One in each season I did an Amtrak trip from Denver - Chicago (sleeper car). I am a masochist who loves train travel. I'll report on Amtrak later.
Anyway, I have been to most U.S. cities and grew up in the NY area,
I have to say that, especially in good weather Chicago is by far the best city to visit - in my opinion. IT surprises me how so few of the folks who I know have been there. I always hear: "I've been to the airport," or "I always wanted to go."
It's a terrific, walkable, and visually appealing place that I never get tired of.

I enjoyed my only visit to Chicago. We went to the Chicago Art Institute and saw "Evita" the musical. Plus, we ate some fantastic Greek food.

I've been. Chicago is a fabulous city. But the weather is most definitely not for me, as far as any consideration of possibly living there.

It's is indeed one of the best time of the year to visit Chicago, especially now during the holidays.

In case you haven't already seen it, here is my recent trip report:

First-Time Chicago, Oct 22 to 26 - Report

I visited Chicago last year for the first time. Very interesting city. Great lakefront for beaching and bicycling and plenty of interesting skyscrapers. I won't be back to the USA though until there is a new federal administration.

Hi Denverguy—

I have passed through Chicago numerous times over the last 20 years, as I too seek out Amtrak adventures and Chicago is a common place to switch trains. I have ever overnighted there but it’s been mostly several hours to a half day. While this has allowed me to visit sites like the Chicago Art Institute and go up Willis (Sears) Tower, I typically beeline to either the lake or the Riverwalk for my time there so as to savour their unique beauty. Thanks for your words about a city I similarly always am happy to be visiting—Best wishes, Daniel

I lived in Chicago for most of my life until we move to the suburbs. We go to Chicago about once a month to visit with our son and his wife and the great thing about it is that there is always another great restaurant to try. When it comes to food, Chicago has a lot to offer. Beside the numerous wonderful steakhouses, there’s a lot of ethnic food as well and you can get many types of cuisines.

Then you have the lakefront and the various museums, and I mean, will class museums like the museum of science and industry, the museum of natural history, and the art Institute of Chicago. Then you can go to the Adler Planetarium or the Shedd aquarium.
And then you have numerous theaters for wonderful stage plays.

You can straw Michigan Avenue, go see the cloud gate and just have a wonderful time but yes, it is seasonal. Right now we’re in the grips of a cold spell, though it will subside in a couple of days. And my cold smell I mean windshields around 10 to 15° below zero.

The Travel magazine CN Traveler per readers Paul has Chicago voted as the best city or big city to visit nine years in a row. That should tell you something.

Good to know. I hope the Vance administration is next. That would be a good one.

I will be in Chicago next week for the third time at Christmas. The first time is was pretty cold. Between 0-15 degrees. In 2023, it was 45-55 degrees. This year it will be in the 40's. I am from Michigan so I am not a stranger to cold.

Chicago is a beautiful place at Christmas. One year I went for a long weekend at the beginning of December. That weekend was their holiday parade and the tree lighting. I was wondering on one of the streets off of Michigan Ave and came upon the staging area for the parade. I got to look at all of the floats before the big event.