Meet your guide and group at the Amtrak Station, 433 W St. Paul Avenue, in Milwaukee at 7 a.m. to catch your departing train. Enjoy the scenery on the way there, then disembark to start your day of adventure.
Begin with a visit to Skydeck Chicago, including Fat Pass access, where you can take in views of up to 50 miles (80 km) and learn about the history of Chicago through the observation deck's touch screen displays. If you're feeling brave, step out on to The Ledge, a glass floor balcony that allows you to look straight down.
Spend the rest of the day exploring area attractions such as Water Tower Place, 36 Chicago, Navy Pier, the Shedd Aquarium, Millennium Park, the Art Institute, and finish up with a stop at the Hard Rock Cafe before returning to Milwaukee via train.