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Fucking tour guide right here. Do you have a double decker? Is there a kiss at the end?If I were you I would get an early train in, walk down Jackson to Columbus, see the Lincoln, and the Buckingham Fountain, keep going south to the Shedd / Field. See those, get on the water taxi to Navy, take an uber from there to Millennium/Maggie Daly (even tho it's only a mile, so you could walk if you wanted to) and then to Chintown (if you still want to go there). I know that's kind of counter-intuitive because you're going north to come back south, BUT you get to see the parks, museums, city from the water, and Chinatown if your lady's heart is set on it.
It's a lot to cram into one day, but it can be done!
That's hugely useful info, thanks
Chicago... Come for the food and stay cause you got murdered