Yes..winds certainly influence monarch flight speed and travel. While I have had a number tagged monarchs recovered along the north shores of Lake Ontario (including Port Hope, Oshawa (Intrepid Park), some attempt to cross Lake Ontario when weather conditions are favourable, and as recently as last fall, I had a Presqu'ile released monarch photographed by another Monarch Watch tagger at the Stirling (New York) Nature Centre on the south shore of Lake Ontario.
Longest distance I recall a monarch being recovered/spotted from one day to the next was an individual, probably blown by the winds, was a distance of about 276 miles.
In 2005, at Shipyard Park on the Oakville waterfront, I spotted a tagged monarch on one of those long, tall rows of buddleia (long since gone), and discovered it had been tagged by 70 year old Julie Clemens, a Monarch Watch tagger in Cleveland, Ohio. It is suspected that this monarch was blown about 165 miles to the north-east by the remnants of Hurricane Katrina.
Toronto, Ontario, Canada