Travelling with 2 check-in bags

One option is to strap your bags together, so you can roll it like one suitcase. USA Today has step-by-step instructions, and you can either use a regular long luggage strap, or Travelon's "Multi-Bag Stacker" strap ($12) precisely for this. TL;DR version:

1. Pull out handle of bigger bag.
2. Place smaller bag on top, resting against handle.
3. Tie them together.

Obviously this works better if the 2nd bag is smaller, and for better balance you'll want to pack the heavy stuff at the bottom of the lower bag.

Alternatively, you can pull one suitcase and push the other in front of you. This is viable for short distances on level ground, but not realistic if navigating several miles on city streets.

I've done this once or twice and it's generally horrible. Some tips:

• you have two hands, so you can generally handle two things, though doors and whatnot will provide a challenge. But you really can't do three. So your carry on should either be a backpack (so it doesn't use up any hands) or be strapped to one of the suitcases.
• the suitcases need wheels.
• ask people to help you: "Can you open that door for me?" or "could you push the button for me?" will make you much less frustrated
• if you have to navigate stairs, you will probably have to do it in shifts - try not to get too far from either bag or they may be stolen.
• don't feel guilty about being slow. You have every right to be on a sidewalk or platform.
• if you chain the bags up somehow, do accept the fact that it might not work in some circumstances and be able to get them apart quickly
• you may want to use a taxi for some small part of the trip to get around a particularly hard-to-navigate portion, and use public transit for the rest.

Finally, pull up a picture in your head of someone about your age who is struggling with a 50 lb suitcase, a baby stroller, a diaper bag full of baby stuff, a carry on bag for the plane, and oh yes, an actual baby, who is crying. Think about this person every time you start to feel sad about lugging two 50 lb suitcases. It could be worse.

You can check with hotels near you (or with the airport) if there are shuttle buses that go to hotels on demand. You can then take a taxi just up to the airport and then the shuttle bus the rest of the way.

Another way you can do it is to only take one bag at a time, and use an airport locker to store one of the bags, and then go and pick up the other bag.

I have used the following Collapsible Dolly Cart, which could carry all three Bags easily. http://www.handtrucksrus.com/crashdetail.aspx?ID=371&cx=rwm

It was a successful experiment.