Sadly it's almost as long for me to get to Montreal as it is to get to Chicago or I would have tried to come see you. I love Old Montreal - check out this list
https://www.tripadvisor.ca/Attractions- ... uebec.html - the first 3 are all worth doing. I used to go for business and stayed downtown at the Queen Elizabeth hotel (located over the train station so uber convenient) but a bit of a hike to Old Montreal and more of a financial area.
And everyone will great you in French but will switch to English quickly.
Enjoy. Weather wise it's similar to Chicago winters so you won't be shocked.