Building an Eating Itinerary: Chicago as a Case Study

My stomach and I were glad to be in Chicago!

Hot Dog at Portillo's, moments after dropping luggage at the hotel. Snappy and surprisingly delicious.

After the hot dog, it was time for an Italian Beef Sandwich at Al's Beef. (This was pushing dangerously close to dinnertime.) While I enjoyed the giardiniera and sweet peppers (and loved how the sandwich is drenched in beef juice), I'd choose the hot dog over this sandwich.

Day one ended with a delicious tasting menu experience at the "Kitchen Counter" of the Storefront Company restaurant, which generously hosted dinner. One of my favorite courses: Scallop with Prosciutto Air, Rind Pickle, Walnut, and Oxalis Flower.

Before a morning tour of Wrigley Field, it was time for breakfast at Southport Grocery & Cafe. Here's the Grown-Up Pop Tart, with local fruit preserves, mascarpone, and vanilla walnuts. Nice cafe, though this dish was more fun than fantastic.

I've had a few Chicago-style deep dish pizzas in the past, so I was hesitant to allocate stomach space to this filling dish. Still, for the sake of this report, I visited Lou Malnati's Pizzeria to get the 6" Malnati Chicago Classic. Buttercrust, yes. Stomach-filling, yes. Do I still prefer NY-style pizza? Yes.

Crazy Squid (with bird chili, lemon balm, green garlic, and cashews) at Fat Rice, part of one of my favorite meals in Chicago. Great Macanese food!

Late-night churros under the moonlight at Xoco, along with an "Authentic" bean-to-cup hot chocolate.

First visit to Intelligentsia after drinking their coffee at home the past couple of years. With my pour-over: a delicious pistachio doughnut with Meyer lemon glaze from nearby Do-Rite Donuts.

Lunch at Publican Quality Meats included this Little Butcher Boy sandwich (cappicola, liverwurst, arugula, mustard girl spicy honey mustard, aioli, pickles, and balsamic dressing) and a kale salad. The ribollita soup was also amazing, making this another of favorite meals in Chicago.

Adjacent to Publican Quality Meats is Glazed & Infused, where I simply had to try (and enjoy) one of these Coffee-Glazed doughnuts.

Seafood stew at the charming Ruxbin.

Another day, and another round of coffee and doughnuts. Good brew from Bow Truss Coffee Roasters; Valrhona Chocolate with Espresso Cream and an Old-Fashioned smuggled in from Firecakes.

Hosted lunch at Sepia, which feels like an elegant place to take a client out for business. My Arctic char portion was rather meager, while this "Pinto Box" of cucumber gazpacho, pasta a la chitarra, and fresh and dried fruits seems rather small and expensive for $20. Well-executed food, but good thing we had a big meal ahead on the eating itinerary!

I loved Purple Pig so much during a previous visit to Chicago that I had to return. Sitting at the chef's counter is incredible fun, as you get to watch the controlled chaos. The food was delicious as always, including this Pork Secreto with Roasted Red Pepper, Leeks, and Pickled Watermelon Rind.

Croissants at Toni Patisserie (just so-so).

A return to Intelligentsia, this time with one of their own croissants. A doughnut would have been a better choice!

Blackbird offers a lunchtime prix fixe menu that's a value at $22. The food is a little fussy, though, and ultimately I prefer sister restaurant Publican Quality Meats to this white tablecloth affair. Desserts were the standout of the meal, included this Roasted Peanut Ice Cream with Carrot-Barley Sponge, Honey Mousse, Pickled Carrot, and Opal Basil.

For the airplane ride home, "The Beef" sandwich from Little Goat hit the spot with its kimchi, horseradish, bread & butter pickles, and "fat bread."

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“How do you decide where to go eat?”

This is the most common question I get, as someone who writes about restaurants. Notice I didn’t call myself a critic. A critic waits about a month to make a first visit to restaurant (though one can argue that a restaurant should be good on day one), visits at least three times to check for consistency and to ensure that the restaurant wasn’t having an off day (though one can argue that a restaurant should hit high marks all the time), and strives to be anonymous (though one can argue that every patron should be treated as a VIP). In contrast, I don’t always wait for a restaurant to work out the kinks, I typically only go once before writing, and I’m not always anonymous.

My writing has appeared in print and blogs, national and local. Just about everything gets cross-posted to my Gastrolust blog, where I add an image link for each restaurant so that the blog post gets aggregated to the restaurant’s page at Urbanspoon. (The process is known as “spoonbacking,” which sounds somewhat gastro-lusty.) As a (day-job) public speaker who is critiqued and must perform well to get paid in the future, I know the power of criticism and try to be sensitive to the impact my writing will have on a business. At the same time, I’m not afraid to report on what’s not going well at the restaurant.

The reason for my bluntness: a restaurant visit takes up my time, energy, stomach space, and money. Seattle is full of “Microsoft Millionaires.” I am not one of them. For most of my writing assignments, I don’t get reimbursed for my expenses. (And the pay is rather meager.) I am quite frugal, and while I’ve been lucky to enjoy some of the finest restaurants locally and beyond, on my own time and dime I’m typically cooking at home or eating modestly at a hole-in-the-wall noodle joint.

So when headed out to eat, what are some of my general considerations in choosing a place? Food comes first, as I’m looking for quality and/or uniqueness. Price is important, as I’m always aware of budget constraints. Service counts, but is a lesser concern. Same for setting and atmosphere. I’d much rather have good food thrown at me by a bad server in a dingy restaurant than mediocre food served with white gloves in a room with crystal chandeliers. (Alcohol, by the way, is not a factor for me, as my focus is on the food.)

Actually, I have one major concern regarding ambiance. I strongly prefer quiet restaurants to noisy ones. I often comment that one popular restaurant in Seattle is so loud that you can’t taste your food. If I’m not dining alone, I want to be able to talk with my companion(s) without screaming and straining to listen. A parched throat and exhausted ears and mind can override happy taste buds and stomach. Call me a curmudgeon, but the trend of noisy restaurants and restaurateurs who equate sound as liveliness does not suit me. So a place where I can enjoy quiet conversation and a peaceful meal is appealing. (That said, I do like to banter with the kitchen staff, and consider a counter seat at a chef’s station to be a meal and a show.)

With all of these considerations at play, how to I choose specific restaurants, especially when I’m traveling away from home? I’d like to offer up my recent trip to Chicago as a step-by-step case study.

1. Personally contact family and friends who know the location. I know very few people living in Chicago, and they didn’t offer help, which was unusual. Luckily, some friends who’ve traveled there in the past did send recommendations.
2. Post an inquiry to Facebook and Twitter. With about 2,500 friends and followers in my combined accounts, many of whom I don’t know (especially on Twitter), there’s good reach and I often get helpful responses. This can be more challenging on Twitter, with its 140 character limit, but posting might evolve into conversations or generate emails. For my Chicago research, my posts returned a lot of recommendations for better-known restaurants, and also a few eye-openers.
3. Check Serious Eats and Eater. Eater offers fairly up-to-date ideas, as there are “heat maps” and specific sites for many cities. The search function at Serious Eats can lead to some interesting posts and discussions. I don’t, though, browse too far back, as that can be overwhelming and yield results that are outdated. Serious Eats has strong Chicago content, so the site was particularly helpful for my trip planning. (If you search Seattle, you’ll see a lot of my writing at Serious Eats.)
4. Go to the Chowhound discussions (in the past, the eGullet forums were good, but that site seems less active) to take a scan of recent activity. As at Serious Eats, the search function helps here. And if a city is home to a local food message board, as Chicago has with the LTHForum.com, you can hit a goldmine. By now, restaurant names should start to get really familiar, so I start listing them out (yes, on paper, the old-fashioned way) as breakfast, lunch, dinner, or snack options.
5. Google a particular restaurant name and city. The search result usually yields Urbanspoon, Yelp, and Tripadvisor hits toward the top, where I can quickly scan numbers to see rankings and popularity, for what they’re worth. I usually click on the Urbanspoon link, as I like the site for its variety of critic, blogger, and individual reports, as well as its “Talk of the Town” and “Most Popular” sections. I ultimately ate at a few restaurants that are typically in Urbanspoon’s “Talk of the Town” section. As of this publication date, I went to at least one place in each of the three “Most Popular” lower-priced categories—and unsurprisingly didn’t go to any in the “Fine Dining” category.
6. Find a trustworthy blogger. There’s likely one whose writing will really resonate with your dining preferences. Via Chowhound, I “met” Uhockey. While we’ve never actually met in person, or even emailed each other, I believe we’ve commented on each other’s postings, and I’ve followed his advice in places like Paris. His exhaustive posts for Chicago helped me in making restaurant selections.
7. Check restaurants’ websites. They will usually be the top hit of the previously mentioned Google search. Once intrigued enough by a restaurant, I can get a feel for the restaurant’s “mission” and specific menu details at its website. (Hopefully. I dislike when restaurants don’t post current menus, and especially dislike when prices aren’t included. This is about the only time I’ll turn to Yelp, with hope of finding a photo of the current menu.) It was an older version of Fat Rice’s website that turned me on to the restaurant, with its casual yet strict dining “rules,” along with its photographs and descriptions of the food.
8. Post a question or two to Chowhound. Sometimes I’ll ask a specific question about a specific restaurant, or if I’m needing more, put out a general inquiry about the city if I can’t find the question already answered. Maybe I’ll even share my overall itinerary and ask for feedback, as I might learn that certain restaurants are more alike than I thought. I did this for Chicago and got helpful suggestions, and even created some healthy debate about best hot dogs. The key is to be as specific as possible with your inquiries. (And don’t forget to report back after your dining experiences!)

As a writer, one extra step I might take is to contact a public relations firm that represents a restaurant that interests me (or the tourism office for the city/region, especially if I’m traveling internationally). Usually I’ll contact PR firms if I’ve had contact with them previously in the course of my writing. They can help with information, photos, and more. Sometimes the firm offers to host a meal. Disclosure: I’ll sometimes take up the offer, but without promise to write about the restaurant, and certainly without obligation to praise it or to avoid writing something negative. I can tell you a dozen restaurants that wish they’d never hosted me for a meal! In Chicago, I had two hosted meals, one that I enjoyed considerably more than the other in regard to quality. (On a separate note, I also went to two restaurants owned by one restaurateur, and liked the lower-cost place more than the “fine dining” restaurant.)

Research completed, it’s time to build the eating itinerary. I’ll look at open hours and locations, then map out my choices to see what makes sense for breakfast, lunch, and dinner. I almost never take a taxi (did I mention my limited budget?), but am unafraid to tackle public transportation, which I embrace as a fun way to see a new city. I also like to walk, which burns a few of the calories and lets me get a closer look at some interesting neighborhoods.

And, yes, I’ll fill in the itinerary with some tourist activities—dictated, of course, by meal geography and time. (I especially enjoyed planning meals in Paris, filling in a blank map of the arrondissements and then figuring out what museums would fit between meals.) Some of those sites will be food markets, which allows for more noshing. In Chicago, I didn’t want doughnuts, pizza, hot dogs, and the like to take up coveted meal slots. So many of those iconic items became snacks between meals.

If it’s not yet obvious, I’m a voracious eater. During a recent trip to Vancouver, I visited 21 places in 72 hours—19 in Richmond, which I’ll report on soon. The food was a little heavier in Chicago, but I still managed to hit 20 places during my four-day stay. Check the slideshow above for a look at a bite from each place I visited.