Best way to move a few items across Chicago?

For just a couple boxes and a small bed, I’d probably skip the movers unless you really want the convenience. A friend with a decent-sized car or a quick rental from a place like U-Haul could save you a good bit of money. Just make sure you’ve got a way to secure the bed so it doesn’t shift around during the drive.

Funny enough, I once moved with even less — just a couple bags, my guitar, and my Adidas x Oasis Tour Jacquard Jersey stuffed in a duffel. Sometimes the small moves are the easiest because you can knock them out in one trip and be done.