
WINNER Scooter’s Frozen Custard1658 W Belmont Ave, 773-244-6415
You can try to find a shake that’s denser, thicker, richer or more over the top than the vanilla Boston Shake, made with sumptuous frozen custard, then topped with even more custard, hot fudge and whipped cream. But seeing as how this is more prayer-that’s-been-answered than actual milk shake, we’re convinced this is the one. Just stop searching already and give in. $5.35.
#2 Eleven City Diner1112 S Wabash Ave, 312-212-1112
It’s only a couple of years old, but this South Loop eatery strives for old-school charm. Thus, this classic milkshake is so thick it takes all the air in your lungs to suck it through the straw. But bring a friend to share it with you and victory will be yours. $5.65.
#3 Perry’s174 N Franklin St, 312-372-7557
You might think you can’t have a chocolate shake after eating one of Perry’s signature “sandwiches as big as your head.” But if you grab the glass with both hands and bring the sweet stuff to your lips, you’ll see: It was all in your head. And now it’s in your stomach. $3.30.
#4 Salt and Pepper Diner3537 N Clark St, 773-883-9800
What’s a diner without a good milk shake? Nothing, that’s what. So thank the milk-shake gods that these simple, old-school vanilla (and chocolate, and strawberry, etc.) shakes are keeping this 42-year-old classic popular. $2.95
#5 PotbellyLocations throughout the city
It’s a chain, yes, but it’s a Chicago chain, and it makes a simple, cold, sweet and overall damn good shake. Plus, you gotta love a fast-food joint that takes the time to garnish the shake with those cute miniature butter cookies (or, for the Oreo shakes, mini Oreos). $2.69.
Now I can die. I just had a peanut butter chocolate malt at R J Grunts. I went into another zone, maybe heaven, after just one sip. Nothing around me was as important as that drink. Don't think about getting the diet version, you only live once.