Editor's Note: Whether you're a tourist or an office worker in downtown Chicago, you can get sick of eating at chain restaurants all day. So we've started a series to get you the lowdown on where to find a great and affordable lunch.

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[Photographs: Dennis Lee]

After ten months of being without a full-time job, I finally landed a gig. And it feels marvelous. Nobody ever tells you about how boring and lonely being unemployed is; I always thought I'd be happy just bumming around, but it turns out the rest of the world has jobs during the day, so you end up watching a LOT of The Price is Right with your cat for company. What's even better is that I was also able to land a job in a really fun industry, too. (Hint: It goes in your face, and you're here on this site reading about it right now.) And by the way, this is a big career change for me, so if you're in the same boat and you're waiting to take a chance, there's no time like the present. Writing for Serious Eats as a contributor was what really made it happen, and the fact that you guys still read anything I write has made a huge difference in my life in ways you might never fully know.

For this week's Lunch in the Loop, I wandered into Rudy's Bar & Grille, right by Michigan Avenue on Madison. I love Lunch in the Loop because I always end up looking like a lost Korean tourist. I have a camera bag, I'm perpetually confused, and I point at pretty much everything I look at. Rudy's just so happens to be next door to Pizano's, and that's no coincidence: Pizano's is their sister restaurant. And as soon as I opened the menu, I immediately turned into Curious George. They proudly state that they are the home of the "Famous Milkshake Martini," and they have a food eating challenge. I knew I was in for a true treat.

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I'm not much of a day drinker, but as soon as I saw the milkshake martini, nothing was going to stop me from having one. Nothing. The friendly and cheerful waitress suggested I try the Peaches and Cream milkshake martini ($10.50). For some reason I expected a watery, milky drink, but the milkshake martini is a serious milkshake with some serious booze in it. It's delicious, and best of all, it's fun as hell. No kidding.

Sure, it's flavored with peach schnapps and not actual fruit, but in this case, the schnapps tastes like peach-flavored candy and pairs well with vanilla ice cream. If I had to liken it to anything many of you have tried, it's like a Steak 'n Shake milkshake with some adult juice poured into it. Plus, I made a sacrifice for you guys, since I'm lactose intolerant. My poor roommate.

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The pretzel bun grilled cheese ($8.95) is a great idea and I'm actually wondering why I haven't seen it more often. They wisely split the bun, invert it so that the crust becomes the center, and griddle it until golden and melty. The only other time I've seen this technique is on a Luther Burger—the burger with the glazed donut bun named after my favorite singer (just kidding... or am I?), Luther Vandross. Rest in peace, Luther. The reason why this sandwich is successful is because the pretzel flavor remains deliciously intact on the inside, and it's also easier to handle. In the end, it's just a grilled cheese, but it's different enough to make it interesting.

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I'm a sucker for patty melts, and I had to order it from the "famous burger" portion of the menu. The patty melt ($12.50, add $1 for waffle fries) is served on dark rye, and is exactly what you'd expect, with plenty of melted cheese and grilled onions. Unfortunately, the beef came out slightly overcooked, and as a result, it became dry, with very little telltale juiciness left on the plate. If you're in the mood for fries, spring for the waffle fries, they're crispier than the limp regular ones you get by default.

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As I scanned the menu, a particular item in the corner caught my eye. It's called the Chicago Char-Grilled Salad ($11.50), and suddenly, I had flashbacks to Lloyd's (review here), where I ordered a salad with a hot hamburger patty on top, which was pretty much a train wreck. But as the eternal optimist, I had to order it in the hopes that a culinary miracle would occur. Even the waitress hesitated to write my request down on her ticket.

It starts with chopped mixed greens, tomatoes, red onions, pickle slices, diced American cheese, and your choice of a hamburger or a hot dog. It's garnished with pretzel croutons and onion rings, and tossed in a "special dressing." Since I've never had a hot dog on a salad, I totally had to have one. Now, I'm absolutely shocked by this, but it's...actually good! I know the description makes it sound like the definition of a bad idea, but I could not stop eating it. The secret dressing is nothing more than ketchup, which sounds like an even worse idea, but it's somehow perfect. Each bite is a mix of crisp cool lettuce, sharp onion, rich encased forcemeat, sour pickle, and crunchy toasted pretzel croutons, along with, well, sweet ketchup.

You obviously have to enjoy ketchup, but if you think about it, most of these components are found in a Chicago-style hot dog. Before you bitch about the ketchup, mustard would have been a terrible choice of dressing, as it's just not sweet enough to seal the deal. Each forkful tastes like the salad version of our favorite hometown wiener.

As someone who's been lurching through the Loop trying to find surprises and things for you to enjoy, Rudy's has shown me that, even when all of your hope is nearly gone, the impossible can be achieved. Just like gaining a job after being unemployed for what feels like forever. More importantly, there's hope for things in this world like impossibly delicious hot dog salads that you can wash down with a milkshake martini.

About the author: After a failed attempt at starting a chain of theme restaurants called "Smellen Keller," Dennis Lee traveled the world to discover his true passion. Sadly, midwifery didn't pan out. Now he works in a cubicle, and screws around as much as possible. Follow his shenanigans on Twitter.

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