4 Unique Things to Do in Chicago when the Weather Sucks

Some days, Chicago looks like Ferris Bueller should be ditching one of his last days of school to commandeer a parade, all blue skies and happy, puffy clouds. Other days, Chicago’s weather can be… well, a bit of a jerk. While the Windy City enjoys some of the most glorious summers around, the weather can also  be pretty extreme, from muggy and scorching in the summer to you-can-feel-your-eyeballs-freezing cold in the winter.

So if you happen to be in Chicago when there’s heat, rain, or sleet and you’re looking for something different than the litany of Chicago’s world class museums (some of my favorite ones are the Art Institute of Chicago, the National Museum of Mexican Art, which is FREE! and the Chicago History Museum), here are four unique and awesome things to do in Chicago that will keep you dry and comfortable on a rainy, snowy, or cold day.

Hanging out in a doorway is one option to beat the rain, but let's see what else Chicago has up its sleeve.

Conjure Up Some Cocktails at the Chicago Magic Lounge

5050 N Clark St, Chicago, IL 60640

Monday through Wednesday 5–11 PM;Thursday 5PM–12AM; Friday and Saturday 5PM–2AM and Sundays 1-3 PM

Imagine wandering around a relatively non-remarkable city block, when you notice, out of the corner of your eye, a laundromat with a mysterious allure (... not something that happens all too frequently). Upon closer inspection, you find a stocky, suited man at the door, who asks you if you’re looking to do some laundry. “Sure”, you find yourself saying and stepping into a tight room, whirling with washers. “You can always call for help, if you need a hand with the laundry” the suited man winks at you, nodding towards the phone on the wall, before he closes you into the laundromat alone. As the washers hums around you, you hesitantly place your hand on the phone and pick up the receiver and…A secret door springs open and abracadabra- you have officially entered the Chicago Magic Lounge, a bar that is a little bit goofy, a little bit sexy and 100% fun.

I’ve been to many cities in many countries and have never been in a bar quite like this one. This speakeasy, which harkens back to Chicago’s glory days where dozens of magic performance bars dotted Chicago’s nightlife, boasts three distinct venues where magicians dazzle patrons with their tricks and sleights-of-hand.

Upon entering the venue, you are immediately welcomed into the art-deco inspired upscale Performance Bar, where you can sip on a swanky cocktail whilst your bartender performs card tricks and other illusions a couple of feet away. In the bar’s library (stocked with limited edition books written by magicians, of course), yet another secret door will whisk you into the bar’s 120-seat theater, where national acts dazzle audiences with their magic tricks with two nightly showings every Thursday through Saturday. I think the last time I saw a magic show was at Adventureland, Des Moines, Iowa’s Wild Western-themed amusement park, while sipping a lemon shake-up out of a plastic cup and shifting around uncomfortably on a cracked vinyl chair. The theater here couldn’t be more different, all low-lighting, sleek bars, and plush seats. Preceding the show, magicians mill around the theater and perform tricks at your tableside, while you get tipsy on carefully crafted cocktails- I highly recommend the Dark Arts, a rye-based drink with a hint of cherry sweetness. While we didn’t order any food here (we were pretty stuffed from our Chicago food-filled extravaganza), the menu of shareable small plates certainly looks tempting (they even have a vegan raspberry champagne truffle on the menu!). The hour-long magic show features an opening act and a headliner and strikes the perfect balance of funny, mysterious, and spectacular. If you really want an up-close and personal experience, you can purchase upgraded tickets to the 654 Club, an intimate theater with only about forty seats, where you can try to figure out the headliners’ tricks from your seat just a few feet away.

Tickets to the main theater start at $35, which is totally reasonable for such a unique experience where you easily will spend a couple of hours being awed and amazed. Make sure to buy tickets in advance, though; when my husband, Justin, and I went, Friday and Saturday night shows were sold out for a month in advance. If tickets are sold out when you’re in town, though, not to worry- entry into the Performance Bar is free and given the Willy Wonka-esuqe laundromat entry and bartenders’ tricks, is certainly worth a stop in its own right.  

Having went on a seemingly endless parade of online dates prior to meeting Justin, I consider myself somewhat of a online dating expert and can officially certify the Chicago Magic Lounge as the best date night spot out there. Good drinks, mood lighting, and a freaking magician to break up any potentially awkward conversations? Yes, please.

Strike a Pose 1,030 Feet in the Air

875 N Michigan Ave, Chicago, IL 60611

Saturdays at 9 am

This activity would be perfect on one of those super blustery wintery days where your face hurts from simply stepping outside (I’m looking at you, December through February). Every Saturday at 9 am, 360 Sky Yoga offers an hour long yoga class, led by a roster of rotating yoga instructors, from the comfort of the 94th floor of the John Hancock Tower. For a mere $15 (which is notably cheaper than going up to the observation deck itself), this is a downright bargain (in my experience, most drop in yoga classes, in boring, old studios, are about $20).When Justin and I went, the class was a kundalini-based practice, but I believe vinyasa classes are more common. During our visit, clouds were obstructing the certainly dazzling views of Chicago’s urban sprawl and Lake Michigan below, but even striking a pose in the clouds is pretty cool, no?

If yoga isn’t your thing, a bunch of other fun (and affordable) activities are offered through the observation deck- check out the free trivia night every Friday (running March through June and September through October) or happy hour every Thursday from 6-9 PM, with Revolution Brewing beer specials and bar games. If giant jenga at 1,030 feet doesn’t sound like your idea of a good Thursday night, we’re not going to be friends.

Hit a Burlesque Show

Chicago is famous for its theater and comedy scene, so it should come as no surprise that Chicago is bursting at the seams with great burlesque any Friday or Saturday night. While the word “burlesque” typically conjures images of feather boas and nipple tassles, a burlesque show is typically much more than that- I’ve seen everything from mind readers to banjoists and sword swallowers as part of the acts.

On this particular visit, Justin and I went to the Big Sexy Show at The Comedy Bar, which featured a wide variety of acts, including (wait for it….) FOOT JUGGLING. Better yet, The Comedy Bar is situated atop Gino’s East Brewing Company, so you can sip on Chicago-brewed beers whilst watching gorgeous pin-ups suggestively remove their elbow-length gloves.

The Big Sexy Show felt a little bit more like a comedy show than a “typical” performance, so it would be the perfect introduction for a burlesque virgin. If you’re looking for a more dance-centric show, Kiss Kiss Cabaret at the Uptown Underground, every Friday and Saturday night, features lovely ladies dancing with wonderfully kitschy outfits (at a show around Christmas time, one of the performers literally jumped from table to table, while shooting marshmallow-topped arrows out of a bow, perfectly choreographed to “It’s a Marshmallow World” by Darlene Love). If you really want to experience burlesque, you can even take a class with Vaudezilla Studios- we did this for my bachelorette party (don’t worry, no clothing items were removed) and had a total blast! Whether you’re just a spectator or learning the moves yourself, the burlesque scene is not to be missed when you’re visiting the Windy City.

Feel Lei’d Back at a Tiki Bar

3154 W Diversey Ave, Chicago, IL 60647

Monday through Friday 5 PM-2 AM; Saturday 4 PM-3 PM; Sunday 4 PM-2 AM

If you love kitsch and cocktails as much as I do, you will be smitten with the perfect amalgamation of these two concepts at Lost Lake, a tiki bar tucked away in the Logan Square neighborhood. From the instant you step foot into the bar, you will immediately be transported to a tropical paradise, from the walls festooned with palm fronds to the bartender with a vibrant orchid tucked behind her ear. While some tiki bars can be a bit over the top with their decor,  Lost Lake has seamlessly combined colorful, atomic Hawaiian accents with more modern design touches to create an effortlessly cool environment, making this an awesome date night spot or place to pregame with friends

Snag a seat by the bar to watch the bartenders whip together their dangerously drinkable concoctions, complete with wacky and wonderful garnishes, like dolphins crafted out of bananas. While many tiki bars only feature rum-based drinks, Lost Lake has geniusly engineered cocktails that contain the likes of such spirits as absinthe, gin, and sherry and have also managed to craft tiki drinks that are not cloyingly sweet. This bar gets crowded with hip, young professionals, so grab a spot (and a cocktail) early in the evening to people watch some of Chicago’s best and brightest.

Hopefully, these activities will keep you nice and dry in a climate-controlled environment, even when Chicago’s climate is anything but. Do you have any tips or recommendations of unique spots to hit in the Windy City, when the weather isn’t cooperating? Let me know in the comments below!