The first Chicago guidebook I ever read was written by a New Yorker.

A gift from my father before I started college in Hyde Park, Mr. Cheap’s Chicago by Mark Waldstein (1994) had a cover that promised “Bargains, factory outlets, off-price stores, deep discount stores, cheap eats, cheap places to stay, and cheap fun things to do.” To a newly arrived 18-year-old on a very limited budget, it seemed like a cornucopia of truly marvelous delights: freshly browned biscuits from the Valois Restaurant, $2 movies at the Talman Home Savings Bank theater, and most curiously, a theatrical extravaganza at the Neo-Futurist Theater called Too Much Light Makes the Baby Go Blind.

Outside of a brief bio of Waldstein on the back of the book (“a writer, actor and ‘starving artist'”), there were no clues to exactly what possessed him to create this 320-page guide to nightlife, flea markets, delis, discount record stores, and used clothing outlets in and around Chicago. But it certainly seemed like it was written just for me, with its careful eye for detail, informal style, and the eminently approachable manner in which it described Wicker Park, Maxwell Street, and West Rogers Park. I didn’t know anything about these places, yet Waldstein began to fill in my own mental map of the city by telling me about Moti Mahal Restaurant on Devon, Mort Cooper’s men’s clothing store in the Loop, and the Carpet Market in Wicker Park. Somehow the thought of a massive warehouse with Berber rugs at $4.99 a square foot struck me as quite urbane.

It was the start of a long obsession with Chicago guidebooks from the recent and not-so-recent past that continues to this day.

One of my next discoveries was Isabella Bird’s An Englishwoman in America. Published in 1856, the book covers Bird’s travels around the United States and Canada a few years prior. Looking through the table of contents, I breezed by the chapter subheadings “The hickory stick,” “Hard and soft shells,” and “Nocturnal detention.” My eyelids began to drop and then I glimpsed the windiest one of all: “A Chicago hotel, its inmates and its horrors.”

Reader, I read on.

Bird had just arrived from Rock Island via train and had attempted to find lodgings at one of Chicago’s “two best hotels.” She graciously omits their names and finds herself at a low-cost lodging “the name of which it is unnecessary to give.”

A policy of anonymity is perhaps best in this case, as Bird feels ill upon the sight of a room with barely any natural light and a “dirty- buffalo skin,” which, as it turns out, is an informal hotel to a raft of filthy vermin.

This is merely an amuse-bouche for what follows: “We went down to dinner and only the fact of not having tasted food for many hours could have made me touch it in such a room.”

Her review of this culinary tableau continues: “There were eight boiled legs of mutton, near raw; six antiquated fowls, whose legs were of the consistence of guitar-strings; baked pork with ‘onion fixings,’ the meat swimming in grease.”

It was clearly not a pleasant repast, yet I do believe this passage should be counted as the first full-fledged review of a restaurant in Chicago. It ranges beyond food to complete this most rustic portrait with commentary on Bird’s dining companions and their manners.

Over time, authors of Chicago guidebooks began to look around and describe various neighborhoods, institutions, transportation, higher education, and perhaps most importantly, the progress of development that made Chicago Chicago. Chicago and Suburbs, a companion to the 1939 WPA Guide to Illinois, includes a rousing look at the city close to its industrial peak.

I recall being most impressed by the jaunty narrative essay that opens the Chicago chapter: “Chicago, vibrant, noisy, every inch alive, is the youngest of the world’s great cities, and has the optimism, the exuberant and often rather self-assertive pride of youth.” If I wasn’t already reading these words while already in Chicago (albeit inside a brutal concrete tomb of a library), I would have jumped on a plane or hopped a train immediately to interrogate this claim.

What I continue to find so wonderfully engaging about this guidebook is the walking tours through the Loop, the near north and west sides, and other communities. As you turn each page, perhaps as you are holding the book in hand, you may feel that sense of the past as present, comparing and contrasting as you make your way pass the former “Death Corner” at Oak Street and Cleveland Avenue, which was “the scene of more slayings during the Prohibition era than any other point in the city.” A morbid thought, yet somehow just another one of Chicago’s endless well of superlatives, ranging from the sublime to supercilious.

What was the world of Chicago nightlife like before Yelp, TripAdvisor, and other sites proffering suggestions from folks like “MalortFace4U” and “RushStreetNightz”? One could ask friends, one could ask a concierge, and one could certainly flip through a copy of Dr. Night Life’s Chicago (1979) by the Tribune‘s Rick Kogan.

I first discovered this book at Powell’s on 57th Street, and I remember seeing an introduction by Mike Royko that referred to Chicago as “one of the great drinking towns of the world.” Ah, another superlative for the Windy City. As I had recently turned 21, I was curious to see whether this book would afford me a catalog of places where one could join others for a tipple.

The guidebook covered a wide range of drinking establishments, divided into thematic chapters like “Institutions,” “The Swinger,” and “Still Crazy.” As I made my way through the entries, Kogan’s tone felt like talking to a friend you’d met on the el and moments later, there you were at the Wrigley Building Bar (RIP) where “the activity is so lively that it looks like they are giving away booze.”

Kogan says now that the Dr. Night Life persona was “a weak homage to Mike Royko’s Slats Grobnik, conceived one night at Riccardo’s with newsman Mike Flannery. Originally we thought ‘The Reverend Dr. Night Life,’ but clearer heads prevailed the next morning.”

I might also mention that each watering hole reviewed in the book receives zero to five shot glasses as a type of overall grade. The Billy Goat and the Pump Room (as operated by Lettuce Entertain You) both receive a relatively rare five-shot-glass review. Looking back now, Kogan says O’Rourke’s, Wise Fools Pub, Bistro, Faces, Billy Goat, and Theresa’s Lounge were places that really captured the spirit of nightlife in the late 70s. But there’s no going back:

“Taverns are of their time and place,” he says, “and the best of them have always operated as homes away from home. The great piano bar genius Buddy Charles once told me that people go to taverns because they are eager for intimacy.”

Kogan’s observation is something that resonates with me as I think about these guidebooks. They are also very much products of their own time and place, offering a modest glimpse into attitudes about nightlife, dining out, architecture, and in some cases even the cadence and structure of a single block.

I also can’t help think that in our own time, with websites and social media sites proffering up endless pieces of windy advice, there’s something rather refreshing about the finite quality of guidebooks. I find it most welcome to unplug for a bit, take one out, make some notes along the way, and give myself time to wonder.   v