Still worth doing though, even if a bit short. Definitely on the list. It’s a lot easier flying to the east coast/Chicago in terms of time and jet lag. This will be my fifth and my wife’s third time to Chicago in 4 years, I absolutely love it, and am lucky that I can tag a couple of days there on to work trips, if I get the flight routing right.
I’m growing to like tours. The architecture boat tour on the Chicago River is so good I’ve done it twice, had a truly memorable tapas, wine and history tour in Barcelona (6 in the group),and will probably do the Circle Line boat trip around Manhattan in a few weeks.
One recommendation for your New York trip is to walk the High Line, if you haven't done it before.
https://www.thehighline.org/
It starts near Greenwich Village and ends not far from the Circle Line pier (only about a mile and a half), so you could make it coincide with your boat trip.
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