Canadian to CUN with ORD stopover
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. What documentation other than a valid Canadian passport is required? 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? Other option would be to just meet in CUN, but we’d prefer to fly together the leg from Chicago using my companion pass. Thanks for any expert advice!