AMTRAK Chicago Trip 2026

NOTE: This trip is not planned for Dec. 31. This just keeps the event open while we nail down a date. We've been talking about this trip for awhile, too, but maybe not as long as the NOLA trip. Time to make it a reality. We are still in the planning stage, though, getting all the details, and your answers will help us set this up for the best experience for everyone, so please chime in, and please answer ALL the questions in the signup phase. I recommend that you read through the entire description BEFORE you RSVP, please. In order to maximize our time while minimizing the amount of vacation days folks will have to take off work, I recommend that we: Leave Friday evening (depart: 10:40p FRI - arrive: 9:15a SAT) Return Tuesday evening (depart: 8:05p TUE - arrive: 6:27a WED) This gives us basically 4 full days in Chicago. Best time of year: May and September to October are great times to enjoy less crowded museums. Chicago has two shoulder seasons — in late spring and early fall — when the city is either shaking off the winter chill or preparing to head into it. Both are excellent times to visit. Suggested itinerary: https://gocity.com/en/chicago/blog/chicago-itinerary?gad_source=1&gclid=Cj0KCQiAsvWrBhC0ARIsAO4E6f98ZCOgOqvWITVBt5fi4NmBiUTP6u0Zu8i-XF_Z0m_hWWWwzslFtXQaAthuEALw_wcB. Please read the 3 Days in Chicago for First Timers and let us know which things on there interest you. Also, feel free to let us know if there is something you'd like to do that is not on that list. Tickets & Lodging: Everyone will be responsible for their own AMTRAK ticket and lodging, but I'd like to recommend: AMTRAK coach: Price (roundtrip): $192 (2 bags free) flex (which allows you to cancel or change dates) Lodging @ Airbnb (which is usually much cheaper per…