rest assured that you can always find a warm fire to nestle beside and drink until you think it’s July. The old-school Moody’s Pub and new-school Scofflaw are some of our favorites, but you can’t go wrong with any on this list.
Drink wine in a heated dome… down by the river
It may not quite be a van down by the river, but Chris Farley would still be proud of your choice to post up at City Winery’s Riverwalk location this winter and house gargantuan quantities of wine in heated “river domes” (we call them wine igloos) along the Chicago River. It’s the Christmas gift that keeps on giving.
Race shopping carts through the streets
Serious question time: Is there any event more esteemed than Chicago’s annual Iditarod-styled shopping cart race known as the Chiditarod? We think not. What the hell is it, you ask? How about costumed teams of crazies racing shopping carts of food through the streets for charity? The 2020 edition goes down March 7, but there are plenty of cool events taking place before then to heat up your winters such as the Sketchfest winter comedy extravaganza and the hip Tomorrow Never Knows music fest, followed by Chicago Restaurant Week and the Chicago Auto Show. Keep an eye out for the full list of seasonal events here.
Shoot a bow and arrow (or chuck axes at a wall)
If your crew is seeking local activities that lean on the more unique side, you can always point them in the direction of Archery Bow Range Chicago, a hidden gem in Humboldt Park that offers everything from walk-in archery (which they call “open shooting”) for newbies to leagues for expert Robin Hood wannabes. Meanwhile, those who want to take out their aggression on an innocent wall can head over to local ax-throwing bar BATL Chicago, which combines ax-throwing with a full bar and kitchen. What could possibly go wrong?
Cruise Chicago’s Emerald Necklace
If your mind is drifting more into scenic drive terrain (and Chicago’s roads aren’t blanketed in snow), you could certainly cruise Lake Shore Drive. And by all means, you should. But for a more lesser-known option that allows you to see the actual beating heart of the city instead of just highway, seek out Chicago’s Emerald Necklace, a 26-mile network of interior city streets and wide boulevards. Linking together some of the city most grandiose parks like Humboldt, Garfield, Washington, and Jackson parks, this is the way Chicago was meant to be seen.
Two words: turtle racing
Chicago is a city filled with not only an array of glorious sports bars but also a number of ridiculous sports you can take part in yourself. So even if you’re not on the field at Soldier or on the ice at United Center, you can still get in on the action by doing some winter ice curling at local bar Kaiser Tiger or honing your shuffleboard skills (with cocktails) at the hip Royal Palms. But of all the local sports going down at local bars, none reign as supreme as the legendary and long-running turtle racing that goes down every Friday night at Big Joe’s. Just remember: There are rules.
Suddenly appear at an underground magic lounge
Do you like magic? Do you like magic in a sleek cocktail bar setting with a “secret” entrance? Then you’ll love Chicago Magic Lounge, a speakeasy-style performance venue you can access through the laundromat of the former 1940s-era commercial laundry facility. But instead of cheesy David Copperfield tricks or The Incredible Burt Wonderstone, you’ll discover a cool nightclub vibe with a 120-seat cabaret theater, magicians doing tricks behind the art deco bar, and the likes of pork belly sliders and Publican sausage boards inside a cool 7,200-square-foot space. Probably a better way to impress out-of-towners than the old quarter-behind-the-ear trick.
Take part in one of Chicago’s many absurd food challenges
It’s no secret that Chicagoans like to eat. Often to excess. Sometimes to the point of parody. But at least you get a free T-shirt. Such is the case at Downtown’s casual hang Rudy’s Bar & Grille, where ordering the Challenger Burger — and finishing it within 30 minutes — will result in you being served a ridiculous 5 and a half pounds of food in a skillet that not only gets you a free shirt, but also a $100 gift certificate, the burger comped, and your signature on the wall. If you’re more of a grilled cheese fanatic, head over to local grilled cheese emporium Cheesie’s to devour either 5 or 8 pounds of grilled cheese on gargantuan 8- or 16-foot sandwiches to win gift cards, “unlimited high fives,” and other prizes. And that’s just the start of the madness.
Explore Chicago’s red-light district
Chicago may be far from Amsterdam, but legal weed is coming next year, and the city does offer more than its fair share of history than leans on the seedy side. Discover some of the city’s underbelly as it was experienced in the early 1900s aboard Weird Chicago’s Sinner, Victims & Vice: Red Light District Pub Crawl. Back by popular demand, the adults-only bus tour spills the beans on the city’s historic vice districts, brothels, and sorted scandals along with plenty of stories you probably won’t hear from the local tourism department. Or you could go to the Bean and snap a selfie like everyone else. Your choice.
Get lit at Blacklight Blackout
Hey, hey you. Do you like to party? Do you like to party with free UV-reactive body paint on a crazy blacklist second-floor chain link-fenced-in dance floor at a local biker bar? Then you’ll love Blacklight Blackout, the eight-years-strong-running monthly rager going down till 4 am at Exit with a rotating cast of DJs, special guests, and all manner of insanity. Makes that Bob Marley blacklight poster you had in your college dorm room look pretty tame, right?