Air travel mask mandates just came down. Take it as a sign you’re supposed to go. ?It's on my bucket list to attend someday. It's not an inexpensive proposition to travel from Texas. I don't have the funds, but if I ever do... I'd just like to walk around and experience everything I can.
I imagine it's nice.monty55, in more normal times, there is or was an annual pipe show much closer to you, maybe in Las Vagas or California. The shows tend to be outside the cities that bear their names. The Chicago show is at a town well outside the City of Chicago, and the New York show is in New Jersey (when they're held, of course).
This brings the cost of the venue, the hotel or resort, down quite a bit, within the reach of a recreational pipe smoking clientele. If you then want to combine your trip to include the big metropolis, you have to make all those arrangements independently.
Chicago is an amazing city to visit. I grew up near there, just outside city limits, and commuted there to school, and started visiting the downtown alone in high school, but it never fails to impress me. The boat ride down the Chicago River gives a perfect introduction, and the Art Institute and nearby Millennial Park are not to be missed. Etc.