Chicago’s Coolest and Most Romantic Fall Date Ideas

Cuffing season is right around the corner…

Let’s face it: Dating during a pandemic isn’t exactly a walk in the park. But now that we can once again walk in the park—amidst some epic fall foliage, we might add—we’re more eager than ever to embrace it.

As it turns out, Chicago is stocked with romantic activities right now, from artwork and orchard outings to staycations and service opps. Whether you’re planning date one or 1001, here are a handful of ways to fall in love this fall—with your S.O. and our fine city alike.

The Art of Banksy
The Art of Banksy

Head to a museum pop-up (while they last)

Abounding in opportunities for discovery and here for just a moment in time, the museum pop-up is understandably all the rage right now. And the fact that these labyrinths are often built on a “choose-your-own-adventure” premise provides a novel way to learn more about your plus one, too. Banksy enthusiasts can now encounter the elusive UK-based artist with The Art of Banksy, the largest collection of works under one roof (including “Girl and Balloon” and “Flower Thrower”). Shine bright at Neon and Light Museum, a vibrant assemblage of illuminated works from artists around the globe. And Immersive Van Gogh is still going strong, inviting you and yours to explore a dazzling projected art display of the Dutch artist’s work across the walls (and floors and ceilings) of five ornate rooms.

Edwards Apple Orchard
Edwards Apple Orchard

There’s perhaps no better way to celebrate fall than with a visit to a nearby orchard—hot cider (and cider doughnut) in hand. County Line is ripe with activities and attractions, from u-pick experiences and corn mazes to live music and campfires. For less work and equal perks, let the pros do the picking—such is the case at Rubber Ducky Farms, where a fleet of barrels brim with varieties ranging from McIntosh and Gala to Honeycrisp and Jonagold (not to mention an ace example of those aforementioned doughnuts). And If you’re sans wheels or would otherwise rather stay within city limits, head to Jack’s Pumpkin Pop-Up, where carnival games, axe throwing, and Chicago’s largest corn maze await.

PAWS Chicago
PAWS Chicago

There’s nothing more attractive in our book than a benevolent heart, and our city offers plenty of ways to flaunt such a trait. Evaluate your beau’s lit and kid skills alike with some tutoring sessions at 826 Chicago, a nonprofit offering creative writing and publishing opportunities to Chicago youth. See if you’re pet-compatible by spending some onsite animal QT at any of the city’s animal shelters (including PAWS and The Anti-Cruelty Society), which are often in need of eligible volunteers. And if impromptu aid is more your thing, visit ChicagoCares.org, where you and your boo can brose several one-off ways to serve.

Thalia Hall
Thalia Hall

Size up each others’ boogie skills at a concert

While last year was a bit of a bust, live music is making a fierce comeback at all of our favorite local venues—and the fall concert circuit is looking as strong as ever. Head to Thalia Hall for a night with The Lone Bellow, a Brooklyn-based trio whose energetic folk-rock and engaging stage presence guarantee an evening of clapping and toe-tapping. Over at House of Blues, make way for four-time Grammy-nominees Black Pumas, whose hits “Colors” and “Fire” made serious chart-topping waves this year. And if classical or jazz is more your frequency, book it to one of Fever’s Candlelit Concerts, which span everything from Mozart to Miles Davis.

Get vaccinated

There are now myriad sites across Chicagoland offering COVID-19 vaccines—so why not make a weekend of it? We’re just saying. Could be cute. And if your honey happens to faint at the sight of the needle, at least you’ll be there to catch them.

Pendry Chicago
Pendry Chicago

Splurge on a luxury staycation

When a full-on excursion feels too costly—or like too much of a commitment—nothing sets the mood like a properly staged staycation. Enter Nobu Hotel—the luxe property brings with it 115 rooms, each one packing high-end perks (think exclusive Nobu beds, a private bar, and walk-in showers). And then, of course, there’s the food. Visit the signature Nobu restaurant on the ground floor for show-stopping nigiri and sashimi, and for al fresco dining, make a beeline for the Rooftop at Nobu, where house favorites like Tuna Tacos, Rock Shrimp Tempura, and Black Miso Cod are front and center.

Within the Loop, spring for a stay at the brand-new Pendry Hotel, housed in the historic and architecturally stunning Carbide & Carbon Building. Expect upscale details around every bend—and ample choices when it comes to F&B. Head to the rooftop for sushi rolls and rose at Chateau Carbide, and at lobby-level, enjoy elevated brasserie fare from chef Donald Young at Venteux, followed by a high-caliber nightcap at Bar Pendry.

Sushi Boutique
Sushi Boutique

If you’re wining and dining these days, options abound. Impress your special someone by copping an outdoor table at Chicago date night newcomers like Sushi BoutiqueDear MargaretVerve Wine & Provisions, or the shiny new River North outpost of Bar Avec (complete with gargantuan G&Ts).

Don’t miss this city’s old reliables, either, each one boasting its own bonuses—a tasting menu steal in Bucktown (The Bristol), elevated pub fare in Pilsen (Dusek’s), vintage cocktails in the Loop (Milk Room), and swoon-worthy pastas or flavor-packed shareables in Logan Square (Daisies and Giant, respectively). Thinking about throwing a known aphrodisiac into the mix? We’ve got all your Chitown oyster bar needs covered right here.

The American Club Resort
The American Club Resort

Have car, will travel. Pack your s’mores kits and flannels, build an epic folk-fall playlist, and direct your GPS to the corner of nature and beauty for a seasonal escape to some of the mighty Midwest’s most charming towns. Wisconsin’s Lake Geneva, with its wide open shoreline, panoramic vistas, and friendly downtown makes for an excellent sojourn with posh sleeping quarters—namely at the historic, speakeasy-equipped Maxwell Mansion. Verdant hill-scapes from Otsego, Michigan to Illinois’ own picturesque Galena cater to mountain bikers yearning to burn trail. And over in Kohler, the illustrious American Club (and all of its A-grade amenities, from a world-class spa and championship golf courses to private cabins) is even more idyllic come autumn. Got a little extra cash on your hands? Go ahead and treat yourself to a top notch stay in one of these swanky Airbnbs.

Maplewood Brewery & Distillery
Maplewood Brewery & Distillery

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 and other sidewalk accommodations for sharing open-air pints. It’s all about the ambience! Just pick a neighborhood (pro tip: Milwaukee Avenue from the Near Westside to Logan Square is a fantastic place to start), strap on a mask, and hit the streets in search of sweet (or sour, or roasty, or bitter) Chicago-brewed suds.

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Nicole Schnitzler is a contributor for Thrillist.