Chicago’s Coolest and Most Romantic Date Ideas

© Chicago Architecture Center

Let’s face it: 2020 has not made dating easy. If you’ve managed to thus far weather the ups and downs of the almighty quar with your relationship intact, may the gods bless you eternally. And if you’re single and trying like hell to mingle at a safe and sanitary distance these days, may they bless you doubly. It’s rough out there and with winter slowly slithering closer, it’s only getting rougher. That’s why we put together this ingenious list of Chicago-centric, quarantine-approved date ideas to keep your little love flame a-burning for many, many months to come. It’s time to grab your sexiest face mask and get on out there.




© Lakeshore Drive-In

Cuddle up at a drive-in movie or live event

All outdoor everything is the name of the game this year, a mantra that certainly extends to entertainment. Chicagoland movie buffs and their beloveds flock to pop-up screeners in Pilsen, Lincoln Yards, Bridgeview, and Hoffman Estates while throwback-seekers make a beeline to the nearby sticks for a real-deal retro experience at Golden Age Cinemas in McHenry or Route 34 Drive-In Theatre in Earlville.

Unsurprisingly, al fresco viewing has also breathed new life into live theater, music, and comedy. Lakeshore Drive-in brings a diverse lineup of DJs, funk bands, and other must-sees to Northerly Island, the McHenry Outdoor Theatre is holding it down with Iliza Shlesinger’s knee-slapping tailgate tour among other noteworthy acts, and you won’t want to miss Seatgeek Stadium’s unprecedented Mock Stadium Tour, a socially distanced hard-rocking bash featuring Def Leppard, Mötley Crüe, Poison, and Joan Jett tribute bands.




© On Tour Brewing Co.

Embark on a DIY brewery crawl

With so many great craft breweries clustered around the city, organizing a bicycle- or foot-powered suds crawl for two is always a failsafe date idea. What’s more, plenty of taprooms have expanded into beer gardens, breezy patios, and other sidewalk accomodations for pandemic-friendly sipping. Just pick a neighborhood (pro tip: Milwaukee Avenue from the Near Westside to Logan Square is a fantastic place to start) and hit the streets, lapping up as much sweet, sweet Chicago-brewed suds as you can.

Soak up the scenery on a seasonally inspired day trip

Have car, will travel. Pack your best fall flannel, build a killer playlist, and direct your GPS to the corner of nature and beauty, aka one of the many idyllic Midwestern towns bursting at the seams with technicolor foliage this time of year. Lake Geneva, with its wide open shoreline, panoramic vistas, and friendly downtown, makes for an excellent daylong destination while the picturesque village of Galena is close enough (and charming enough) for revitalizing afternoon escape. A little extra time on your hands? Go big and make an entire weekend out of it.

Day drink on a sunny rooftop bar 

If this hellscape of a year has had any silver linings, it’s undoubtedly a newfound and widespread incentive to do our drinking outdoors. Make the most of it with some swanky open-air sipping set to a sparkling skyline backdrop at one of these towering watering holes. You have to admit that’s a real win-win in a world where even the smallest win is huge.

Pick a peck with your partner

Think of a more romantic outing than autumnal apple-picking? Yeah, neither can we. Grab a basket and prepare to stroll arm-in-arm through rows of neatly planted apple trees as you search for the juiciest, crunchiest, most satisfying fall fruit the midwest has to offer. Later, challenge your boo to a pie bake-off — or just stock up on velvety soft cider doughnuts from the farm — for the ultimate sweet dream finale.




© The Forge: Lemont Quarries

Conquer your fears at the country’s largest aerial adventure course

Buckle up and start your engines, kids, because this date is not for the faint of heart. Thrill-seeking lovebirds can spend the day one-upping each other at The Forge: Lemont Quarries, a massive 300-acre adventure park complete with soaring ziplines, daredevil ropes courses, paddlesports, endless hiking and mountain biking trails, laser tag, and so much more. At the end of the day, don’t forget to stop into The Foundry, a sprawling beer garden and snack bar, to toast your collective accomplishments and rest your weary bones.

Hone your teamwork skills in a private escape room

Put your relationship to the test by booking your very own date night-worthy escape room experience at Fox in a Box. A web of thoughtfully appointed scenarios awaits, imbued with enough twists and turns to get your blood pumping and your brain ticking. And don’t worry about wasting precious time worrying about your health — each and every space is sanitized to perfection between games.




© Garfield Park Conservatory

Get your floral fix at the Garfield Park Conservatory

Garfield Park Conservatory is hands-down one of the Westside’s most beautiful best kept secrets. Whisk your boo out of the grey skied city and into the inviting warmth of the tropics while you let your eyes feast upon thousands of exotic plants of every make and model. The best part? It’s all free, just make sure to call ahead and secure a timed entrance slot to keep things nice and distanced.

Watch ‘da bears play at the Lincoln Park Zoo

Speaking of free, did you know that our fair city is home to one of the country’s only completely free zoos? You won’t need to shell out a single penny to check up on your favorite wild animals, whether you favor swinging monkeys, slow and steady rhinos, or something in between. A bargain that good is all the reason you need to treat yourself (and your mate) to a refreshing post-exhibit craft brew at the ever-serene Patio at Cafe Brauer.

Bask in glow of brilliant skyscrapers

Even died-in-the-wool Chicagoans can learn a thing or two aboard one of the Chicago Architecture Center’s stellar urban design tours. Traverse the city by boat, bus, or foot and see your hometown from a whole new perspective thanks to brilliant guides, masterful routes, and the awe-inspiring history behind the Second City’s wonderous built environment. The center has gone to pains to make sure each tour takes all the necessary safety precautions so mask up, pack some hand sanitizer, and settle in for a round of good old-fashioned schooling.

Dine beneath the stars at a romantic outdoor restaurant

Staying socially distanced doesn’t mean having to sacrifice the pleasures of fine dining. Impress your special someone by snagging an appropriately spaced open-air table at Chicago date night institutions like River North’s stalwart Bavette’s Bar & Boeuf or hipster newcomer Chef’s Special Cocktail Bar. Thinking about throwing a known aphrodisiac into the mix? We’ve got all your Chitown oyster bar needs covered.




© Kayak Chicago

Paddle around town with Kayak Chicago

Stick with the nautical theme and descend upon the Chicago River with this enterprising kayak rental company. After a quick instructional demo, you and your first mate will be equipped to cruise the city’s vast waterways to your heart’s content or, alternatively, hop on a guided tour for an expert lay of the land (er, water). The City Lights evening jaunt is especially fit for lovers — you can even attempt to hold paddles as you float amid the glittering streets.

Show off your mixology skills with a take-home cocktail kit

If COVID’s wrath has put the kibosh on your favorite date night drinkery, you’ll be stoked to learn that a slew of award-winning local cocktail joints have been lovingly boxing up their boozy splendors just for you. We’re talking big names like the Aviary, Violet Hour, 3 Dots and a Dash, and more, all exquisitely prepared and portioned for at-home consumption. So roll up those sleeves, don your fanciest suspenders, and get ready to transform your humble living room into Chicago’s hottest club.  Sign up here for our daily Chicago email and be the first to get all the food/drink/fun in town.

Meredith Heil is a contributor for Thrillist.