Dating in Chicago is so complicated… but worth every moment with you.

Let’s unlock all the sweet things to do together in the Windy City 🔓 Stroll through Millennium Park and take that classic photo with The Bean 🤳 Pose under the “You Are Beautiful” sign in Chinatown 🥰 Walk under pink cherry blossoms near the Museum of Science and Industry 🌸 Shop at Mitsuwa and fill your cart with snacks, sushi, and Japanese cosmetics 🛒🍣 Watch the sunset at Openlands Lakeshore Preserve — the “trees in the clouds” view is magical 🌅 Escape to a Getaway cabin — just you, the stars, and the crackling campfire 🔥🎶 Ride roller coasters at Six Flags and pretend you’re not screaming inside 🎢😆 Explore Farmers Markets for fresh tomatoes and blueberries still glistening with dew 🍅🫐 Step onto the Willis Tower Skydeck — whoever gets weak knees first owes the other a treat 🐶 Get lost together at the Art Institute of Chicago 🖼️❤️ Take a spontaneous road trip — Route 66 or Michigan’s tulip fields 🚗🌷 See the Buckingham Fountain — the world’s most Rococo “wedding cake” fountain 💒 Walk along the Chicago Riverwalk during the Art on theMART light show 🌃 Cheer at a Bulls game and hope the Kiss Cam picks you 🏀💋 Visit Shedd Aquarium — the rolling otters remind me of you in bed 🦦🛏️ Sip warm mulled wine at the Christkindlmarket and collect this year’s mug ☕🎄 Cruise down Lake Shore Drive with the lake on one side and you on the other 🚗💨 Stuff yourselves at all-you-can-eat BBQ (we never get our money’s worth 😂) Chase fall colors in Northern Michigan — Porcupine Mountains and Pictured Rocks 🍁🏞️ Adopt a round-eyed orange cat and spoil it lazy and fat 🐱🍊 Pick strawberries, blueberries, and cherries at a farm — then eat nothing but berries for a week 🍓🍒 Wait in line at Green Street Smoked BBQ for fall-off-the-bone ribs 😋 Attend graduation — one on stage, the other clapping proudly in the crowd 🎓👏 Watch the sunset from 360 Chicago — your face glows so cute in the golden light 🌇🧡 May your life in Chicago be super, super sweet! 🍬 #Chicago #ChicagoLove #DatingInChicago #TravelCouples #WindyCityRomance #USATravel