I'm contemplating taking a trip to Chicago (from DFW) on July 22, spending 3 nights, then taking the Amtrak Zephyr to San Francisco (leave Chicago July 25, arrive in the Bay Area July 27) then spending a couple of nights in San Francisco before flying back to DFW on Monday July 29. Besides the train trip, the other key points to me are attending a Cubs game at Wrigley (the Brewers are in town during my stay, probably would shoot for the day game on Wednesday the 24th) and seeing Alcatraz. I've never been to Chicago, and have only driven through San Francisco on a driving trip down the West Coast from Seattle to San Diego in 2021.

I'd like to hear lodging suggestions for both cities. I'm not opposed to spending for a well located special hotel, but I'm OK with something more moderately priced as long as the location is good. I'm a Hilton guy, so naturally the Palmer House and the Drake popped up on the app for Chicago. For San Fran, all the Hilton properties seem to be downtown, but for what I want to see, I wonder if the Fisherman's Wharf area might be better (there seem to be a number of Marriott properties in this area, which also works, but I'm not determined to chase points and would consider any label).

Anyone ever done the train trip? I've watched a number of videos and know what I'm in for.

The Drake is a great option. I lived right across the street for 15 years, and the Drake is my go to for Chicago now. It is dated, but the location is great, and the prices are really good too.

The executive martini at Coq d'Or is world class, if you are into that.

You need to do an architectual boat tour while in Chicago

Alcatraz at night is better than during the day

Day Game at Wrigley on a summer afternoon is the way God intended for baseball to be played.