I accidentally discovered how to get free checked bags when flying. I'm not saying this is guaranteed to work 100% of the time, but it worked for me every time. Normally when traveling with a stroller, we also have the stroller bag. That's a great place to shove a bunch of extra stuff in as well. However, here's what I figured out in addition if you've got too much stuff.
1. Don't check in at airport, use online check-in and get mobile boarding pass and go straight to security at the airport.
2. Bring your luggage through security. It still needs to be a reasonable size, but don't worry about weight.
3. Tell the gate agent you want to gate check so you can save space for others in the plane. They'll give you tags and take your bags at the gate. Flights seem to be always fully booked now, so the agents are under pressure to make as much space as possible. I usually just say that I either want to make space for others, or I've got my hands full with the kids, or I just ask them to gate check it along with my stroller. Tell them you want to pick it up at the luggage carousel in your destination airport.
Another cool trick is to use a string backpack, stick your densest items (laptop, tablet, etc) in there, put it on your back and wear your jacket over it when boarding.
It worked on a bunch of strict airlines. Never had an issue and was overweight and over quantity on all of them. Never had them weigh or measure my luggage at the gate since they just assume I'm going to give them a consolidated piece(s) of luggage to put in the hold and would therefore likely go over the limit. In addition, I'm noticing a trend in airports where the gate agents don't necessarily work for the corresponding airline. They just work for Swissport or other general ground services crew and don't particularly care or know every specific airline and/or flight policy.
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