Mrs. Levy's Delicatessen
Sears Tower, Chicago
Since Mrs. Levy's was in Sears Tower, I had assumed the restaurant was going to be a tourist trap with substandard food. How wrong I was! The restaurant apparently has been around for a while. It has quite a bit of character (along with a lot of celebrity and semi-celebrity autographed pics on the wall). I got a Walter Raymond sandwich - basically a turkey club with Russian dressing, fries and a fantastic chocolate shake. The shake not only came with whipped cream, it also was a topped with a triangular cookie wafer and a cherry! I don't remember the last time I had a shake topped with a cherry. I don't like cherries, but that's besides the point. The wafer was excellent, especially good when covered in a little whipped cream and shake. Besides the toppings, I also got the bonus shake in the steel mixing cup. Heartily recommmended!
1966 W. Lawrence, Chicago
This restaurant got me (re-)hooked on shakes. The shakes aren't always consistent (it depends on which waitress is making the drink, and the amount of chocolate used varies) but they are always plentiful. You get the shake glass, and also a stainless steel mixing cup half-filled with more shake! Sadly, this practice of giving the customer two shakes for the price of one is getting harder and harder to find, but at the Ravenswood you can be confident that you'll get what you pay for. Don't forget to ask for whipped cream; sometimes they forget.
4008 N. Lincoln, Chicago
The Lincoln Restaurant shake has no mixing cup bonus. It's just one shake glass, and it disappears quickly. You might want to request that you get the drink with the meal, or else it will be gone by the time you're ready to eat. Despite the meager portion, the Lincoln shake has a very smooth texture, and a lovely subdued taste. The best part of the shake, however, is the whipped cream, which is thick and quite wonderful. It puts Cool Whip and the like to shame. If you decide to try the turkey club/fries/shake combo, the All American Club is nice (it's a turkey club with cheese and ham) and the waffle fries are excellent.
Potbelly Sandwich Works
Several locations in the Chicagoland area
Potbelly's is a sandwich shop that makes a pretty good east-coast "grinder." The shake comes in a deceivingly squat (is it possible to be deceivingly squat?) paper cup which actually contains quite a bit of good shake. It's on the thicker end of the consistency spectrum, and lasts for a good amount of time as a result. One nice touch is placement of two small butter cookies ringed around the straw. If you don't feel like a shake, they do have IBC root beer in a bottle.
20 E. Jackson, Chicago
"Arby's?!!" you ask? Yes, Arby's! I know it's the ugly backwoods cousin of the fast food chain family, but give it a chance. As far as I am concerned, they make the best fast food shake, using softserve ice cream and chocolate syrup, as opposed to the mix-with-plastic-bubbles shake you'll find at McDonald's. I like getting a Chicken Cordon Bleu sandwich with regular fries (none of those curly seasoned fries, thank you) with a chocolate shake. Be forewarned that this is a rather expensive lunch, costing around $7.00. Also, another warning. Some months ago I went to an Arby's on Ashland Avenue and ordered my usual, and was horrified when I took a sip from my shake. It was just like a McDonald's shake! A crappy pre-mix! It appears there are some Arby's using a pre-mix, and some using softserve ice cream. Make sure you get the good stuff.
Susie's Drive In
4126 W. Montrose, Chicago
Susie's is an old-fashioned walk-up hot dog stand. I don't know how long they have been there, but it's been a while. They have a counter and some stools in cramped quarters inside, some tables outside, an outside pick-up window, and of course a drive-thru. During my trip to Susie's, I personally did not purchase a shake. I actually got a "Gyros Master" special, which comes with excellent hand-peeled fries and a Coke. I sampled my girlfriend's chocolate shake, a bargain at $3.43 for a liter of beverage (I talked her into getting a larger size so I could have some). Being a fast food joint, the presentation of the shake suffers because it comes in a styrofoam cup rather than the traditional shake glass found at your average diner. Still, the shake was tasty. However, the taste of chocolate seemed to come from the chocolate ice cream used in the shake, rather than syrup (though I could be mistaken). I like the taste of a syrup-based chocolate more, but that's just my personal preference. One thing fun about Susie's is that they always seem to be coming up with new dishes and beverages to serve the hungry public. I intend to try the Green River shake next time, whatever the heck that is.
112th and Broadway, New York City
On a recent trip to NYC with my girlfriend, it turned out that our motel was very close to Tom's Restaurant, which may be more familiar to you as Monk's Restaurant, the diner that the gang from Seinfeld used to hang out in. We were in the neighborhood, so we thought we'd drop in. The restaurant was refreshingly untouristy (is that a word?), and the meal wasn't that expensive. Lunch was under twenty bucks for both of us, including two chocolate shakes. They didn't have a turkey club (though they had a turkey sandwich) so I ordered a cheeseburger, which unfortunately was fried rather than grilled. The shake was pretty good, nothing incredibly spectacular, just a good straightforward chocolate taste. They also gave us the extra mixing cup with some more shake, and the service was excellent.
Medici on 57th
1327 E. 57th Street, Chicago
This restaurant is a stone's throw from University of Chicago, in the scenic Hyde Park neighborhood. I got a turkey club, fries and a chocolate shake. This was a particular case where my personality clashed with the shake. It was a little bitter as a result of being heavily saturated with cocoa. It was actually too chocolatey for me, and this pretty much overwhelmed all other aspects of the shake, the creaminess, the ice cream, etc. I think that perhaps if they served the shake with whipped cream the cocoa taste could have been cut a bit. I'm not saying that the shake is bad, it just wasn't the right shake for me. They do give you a full stainless steel mix cup of beverage, so that's a definite plus.
NEW McDonald's REVIEW
McDonald's is making pretty good shakes now! I think they are using their soft-serve ice cream for shakes; gone are the mysterious "flavor bubbles." The chocolate shake is now pretty tasty, and not much worse than the Arby's shake.
McDonald's (old review)
I loved McDonald's shakes when I was a kid, but then again I loved Gilligan's Isle, too. The shake isn't very cold, it has a faux-creaminess and thickness that doesn't compare to the natural creaminess of ice cream, and it doesn't even taste like chocolate. I don't know for certain how these shakes are made; if anyone would care to inform me of the process, or confirm that there are indeed plastic bubbles in McDonald's shakes, please do so.