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We've checked a pack n play-- no problems there. Just on and off the carousel like any piece of baggage. And most pack n plays come with a bag so you don't even have to do anything special to it, just attach a luggage tag.

Double stroller-- this is so important. From the research I've done, there is only ONE double stroller under the restriction of 20 lbs-- it's some folding umbrella double by Jeep. BUT I have heard that American Airlines is the only airline that has this restriction. We flew one way with Jetblue and was able to gate check the stroller, and the other way with American and we had to check the stroller with baggage. We were so upset because then we had to carry our kids through the airport. They were too big for baby carriers at that point.

I would check with the airline you are flying, and the safest thing I believe is to fly with two single umbrella strollers (you can buy a clip that connects them to be a double stroller) OR you can try one umbrella stroller and something like a gogobabyz car seat carrier. We've had good luck with that when traveling with two kids roughly the same size.

We just recently gate checked a double stroller on Alaska Airlines - it was a maclaren, with no issues and no fees. We used a gate check bag. No damages even though I was nervous about that!

I have flown with my city mini gt double before but always checked it. Our travel crib was checked as well. I did not have a fee for either and this was on Southwest and American. I used the travel bag for my city mini and it was well worth it.

@bluestriped bee: I was actually just looking at umbrella strollers and noticed this one in my Amazon search and thought of this thread. Under 20 lbs and pretty highly rated (plus not expensive!).

http://www.amazon.com/Delta-Children-Street-Stroller-Black/dp/B003TRVFJG/ref=sr_1_14?s=baby-products&ie=UTF8&qid=1435176618&sr=1-14

We fly all the time with our double stroller and both car seats. Sometimes we check in the stroller and use our carriers, othertimes we gate check the stroller. We've never had any issues.

@bluestriped bee: We've travelled a ton with our bjorn travel crib. Only on international flights were we allowed to take it for free. Domestic, we found it was cheaper to rent a pack and play where we were going ($35 ish) vs checking it both ways ($50 ish). We haven't flown with our double, so no help there, but when gate checking baby items in the past we either just show them in trash bags or use bags the airline provides. We had a cup holder broken on the stroller once. Out of many, many flights I suppose it could have been worse.