The marketing department wants you to believe you need to drop four bills on a rotomolded box to keep a sandwich cold. I've spent 15 years guiding on Lake Superior and testing coolers in hitch baskets, craft fair parking lots, and the back of a Jeep overnight. The truth is, the best cooler under ~$100 doesn't exist, because there are about five of them, and they all do different jobs.
The Titan Zipperless HardBody Cooler (Check price) is the best cooler under ~$100 I've tested, because it combines the clean-ability of a removable liner with ice retention that held up over a 3-day weekend.
Here is the short list, winner first:

Titan Zipperless HardBody Cooler, Keeps Ice 2 Days
Zipperless lid, removable liner, held ice for 3 days
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Coleman Classic Series Insulated Portable Rolling Cooler with Wheels, Leak-Resistant Outdoor Hard Cooler Keeps Ice up to 5 Days
Check current ice retention claims
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Coleman Chiller 9/16/30/48/60qt Cooler with Ice Retention, Leak Resistant, Great for Camping, Concerts, Sports, and More
Kept lunch cold 10+ hours, great price
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Igloo Marine Cooler | Insulated Hard Shell Ice Chest |Great for Fishing, Camping, Boating, & More
Built for fish, drains fast, tough exterior
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Coleman Classic Series Insulated Portable Cooler, Leak-Resistant Outdoor Hard Cooler Keeps Ice up to 5 Days, 52/70/120/150 Quart
Solid basic performer, leak-resistant
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I start Thursday and end Sunday. That's the gold standard. Three days of real sun, real food, and a client's catch on the line. I measure ice retention in a 70-degree room, not a climate-controlled showroom.
I count cans. I check if the lid stays open. My dog Ivy, a 65-pound lab mix who thinks every cooler is a bed, handles structural integrity: if the lid survives her lying on it, it'll survive your tailgate.
Titan by Arctic Zone Deep Freeze
The zipperless lid and latching system are amazing. No more fighting with a stuck zipper when you've got a walleye in one hand and a koozie in the other. But the genius feature is the removable HardBody liner. You will never have stinky smells from foods sinking into side walls. I've cut open enough coolers to know that's where manufacturers cheat, and this one solved it.
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One golfer overthought his purchase so hard he measured the interior and posted the can math to help somebody out. Ten tall cans standing, or twelve normal cans laid down, plus an ice pack on top. With the SmartShelf tray in, you lose a row, so plan accordingly. The sandwich tray is genius.
Compared to my CORE (more expensive), the CORE kept things cooler. It has a magnetic lid with a heavy duty waterproof zipper. But the Titan does 80% of the job at 40% of the price. If you're in the ~$50 to ~$80 range, this is the one.
Coleman Classic Series Rolling Cooler
The wheels handle sidewalks, asphalt, and really muddy ground. I've rolled it across craft fair parking lots and boat ramps without a problem. Ice lasted 4 days in my testing, and even 3 days in 80 to 90 degree heat at a craft fair with constant in-and-out access.
One family drove from Arizona to Wisconsin during the hottest week of summer, strapped it to a hitch basket, and after 3 days on the road, some food was almost frozen with barely any meltwater.
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But the lid won't stay open. There's no way for it to stay up without holding it. That's an annoyance when you're trying to grab a drink with one hand and hold a plate with the other. It's a stretch to call it a dealbreaker, but it's a real flaw.
At ~$65, this cooler costs less per day of a three-day camping trip than a single round of drinks at the bar. The ~$300 cooler has to be four times better to justify that gap. It isn't.
Coleman Chiller
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This is the workhorse for truck drivers and workday lunches. One guy kept his lunch cold at least 10 hours with a couple ice packs in summer. Another got 3 days of cold food out of it. For the price, that's excellent performance.
But getting 3 full days in the sun like advertised is a stretch. In a 70-degree room, the ice melted by day two. The water stayed cold, but let's be honest about what "keeps ice" means. And the lid will close by itself, which is an annoyance. I'm trying to grab a sandwich, not wrestle a bear.
It's great for what it is, but don't believe the marketing. At ~$25, it's a steal for a 9-to-5 cooler.
Igloo Marine Cooler
This one is built for fish. The drain plug is in the right place, and it's designed to let meltwater out without soaking your trunk. I've used it on charters where the catch went straight in, and it holds up. The exterior is tough, and it's got the ice retention to handle a day on the water.
But it's heavy when full, and it's overkill for a tailgate. If you're hauling walleye, this is the one. If you're hauling seltzers to a golf course, you're carrying too much cooler.
At ~$85, it's a specialist. I respect that. But for most people, the Titan does the same job with less weight and better clean-ability.
Coleman Classic Insulated Cooler
The basic Coleman. No wheels, no fancy features, just a leak-resistant box that keeps things cold. One reviewer used it as a daily driver and it held up fine. In my testing, it's the baseline. It does what it says, no more, no less.
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The problem is the lid. It flops hard when you open it, and you have to hold it up with one hand while you dig for a drink. That's a daily annoyance that adds up.
At ~$45, it's a fine choice if you need a simple cooler and don't want to think about it. But the Chiller does the same job for less, and the Titan does a better job for a little more.
Compared to the premium stuff
Forget the ~$300 coolers. I've borrowed a friend's ~$400 rotomolded monster, and it kept ice longer, but not 4 times longer. The premium brands are real, but they're not necessary. You're paying for peace of mind, not performance.
My CORE (more expensive) kept things cooler and has the magnetic lid with a heavy duty waterproof zipper. It's a great cooler. But it's not 4 times better than the Titan. If you're already spending that much, you might as well get a rotomolded Yeti. But if you're asking me, the Titan does 80% of the job at 40% of the price.
Should you buy it?
If you want the best cooler under ~$100, get the Titan by Arctic Zone. It's the one I reach for on weekend outings, and the removable liner means it won't smell like last week's catch. If you need wheels and you're hauling gear across a parking lot, get the Coleman Classic Rolling. If you just need lunch to stay cold until 5 p.m., the Chiller is all you need.
I'm in the middle of a summer-long cooler shootout. I've got a Coleman Classic Rolling, a Coleman Chiller, a Titan by Arctic Zone, and a Hulongo backpack in rotation. I'm testing them on 3-day trips, in 80 to 90 degree heat, and on real terrain. I'm also measuring interior dimensions to settle the how many cans fit question once and for all. Check back later this summer for the full ice log.
