Upvote:2
If your flights are on the same booking, your luggage will be transferred to your next flight so you don’t need to worry about that.
As your flight is with United airlines, all of those leave from terminal 1 so you don’t have to pass security to change terminal.
As you are travelling with a 2 1/2 year old with a car seat you should probably contact the airport to arrange some provisions regarding that matter.
Positive Passenger Bag Matching will prevent your flight leaving without your bags on it. After all, the connection is doable since it was sold together as a ticket but the child makes it tight.
Honestly, if you contact the airport it should be doable buts it’s your choice if you want to reschedule your flights.
Upvote:2
Going south and entering the US, you will have to pass US Immigration. You'll do so at the US CBP Preclearance Facility at the Winnipeg airport, before you board your first flight. That makes the Winnipeg > Chicago flight effectively a "domestic" US flight. When you arrive at ORD, you'll just deplane and find your departure gate. You may have to pass security again, but United thinks you have enough time to do that, as their (United's) computer allowed the route on a single ticket. Because both flights are on United, your baggage will be checked-through directly from Winnipeg to Florida, and you won't see it in Chicago.
Coming back you have a shorter connection, but as above, United thinks there's enough time. And if you don't make the ORD > YWG flight, United's responsible to get you there and will put you on the next one. As above: because both northbound flights are on United, your baggage will be checked through and you won't see it until you arrive back in Winnipeg.