Over the past year I've eaten at more steakhouses than I have in the previous 30 years of my life combined. The purpose of this extremely hard work (hey, that's a lot of beef!) was to find the best dry-aged steaks in Chicago, and I never lost sight of that goal. But as most people know, the à la carte system is still a fixture of every steakhouse, which required me to consider a genre of food I'd never really considered before: steakhouse sides. Instead of cursing the thought of adding an $11 bowl of spinach to the already massive bill (or just adopting a meat-only diet) I decided that it would be interesting to actually give these neglected add-ons a shot.
Since steakhouse menus are so uniform, I made sure to order the exact same set of dishes at each place. That lead me to a few months spent contemplating the finer points of shrimp cocktails, wedge salads, and creamed spinach. While I had a sort of a perverse curiosity to see how different places would execute these very simple dishes, I have to admit up front that I also genuinely enjoy all of these. Perhaps it's the presentation or the pleasure of cutting through crunchy iceberg lettuce with massive knife, but I love wedge salads more than anyone I know. The same can be said about creamed spinach, especially when it's bright and vibrant green. And who doesn't love a good shrimp cocktail?
So, after you take a look at all those beautiful slabs of meat, scroll down to see what sides to pair them with.
Best Shrimp Cocktail: Chop Shop
Of all the dishes I tried, the standard of the shrimp cocktail was probably the highest. Every single place served enormous shrimp that were plump, juicy, and cold. But even with the tough competition, Chop Shop's version managed to stick out in two important ways. First, it's only $12, which is a genuine bargain, especially compared to the $21 I spent at Smith & Wollensky for three shrimp that weren't even deveined. Second, Chop Shop's cocktail sauce is the most complex and alluring, with just enough horseradish to get your nose running. Though a great starter for the steak, this appetizer is worth its own special trip.
Chicago Chop Shop, 2033-35 W. North Ave, Chicago, IL 60622 (map); 773-537-4440
Best Creamed Spinach: Smith & Wollensky
You might have noticed that I didn't mention Smith & Wollenky in my list of the best dry-aged steaks in Chicago. That was not a mistake. Smith & Wollensky may dry-age beef at each of its many locations, but I had a hard time noticing any intricacies in the beef because it was so poorly cooked and underseasoned (click here for visual proof). And as I mentioned above, the three undeviened shrimp for $22 isn't a particularly good deal (sad, right?). But I have to hand it to Smith & Wollensky for serving the best creamed spinach.
No other category was as clear cut as this one. Most were far too creamy, and some were little more than bowls of cream with a few specks of green mixed in. But Smith & Wollensky's version was bright green and vibrant.
Smith & Wollensky, 318 N State St, Chicago, IL (map); 312-670-9900
Best Wedge Salad: Bavette's
I never encountered a straight up terrible wedge salad. I mean, it's not that hard to serve a freezing wedge of iceberg, spoon on blue cheese dressing, toss in a few croutons, and call it a day. But that also meant that most versions were just slightly above average—right at that point where I noticed the high cost and knew I could probably make the same thing at home for far less. The only exception was at Bavette's, which not only served the best wedge salad by a mile, but it was also one of the best salads I've tried in recent memory.
What really set this salad apart was the dressing. Instead of a thick blue cheese, Bavette's went with a thinner Ranch. This looser dressing was able to seep into the crevices of the salad leaves, flavoring each bite. Of course, the 1/2-inch thick housemade bacon didn't hurt matters.
Bavette's Bar & Boeuf, 218 W Kinzie St, Chicago, IL 60654 (map); 312-624-8154
Best Martini: Next Steakhouse
Though red wine is the official drink to have with steak, the Martini definitely feels like ideal cocktail to start off the steakhouse experience. Sadly, most of the Martinis I sampled were enormous and boozy—a wicked combo that had me tipsy before the first course. I definitely prefer a more aromatic and balanced version, which doesn't have some vendetta against vermouth. That partly explains why I fell in love with the Martini served at the beginning of Next's Chicago Steakhouse menu. Instead of a glass of liquor and a drop of vermouth, Next goes with a 1-to-1 mix, resulting in a lighter and more enjoyable sip. Even though vodka was used instead of gin, I was so completely won over I had two. [Editor's Note: As a commenter pointed out, wine director John Schafer told Time Out Chicago it was shochu, not vodka. I'm not sure why I was told that it was vodka at the meal. Regardless, it was a great drink.]
Next Restaurant, 953 W Fulton Market, Chicago, IL 60607 (map); 312-226-0858
Best Dessert: Chicago Cut Steakhouse
This is kind of an extra, because I didn't order desserts at every single place. Honestly, how are you supposed to have any room in your stomach after eating a massive steak? But if you ever get the chance to try the pineapple upside-down cake at Chicago Cut, make sure to do so.
Chicago Cut Steakhouse, 300 N LaSalle Dr, Chicago, IL 60654 (map); 312-329-1800
This post may contain links to Amazon or other partners; your purchases via these links can benefit Serious Eats. Read more about our affiliate linking policy.