If you’re going to Chicago for the “Hamilton” exhibition, or just for a whirlwind weekend in the Windy City, planning and prioritizing are your best friends. On a spring jaunt with my 22-year-old niece, a Chicago first-timer, I picked up some tips for making the most of a short stay.
• Try to leave the car at home. Chicago is an easy drive, but parking at hotels in the heart of the city, where you’ll want to be, is uber expensive. And speaking of Uber, or Lyft, ride-sharing services take you everywhere cheaply and quickly.
• Get an overview, especially if you haven’t, with Big Bus ($41.40; kids $27) or one of the other tours that circle the city, narrating along the way. The tours let you hop on and off at attractions — but really, don’t. The drop off and pickup points are not at the door, and catching the bus again is harder than the drivers suggest. We wished we’d ridden all the way around, then returned to the attractions we liked.
• If you want to see everything, you can’t do better than CityPass ($108; kids $89), a booklet of tickets that also includes VIP entry at many popular attractions. But do the math: If you’ve set your sights on just two or three spots, you might do better paying individual admission. Some of the places we enjoyed most are free, including Millennium Park, home of the entrancing “Bean” sculpture, and Navy Pier.
• Chicago’s Art Institute is spectacular, and a must-see. It’s also quirky in that the multiple wings don’t connect with one another except on the second floor. To make the most of your time, and save your feet, look up the locations of the pieces you want to see most and plan accordingly. My niece enjoyed the enormous collection of miniatures on the first floor, and I couldn’t get enough of the Impressionism galleries on the second level, even finding a new favorite, Gustave Caillebotte’s wall-size “Paris Street: Rainy Day.” (You can buy it as an umbrella in the gift shop. Don’t miss the gift shop.)
• The two attractions that take you high up, letting you look out over the city while standing on glass, are a favorite spot for Instagram selfies. We rode escalator after escalator, wound through hallways and zoomed up in an elevator to the top of the Willis (formerly Sears) Tower, and were underwhelmed. The view isn’t spectacular, you’re closed in, and the glass floor actually isn’t scary, even though one did crack recently. We didn’t add 360 Chicago to our schedule, but we heard it’s best a night, with the city lights below.
• Go on, have deep dish pizza and hot dogs with that fluorescent green relish. It wouldn’t be a Chicago trip without them. Navy Pier, a haven for souvenir shoppers, especially on a rainy day, is packed with snacking opportunities.
• Tailor your trip to your own likes via ChooseChicago.com, which offers a free visitors guide.