I have just come back from a holiday in Chicago. I have been there very many times, but always enjoy going again and always find new and rather surprising things to do.
It is a very special place. If you love your architecture then you will find plenty to enjoy. The boat trips down the river were really busy, and are worth doing.
It’s a great place for walking, and the food can be wonderful. Yes, sure there are the rubbish places, but there are some truly wonderful places, especially if you are a meat eater.
What sets the city apart are the people, who are genuinely friendly and polite. Given its size, it is a clean city too.
Definitely worth a visit, if you can. Don’t dismiss it as just another big city, because it isn’t. There’s a chance to see some fine theatre at reasonable prices, and the Navy Pier is one of the biggest attractions in the whole country.