Not necessarily. There has been a series of locks and canals cutting across Canada from the Atlantic to the Great Lakes since at least the 1860s (now the St. Lawrence Seaway); while that system probably couldn’t have handled ocean-going vessels at the time of your great-grandfather’s arrival, I find it not unlikely that he could have disembarked in Canada and hitched a ride on a smaller vessel all the way to Chicago.
How far back?
Parts back to 1632 in Farmington, Connecticut on my mother’s side.
On my father’s side, back to 1640’s in Rhode Island.
Interesting (to me) tidbits: Parts of my mother’s family also went the Scotland to Northern Ireland to America route. From another branch of my mother’s family we are distant cousins to the late Lady Diana Spencer. My father’s male line we have information back to 1752 in northern Virginia, after that no luck. One great^n grandfather (a different one) had nineteen children that we know of by three wives and one mistress, the last child born when he was 78. Another grandfather emigrated from Saxony in 1880 to avoid being conscripted into the Prussian army.
Genealogy is a family hobby and something that interests me quite a bit. What I wrote above is barely scratching the surface, I could probably write ten times as much with little effort.
Sorry, haven’t been back to this for awhile. Suggestions for. . .? A decent program that I’ve used for years is Family Treemaker. There are others, but this one has served me well. A good website is Cyndi’s List, which provides thousands of links to resources on the web including links to tutorials.
The cost to cross the Atlantic to Canada was also about half that to cross to the USA. A lot of people took that route. There is a resource called “St. Albans” that lists immigration to the US from Canada.
A guy approached our family because he thought he was related to us and offered to do a genealogy. The last name was Howard and he traced us back all the way to Hereward, an apparently famous guy in England because I have a book about him which I haven’t read. Some relatives from now to then were John Howard, Duke of Norfolk (mentioned in Shakespeare’s Richard III), two of Henry VIII’s wives (both beheaded), and Lady Godiva.
Turns out he had the wrong branch and wasn’t related to us at all, but he still finished the project. Several family members have copies of the history.
That’s my mother’s side. My father’s side I only know up to my great-grandparents, and that possibly they were of Irish descent.
Only two of Henry’s wives were executed: Ann Boleyn and Kathryn Howard. Ann Boleyn had a daughter by Henry, but as far as I know Kathryn Howard was childless.
On my father’s side, we can definitely go to the Revolutionary war (my Great^3 Grandfather). It’s a little dicey from there. Since Sherman burnt down the South Carolina Statehouse, there are a lot of records missing.
My Great^3 Grandfather, Benjamin Chew (not the famous one) was either the brother of or the son of Caleb Chew, whose grandfather, John Chew (Chewe) was a sailor, but not a colonist, on John Smith’s first Jamestown expedition. He later got a land grant from King James. There are records for his family going back to the 1200’s in England.
It’s just nailing down the exact relation between Benjamin and Caleb has been difficult.
Just last night I was handed some photos by my cousin’s ex-wife. She found them in a folder full of old papers. One of them was of my grandmother when she was a beautiful young woman, holding my then one-year-old mother on her knee. She also gave me the last will and testament of my great-grandfather. Finds like this make the treasure hunt worthwhile.
I’ve always liked Kahlil Gibran’s words: “Remembrance is a form of meeting.”
I have some cousins who are spread around Canada. I’m in California and never had much contact with them at all. Heck, I couldn’t even name them all. I met them a few times, and that’s about it.
I’m sure some of them have had kids by now, about whom I know diddly squat.
What I find weird is that there are these kids roaming around Canada somewhere, and we don’t even know each other even exists. Yet, those kids may someday learn on some family tree somewhere who their great grandmother is … and that person is my own grandmother, who I knew growing up. Boggles my mind.
When my mother got into geneology about a decade ago, we had a number of family stories we’d assumed were yarns. . . one about an ancestor who was a Civil War hero and met Abraham Lincoln, or the guy who ran a large Virginia tobacco plantation without slaves, or the guy who earned and lost a fortune, or the guy who had two wives who met at his funeral. They just sounded like tall tales.
-We found Civil War dude-- turned out he was a member of famous Irish Brigade. We got a hold of his wife’s widow pension application, and it was filled with letters describing his heroism, including one from this guy, who was a brigadier general. My ancestor was recovering from is four gunshot wounds at Point Lookout hospital on the day Lincoln came to tour-- so maybe they did meet after all.
-We found the plantation-- staffed entirely by free workers, most of them black, documented by 20 years of census and birth records. We have no idea why this family operated that way, but it turned out to be true.
-The bigamist turned out to be the same guy who earned and lost a fortune-- went from a poor farmer to a Chicago mansion to dying, literally, in the street in the Philly slums. He had 4 wives in four states, though who knows if they knew about each other. Every once in a while my mom emails me with “I found another wife!”
I really enjoy reading between the lines and imagining people’s lives. It can be fascinating, or tragic. My great-great grandfather had six additional children with his wife after his death (she just kept putting him on the birth certificate. . .). My great-something grandmother lost 7 of her 8 children in the space of two weeks to scarlet fever, and then died herself, six months later, of a botched abortion. (Her only surviving child, the oldest, became The Bigamist)
We’ve found two or three more unrelated bigamists and a whole host of illegitimate children and people who got disowned for marrying the wrong person. (Plus a nice selection of con men and criminals). Interesting pedrigree I’ve got there. . .
See, that’s the kind of stuff I’d love to find, but I suspect my ancestors were all stoic, boring, farm families.
I think my favorite genealogy story is from a commercial advertisement for genealogical software. This guy farts around on the internet for a while, then comes out into the living room and announces to his kids that they are descended from one of the Wright brothers. Who doesn’t know it when his grandfather or great grandfather is one of the most famous people in the US? You’d think he’d remember having gone to Grandma’s for Thanksgiving and seeing all the newspaper clippings…
Oh, yeah. I had one of those moments this past weekend.
In 1836, a group of delegates met at Washington-on-the-Brazos and declared that Texas was independent of Mexico and a free country. Col. William Fairfax Gray was present during the convention and recorded it in detail in his diary (the diary account, in some cases, is more accurate than the minutes kept by the secretary). Gray is my great-great-grandfather.
The state of Texas has preserved the old site of Washington-on-the-Brazos, including rebuilding Independence Hall on the exact site of the original. We were there this last weekend and it was eerie to think that I was walking the exact location that Gramps had.
I was close to my grandfather; he loved to go fishing with me; took me to his work, etc. But he told me very few stories about his family, and never mentioned the fact that his own grandfather (still alive when my grandfather was 23 years old) had been a United States Senator and one of the most prominent men in my grandfather’s birth town.
(If my own father was aware of the connection, he never mentioned it to me; and yes, the connection is completely secure, not some genealogical conjecture or fantasy.)
In fact, it looks like you could trace it all of the way back to Seung-gae Lee with just minimal additional effort. 
Very cool, though, actually.
On my mom’s side, she traced one branch back to the 1400’s in France (well, actually, she simply received much of the older info from someone else in a different branch of the family who had already done much of the legwork).
If your Grays originally came from New England or are an offshoot of that family, then we’re related. My Grays immigrated to America (probably from Scotland) in the late 1600s, migrated from Massachusetts through New York, then on to Ohio. There is a very populous Gray family line that is from Pennsylvania, but not related to me.
According to my grandmother, my ancestors in the 1800s were a bunch of horse thieves.
I always thought my family was all post-Civil War immigrants and just a few years ago, I learned how wrong I was.
Someone did an extensive family tree and one branch goes all the way back to the 1640s, I believe. I’m apparently 12th generation American, which surprised me. As my family has said since, you’d think if we’ve been here so long we’d have some money.
I found out recently that my great-grandfather was apparently somewhat wealthy (self-made) and did business with the Kennedys before the 50s, including visiting them on the Cape. His business partner supposedly engaged in some illegal business practices, bankrupting him, and one or both of them did some jail time. I accidentally came across my grandfather’s brother’s name on a WWII memorial last summer too, which I did not know about.
In another branch, which goes back to the 1790s, we did some immigrating to the US and Canada from Ireland and bounced back and forth a lot. So there are tons of Canadian relatives, but tons of US ones, all of the same generations. My favorite is that in my great-grandparents’ generation, three brothers married three sisters, so that’s what makes the family extra big and why everyone is so closely related despite the distance. It also explains why my grandmother’s married female blood relatives all had my grandmother’s maiden name. We were and O’ family at some point too and that got dropped.
My other side of the family doesn’t have the history written down and I don’t trust most of the stories I’ve heard. Like supposedly our name was too ethnic and was changed upon immigration, but when I’ve googled the supposed real spelling, NOTHING comes up, which makes me think we’re spelling it wrong and wonder what else we get wrong. Supposedly we were wealthy farmers, but then why would we leave? If it is true, I think there were some shenanigans going on, as that branch of my tree is sketchy. Like I know my great-grandfather’s brother left his wife in the old country and went to Canada and got himself another wife. So who knows what my great-grandfather did.
Another branch confuses me the most. We say we’re Russian and the family was Russian Orthodox, but we’re really from the Ukraine. So I don’t know if we just say Russia as a euphemism for USSR or what is going on. The name seems to be Ukrainian, but it seems they spoke Russian. Supposedly my great-great grandfather served in the royal army and I always suspected that the revolution was around when they left. I know my great-grandmother was a bootlegger during Prohibition and the family would distill vodka in the bathtub and bottle it up and hide the wares in my grandmother’s baby carriage for distribution to the neighbors.
I am fascinated by these things. I guess I should take up the responsibility and gather the stories and see if I can match them up with true facts and find out proper spellings and dates.
Catherine Howard. But that’s not who I meant, although she’s in the tree.
Anne Boleyn is the daughter of Elizabeth Howard and Thomas Boleyn. She was the granddaughter of Thomas Howard, the son of John Howard who I already mentioned.
That’s who I meant. 
A few years ago I found out that I’m descended from Col. Timothy Matlack (mentioned in National Treasure as the engrosser of the Declaration of Independence). About a hundred years ago, a member of the Matlack family put together and published a history of Col. Timothy, which included a family tree that traces the Matlacks back to early 16th century England.
I’m sure the Matlacks are scattered far and wide now, but my branch of the family has been right here in the Philadelphia area for over 300 years now. In fact, I grew up in the same town where William Matlack (Col. Timothy’s grandfather) first worked when he came to America.