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I've driven across the border before - Detroit/Windsor, and had generic tylenol w/8mg codiene, 50mg caffiene. The bigger deal was personally crossing, not what I carried. You'll need your drivers license, birth certificate, and if your name changed when you got married - your marriage certificate. If you have a passport - a passport alone is enough. I had more trouble getting back in, traveled with the kids and then husband, and they had us leave the car and took the kids in a different room to ask if we were their parents... thank goodness my older one wasn't mad at us that day..
From Chicago it's about a 5 hour drive (if the skyway isn't under construction).
Don't go to Wal-Mart, they ask where you're from... only sell the little 50ct bottles to you and look at you funny.
There is a drugstore all over - kind of like a big Walgreens or CVS... purfume is cheaper there too... I might suggest getting 2 bottles from each branch you happen to stop at....
There is a great Museum of Modern Art (FREE!) and fun festivals during the summer on the shore. Tunnel BBQ has awesome ribs, and the Raddison Riverfront (parking extra) has a nice pool.
It's really not a big deal, only if you make it one. You can even bring home a Havana for that cigar smoking uncle...
It's a great cheap way to take the kids to a foreign country.
The casino is kind of fun too...
If you have any questions feel free to pm... I'm only here once a week or so though so I'm not ignoring you.