Chicago's Coolest and Most Romantic Date Ideas
There’s no way around it, Chicago: Winter is coming. To deal with this most unfortunate turn of events, you’ve got several options. 1) Flee the state and couch surf all winter in your buddy’s shitty LA studio apartment. 2) Hide in your own apartment all winter ordering takeout and cleaning services, in that order. Or 3) Make the best of it, like an adult.
When it comes to option No. 3, there’s no better way to deal with cold weather season in Chicago than to have someone there to deal with it beside you. But you’re gonna have to go on at least a few dates before that happens. Luckily, we’ve made the process -- whether that's a first date or a fiftieth -- as painless as possible with these Chicago cold-weather date ideas. Feel free to take credit for all of them.
Engage in some good old-fashioned snow sports
For a winter date your parents would be proud of, take your significant other to a local ice skating rink like Millennium Park’s traditional McCormick Tribune Ice Rink, where you can chase flakes while holding hands like something out of the movie Serendipity. Additional ice skating options include the top-notch ice skating ribbon at Maggie Daley Park and the rink outside Wrigley Field at Winterland at Gallagher Way. You can also tackle the 33-foot sledding hill outside Soldier Field (where the city even creates fake snow in the absence of the real stuff), or try your hand at snowshoeing Northerly Island during the Chicago Park District-hosted Polar Adventure Days. Wholesome, right?
Two words: wine igloo
They may be called “river domes” these days, but they’ll always be wine igloos to us. Whatever you call them, make sure to seek shelter from the cold this winter at City Winery’s Riverwalk location where you can eat and drink in an intimate, climate-controlled igloo/dome by the river. Doesn’t get much more romantic than that, now does it? Note: Reservations required.
Seek shelter from the elements at a fireplace bar
Fireplace bars are to Chicago winter as outdoor patios are to Chicago summer. In other words, they’re essential. From the hip Scofflaw to the wintry knight’s roundtable that is Moody’s Pub, there’s no shortage of options to spark a winter flame over a cocktail or two in one of the coldest winter cities in America. Read our full rundown of the best fireplace bars in Chicago here.
Drink on a rooftop bar
It’s never a bad idea to get a drink with a date at a Chicago rooftop bar, no matter the season. While it’s gonna cost you a bit more than your corner dive, you’ll feel fancy, the views are incredible, and you’ll look an extra point or two better in the eyes of your companion just by showing up. Get a sampling of the best rooftop bars in Chicago here.
Engage in some silly sports
Get close and personal with the old man winter sport of kings at the Chicago Curling Club (yes, this exists -- but it's more expensive for serious lessons). You can also shoot bows and arrows in Humboldt Park at Archery Bow Range Chicago or chuck axes at the wall at joints like Bad Axe. (These spots aren't too pricey and tend to have cheaper rates for groups and other options too.) There’s also shuffleboard/drinking at the hip Royal Palms, and the beer garden ice curling rink at Kaiser Tiger is tough to beat.
Take in some live comedy
Second City is, of course, the granddaddy of comedy-themed date nights, but good times can also be had for fewer dollars (and fewer people from Iowa) at indie comedy venues like the Cornservatory or regular stand-up nights like Timothy O’Toole’s “Comedians You Should Know” (see full list here). Fortunately, comedy shows tend to be pretty cheap dates.
Take in a night of theater
The entire city of Chicago has a ton of excellent theater. If you want to keep it in the neighborhoods, the Belmont Theater District in Lakeview is actually the largest in the city if you count by theaters. But is there anything more romantic than the 100-year-old theaters in the Loop Theater District, like the CIBC for you high-roller Hamilton lovers or the Auditorium Theatre for fans of live music and dance? We think not.
Keep it on the lowdown at a secret bar
Show off how cool you are with your in-depth knowledge of Chicago’s secret bars. Since knowing that the mural on Damen in Wicker Park opens up to Violet Hour is no longer considered insider information, Booze Box is a sexy bet, The Office is uber-swank, and East Room is not technically secret but does lack proper signage.
Nerd out at bar trivia
If your ideal date involves demonstrating what a stable genius you are, show off your deep base of useless knowledge at one of the many bar trivia nights around town. The Globe Pub is the granddaddy on the scene, Reggie’s is a great Monday night spot for sports and music trivia, and Simone’s is a standout choice for Q&A trivia Tuesday nights.
Go for dinner and a movie (duh)
The stylish Logan Theatre or Music Box Theatre is always a solid date choice, but becomes even better when you can enjoy an ice-cold pre- or post-movie cocktail at the bar inside..If you’re looking to get a bit rowdier, Brew & View is never a bad idea, while a fancy dine-in movie theater like AMC Dine-In Block 37 is the ultimate low-pressure, two birds/one stone lazy afternoon out.
Live it up at a tiki bar
There is perhaps no easier winter date than at one of Chicago's fine tiki bars: immediately fun and tropical, the only way you can screw this up is to start talking politics. Three Dots and a Dash and Lost Lake are among the most famous in the city, but alarmingly fun times can also be had outside city limits at popular suburban hangs like Hala Kahiki and Chef Shangri-La.
Get smart at a boozy bookstore
A bookstore may not sound like the most exciting date in the world, but places like Lincoln Park’s Kibbitznest are tailor-made for winter. With a front room stacked with newspapers and magazines, a bar stocked with everything from Chicago dogs to Irish coffee, and a back game room, a quick stop in from the cold here can quickly turn into three hours gone by in a flash.
Road trip to New Glarus or Lake Geneva
Just because it’s winter doesn’t mean you can’t road trip. Enjoy the great open highway with the tunes cranked up and show your date a change of scenery. Hit up Lake Geneva for some gorgeous (indoor) waterfront drinking during the much more laid-back off season, New Glarus to enjoy “America’s Little Switzerland” (and lots of yummy beer), or any of a slew of other options.
Scale cliffs at an indoor rock climbing facility
Not only is a place like Brooklyn Boulders the ideal location to scale fake rocks when you can't get out to the real thing, it also cultivates a fun scene with a regular slate of events including pizza parties, movie nights, yoga, and more. A full day pass is just $25.
Join the circus at Aloft Loft
One of the most awesomely weird spaces in the city, Aloft Loft is located in a 110-year-old Logan Square church and offers a variety of circus performances and classes in everything from aerial arts and trapeze to contortion and clowning. If your relationship can survive a clown class, it can survive anything. Check the schedule for pricing and classes.
Feel the heat at Garfield Park Conservatory
The Garfield Park Conservatory, which is brimming with lush plant life year-round, is a sight for sore eyes after a winter of staring at gray skies and barren concrete. Admission is totally free, but leaving a donation at the door can't hurt your chances with your date.
It doesn’t get much more Chicago than turtle racing at Big Joe’s. But remember, there are rules. If your date is a natural at turtle racing, this can only mean good things are on the horizon. Trust.
Dance with Lady Luck at an area casino
Chicago may not be known as a gambling mecca per se, but the city is surrounded by a variety of casinos that can make for a fun alternative to the standard dinner-and-a-movie routine. Hit up suburban casinos like Rivers Casino, Harrah’s, and Grand Victoria, or ride the shuttle to places like Horseshoe Hammond and try to get lucky in more ways than one. Some free advice: Don't spring this one on a first date unless you know you're both high rollers.
Get kitty with it by petting cats
As the old saying goes, the couple that pets cats together stays together. For a super-fun time with some cute little furballs, check out The Catcade in Lakeview or Windy Kitty Cat Cafe in Wicker Park. In either location, you and your date can hang out in comfy chairs and get to know each other, or just “ooh” and “aah” over the adorable (and adoptable) cats all around you. Plus, you get to show off your gentle side. Which is nice.
Attack the pins at a bowling alley
In the wise words of that dashing Casanova Walter Sobchak: “Fuck it, Dude. Let’s go bowling.” This indoor sport where you're encouraged to drink is one of the great fun equalizers we have on this planet. Luckily, Chicago is brimming with lively bowling options like Diversey River Bowl and Southport Lanes. Or, if you prefer your bowling with more weird bumper cars, a winter date to Whirlyball is clearly calling your name.
Unleash your inner Picasso over a bottle of wine
Painting parties paired with wine are the name of the game at uber date-friendly spots like Bottle & Bottega. If you can’t seal the deal after this date, something must have gone seriously wrong (let’s hope it wasn’t your art).
Learn the art of the tease at a burlesque show
Chicago’s burlesque bona fides are not to be questioned, and you can sex up your night out with a visit to one of the city’s many burlesque stomping grounds like Untitled or The Drifter. Stop by the store to pick up a few tassels and feathers if you want to try and re-create the experience at home.
See a concert in a living room
It’s always great to see a concert at a major venue like the Riv or Aragon, but if you’re looking to save a few shekels while still partaking in the live music experience, there’s no shortage of great bars with live shows in Chicago. And as much as we love Beat Kitchen and the California Clipper, we simply cannot end this paragraph without recommending The Hideout. Or if you’d rather see live music in the comfort of your own living room, check out Sofar Sounds.
The Lincoln Park Zoo makes for a great first date, and not just because it’s free (but also, that’s pretty cool). Much like a festival, the zoo itself provides plenty of conversation starters, so you probably won’t have to worry about awkward silence. Plus, it’s in Lincoln Park, which is a great neighborhood for grabbing lunch or dinner after you’re done staring at wild animals together.
Learn about our tallest and most impressive buildings
Any kind of Downtown tours have the reputation that they’re for tourists, but that’s a shame. There’s plenty for Chicagoans to learn about their city, and an architecture tour makes for an awesome date. (Choose either a walking tour or hop on a bus tour if you get cold.) And secondly, Chicago’s architecture is awesome, period. This is the perfect option if you want to impress your date with how cultured you are, but don’t want to sit in a dark theater or walk through a museum for two hours.
Plot your getaway from an escape room
When on a date, it’s always good to have an escape plan in case things go sideways. But instead of faking an emergency, book a trip to a local escape room like Room X Escape where you can choose your own adventure like trying to escape an old house with secret treasure before the creepy pirate returns for his stash.
Experience a night at the museum
Every third Thursday of the month, Adler After Dark -- one of our best museums -- welcomes in couples for themed events that include live entertainment, museum access, unlimited sky shows, and some of the best skyline views in the city. General admission is just $19 a person.
Head underground to navigate the city
The Chicago Pedway was created for the very purpose of navigating the city to lessen the impact of the cold and snow of winter, so it’s the perfect place to explore this season with an adventurous date. You can also hop on the L and scour the city for burgers, if that’s your thing (hint: it’s your thing).
Get really weird around the city
If you’re looking to get weird in Chicago, a date to an off-the-beaten-path location like the International Museum of Surgical Science is a pretty good bet. You can also check out a leather museum with its own dungeon, screening room, and leather bar. Fortunately, we have a guide to weird things that will make this an easy search. Our quirks bring us closer, after all.
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