Originally Posted by
touringuy
Hi all, my Canadian friend would like to know if it’s possible to fly from Toronto to ORD, enjoy a day or two stopover in Chicago, then continue on to Cancun from MDW.
Yes.
What documentation other than a valid Canadian passport is required?
None
Is it necessary to “pre-clear” for travel to both U.S. and Mexico visits when leaving Canada and would it be possible to then board a different airline a day or two later as my companion from MDW to CUN?
Your friend will clear US immigration and customs inspection at the US CBP pre-clearance facility at the Toronto airport. He will be in the US as a Canadian tourist. Nothing prevents him from taking any airline that he wishes to fly from Chicago Midway, or any other US airport, to Cancun.