Find a spot to snuggle amid 2 acres of tropical flora under glass at the free Garfield Park Conservatory. (There are 10 acres of outdoor gardens to explore, too.) If your heart’s set on a Broadway show, two Hot Tix locations sell half-price tickets for day-of performances. (Planning ahead? Check AAA.com for member-exclusive discounts.) For an insider’s guide to the city, go on a free Chicago Greeter tour led by a local; you just need to book 10 business days in advance. And don’t leave without snapping a photo together at the Cloud Gate sculpture—aka, The Bean—in Millennium Park.
AAA inspector picks: Spacca Napoli serves up authentic Italian food—including amazing Neapolitan-style pizza. Stay the night at ACME Hotel Company, near Navy Pier. Guest rooms feature high-tech extras like streaming smart TVs and Amazon Echo speakers.
Go on a shopping spree together along the Magnificent Mile—a stretch of Michigan Avenue packed with high-end boutiques, upscale department stores and even an eight-story mall. Give your feet a break and take the elevator to the 95th floor of the former John Hancock Building for cocktails with a view at the Signature Room at the 95th. For the ultimate in relaxation, sink into the thermal pools at Aire Ancient Baths, housed in a restored factory that dates to 1902. The Grand Indulgence Experience for Two includes a soak in the baths (hot, warm and cold), a full-body massage, foot massage and lavender body scrub for $700-plus.
AAA inspector picks: Introduce yourself to molecular gastronomy at Alinea, where the 10- to 12-course dinner isn’t just a meal but an experience designed to impact all five senses. (You’ll need to make online reservations before you go.) For an overnight stay, the Viceroy Chicago wows with floor-to-ceiling windows in every room.