Reporter Shares Regrets from First Trip to Chicago

I spent 48 hours in Chicago for the first time and left with 4 regrets

A Business Insider reporter has some regrets about her first trip to Chicago. Joey Hadden/Business Insider I visited Chicago for the first time in February 2026 and spent two days there. Booking a winter trip was a mistake, and so was spending so much time outdoors. I also regret booking multiple hotels and exploring too many neighborhoods. When I decided to take the longest train ride in the US from Chicago to Emeryville, California, on Amtrak's California Zephyr, I thought I might as well...