Chicago is full of romantic spots, fun date activities, and unforgettable experiences for couples! Whether you're planning a cozy night out, a scenic adventure, or a unique date, this list has the best things to do in Chicago for couples—from breatht...
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5
Romantic Views & Skyline Moments
Romantic Dining & Cozy Cafes
Unique & Fun Date Ideas
Adventurous & Playful Date Ideas
Seasonal Date Ideas
Romantic Views & Skyline Moments
Ride up to the 94th floor for skyline views and try the TILT experience together. Sip cocktails at the rooftop bar afterward for a relaxed vibe.
360 CHICAGO Observation Deck: John Hancock Observatory
Take photos on the glass ledge 1,353 ft in the air. A bold, memorable moment for adventurous couples.
Skydeck Chicago - Willis Tower
Relax on the sand with unbeatable skyline views. Pack snacks and watch the sun dip behind the buildings.
North Avenue Beach | Chicago Park District
Take a romantic evening stroll by the water. Stop for wine or dessert at one of the cozy riverside cafés.
Chicago Riverwalk
Enjoy cocktails with a panoramic view of the river and skyline. Chic, upscale, and perfect for golden hour.
LondonHouse Chicago
Romantic Dining & Cozy Cafes
Fondue, candlelight, and live flamenco guitar = one of Chicago’s most romantic restaurants. Perfect for an intimate, old-school date.
Geja's Cafe - Fondue Restaurant in Chicago, IL
A moody, jazz-filled steakhouse with a speakeasy vibe. Date night goals.
Bavette's Bar & Boeuf | Chicago
A cozy, rustic coffee shop with matcha, espresso, and latte art. Great for a casual daytime date.
Sawada Coffee | Chicago
Chill, funky, and fun. Perfect for brunch dates with a twist!
Little Goat Diner | Chef Stephanie Izard | Southport, Lakeview Chicago
Unique & Fun Date Ideas
A speakeasy-style magic show where you enter through a laundromat. Mind-blowing, immersive, and unforgettable.
Chicago Magic Lounge | Magic Bar and Theater | Andersonville
Legendary jazz bar once frequented by Al Capone. Sip cocktails and sway to live jazz in a vintage setting.
Green Mill Jazz Cocktail Bar
Relax, laugh, and get creative side by side. Bonus: you get to keep your artwork!
BYOB Paint & Sip Art Class
Team up to solve puzzles and escape together. Great for bonding and bringing out your playful side.
Chicago's Original Escape Room Games · Escape Artistry
Laugh together with live improv comedy. Because couples that laugh together, last together.
Comedy Shows in Chicago - The Second City
Adventurous & Playful Date Ideas
Kayak along the Chicago River as the sun sets or fireworks go off. Major main-character energy.
Urban Kayaks | A Great Chicago River Tour & Lake Excursion
Cozy up while you rise above the city. Go at night for the most romantic skyline views.
Centennial Wheel | Navy Pier
Retro games + drinks = nostalgic and playful vibes. Challenge each other to Pac-Man or pinball!
Emporium Arcade Bar - Fulton Market
Classy yet casual spot for bowling, bocce, and bites. Perfect for when you want something active but chill.
Pinstripes | Bistro Bowling Bocce
Rent Divvy bikes and ride side-by-side along the lake. Pack a picnic for the perfect day date.
Lakefront Trail | Chicago Park District
Seasonal Date Ideas
Lace up your skates and glide beneath the city lights. Hold hands, even if you're wobbly.
Millennium Park Ice Skating
Escape into a tropical oasis and wander through lush gardens. A hidden gem for cozy, peaceful vibes.
Garfield Park Conservatory
Set up with snacks, a blanket, and your favorite playlist. Sunsets here hit different.
Montrose Beach | Chicago Park District
Perfect for fall time. Take a walk under golden leaves, then grab a cider nearby. It’s giving main character love story.
The Morton Arboretum
Watch a movie under the stars on a rooftop with headphones and cozy vibes. Blanket + popcorn = perfection.
Rooftop Cinema Club Fulton Market - Outdoor Movies in Chicago
