A wheeled cooler can make it a lot easier to get cold drinks from point A to point B, and you've got plenty of options that won't cost you that much more than a regular cooler. Take the Igloo Latitude, for instance. At a price of $50, it offers a very sizable 60 quarts of storage space for whatever you want to keep cold, plus it rolls around like a suitcase so you won't have to carry it so much.
Personally, I like the appeal of a rolling cooler, but the Igloo Latitude isn't one that I'd recommend. For starters, the design feels flimsy to the touch, particularly the telescoping handlebar and also the lid, which comes right off the hinges when you yank on it. Even worse, the performance was borderline pitiful, and barely any better than the dirt-cheap Igloo Island Breeze and Rubbermaid Ice Chest coolers, which both essentially flunked my tests.
Here's another fun fact from those cooling tests, where we filled each cooler with 3 lbs. of ice, then tracked the ambient temperature inside for 48 hours: the Igloo Latitude returned to room temperature faster than a throwaway Styrofoam cooler that I picked up at the grocery for $4. If that isn't enough to get you to steer clear of the Latitude, I don't know what is.
For much better performance at the same price, I strongly recommend the Igloo MaxCold Cooler, which aced my tests and actually costs less than the Latitude at $45. It isn't wheeled, but Igloo sells wheeled versions of it, and while I haven't tested those out just yet, I have to think that they'd be a lot better than the Latitude.
For something more high-end, you could also consider the Rovr Rollr 60, a rugged rolling cooler that offers heavy-duty wheels, a durable, rotomolded design and optional extras like a hitch that lets you tow it behind your bike. The rub is that the Rovr costs a very hefty $399 -- for something more affordable, consider the Coleman Xtreme Wheeled Cooler, which costs $45. It didn't ace my tests, but it did a heck of a lot better than Igloo.
Want more info on coolers? Check out our full roundup post for more tips and buying advice.