Chicago

You can have a little more fun in Chicago than in most any other city in the country, if you go about it right. It's not as big as New York nor as sophisticated as San Francisco, but it has a free-wheeling, fun-loving personality all its own that guarantees a good time to everyone. For the impromptu male visitor, it offers sights and entertainment in all sizes and shapes, including close to 249,000 unattached females betwixt the ages of 18 and 29 (and 18, let it be known, is the age of consent in Illinois).

If you come in by air -- pure jet service is available from both coasts, and prop-jet from Miami -- the first thing you'll spot is Lake Michigan, a shimmering blue-green playground in the summer. After you land at either Midway or O'Hare -- Chicago's two international airports -- why not pass the usual cab ride into the city and take a helicopter instead? You can make the trip in a scant 11 minutes and the whirlybird sets you down at Meigs Field, a lake-front air terminal just a taxi hop from the Midwest's most elegant showcase -- Michigan Avenue and the Magnificent Mile. It is magnificent, too, with some of the swankest shops in the world, as well as such lofty landmarks as Tribune Tower, the Wrigley Building and the Palmolive Building. Nearby, there's State Street and the Loop (named for the L tracks that encircle it), center of the city's vast financial and commercial enterprises, and all the other sights that you can learn about from any competent guidebook, which we suggest you pick up on arrival. Chicago, recently made a world seaport, is still the vital, throbbing City of the Big Shoulders that Carl Sandburg described 40 years ago. And while New York is surrounded by two polluted rivers, Chicago has 25 miles of lovely lake front -- lined with tree-shaded boulevards, gleaming skyscrapers (the world's first was constructed in this city in the late 19th Century), venerable mansions, handsome parks, a series of yacht harbors and a string of white sand beaches -- all right in its own front yard. Chicago also has its Near North Side -- part Greenwich Village, part Madison Avenue -- studded with nightspots that swing till nearly dawn.

You'll want to freshen up at your hotel before going out on the town. We assume you've made your reservations well in advance, a good idea when visiting any city, but especially Chicago, because it is the country's biggest convention town and accommodations aren't always easy to come by. The big hotels in and around the Loop -- the Palmer House, the Conrad Hilton, the Sheraton, the Pick-Congress, the Sherman, the Morrison, the Sheraton-Blackstone -- are right in the center of things. They all offer a number of first-rate bars and restaurants and if you like a lot of activity, hustle and bustle, then one of these is for you. If you're coming to Chicago for the Playboy Jazz Festival on August 7, 8 and 9, best stay at the Sherman, which is official Jazz Festival headquarters. There'll be transportation directly to and from the Stadium for all five concert performances, plus a jazz film, symposium and exhibit at the hotel. Most of the musicians will be staying there and the Sherman will be holding special Playboy parties each evening for the jazz stars, celebrities and those staying at the hotel. Singles begin at $7.45, doubles (continued on page 100) Chicago (continued from page 59) at $11.45, and there will be special dormitory accommodations available during the Festival for four at $12 per night.

Should you prefer a somewhat quieter, more elegant retreat, then you'll choose a place just outside the Loop, or on the Near North Side. Our first choice would be the Ambassadors, West and East, the latter being the home of the world-famous Pump Room, and both are handy to the Near North's main stem, Rush Street, where most of the late-night fun is to be had. The Ambassador is a hotel in the grand manner, invariably the stopping spot for visiting royalty and other dignitaries from around the world. You can rough it there in a $15 single room, or feel that you're spending your time at Buckingham Palace in a $140-a-day two-bedroom apartment complete with bar and outdoor patio.

If the Ambassador isn't your cup of tea, then we recommend Executive House, a newish and nifty modern structure on Wacker Drive that's furnished in best-of-taste Swedish woods and overlooks the Chicago River, the city's main commercial waterway and one that runs backwards (the natural current was reversed at the turn of the century, so that the river now flows out of Lake Michigan instead of emptying into it) right through the center of town. There is an excellent restaurant and cocktail lounge open on the first floor, and, as of press time, plans call for a sumptuous eatery in the penthouse. Your diggings at Executive House will run you anywhere from $12 to $85 a day. The Drake, our third recommendation, is in the tradition of the Ambassador -- quiet, elegant, loaded with expensive shops, fun bars and excellent restaurants (more about them later) and with a commanding view of the Outer Drive and the lake. The tariff runs from $9 to $85 a day.

As in other major cities across the U.S., the motel-in-town has made inroads in Chicago, too, and if you like sun patios, swimming pools, plenty of privacy and a chance to keep your car handy, we recommend the Sands Motel out north, the Lake Tower Motel midtown, or the 50th-on-the-Lake Motel on the south side.

Now for companionship. The secret of finding a pleasant, affable partner for the evening is a simple one, and one that doesn't apply to Chicago alone: start looking early in the day. Chicago's smarter shops, broad streets and pleasant beaches offer innumerable opportunities for the poor confused visitor to ask directions, and then take it from there. We have also audited some great boy-meets-girl success stories in the Art Institute, the Chicago Public Library, the Museum of Science and Industry, the Shedd Aquarium and the romantically dark Adler Planetarium -- Chicago is happily loaded with such shrines to the arts and sciences, and you can find them in your guidebook.

Should an early start prove impossible for one reason or another, there are several pubs and bistros around town that get a pretty good play from unattached young ladies during the cocktail hour. Generally, though, these more direct forays on the part of the girls are made in teams of two and three, and it isn't always a simple matter to cut one out from the herd. So take a buddy along while casing these establishments.

If it's a weeknight, and your taste runs to girls employed in the communications dodge, you can find sweet swarms of them in such watering holes as the Recess, the London House bar and the Top of the Rock; the last offers a stunning view of the city, being 41 stories above street level. Fashion models, airline stewardesses, secretaries and just girls favor the Scotch Mist, Easy Street, Le Bistro and Pigalle with their unescorted presence at the end of the day, drawn by the intimate and informal surroundings of these chic Near North clubs that not long ago were coach houses and garages; all serve sophisticated piano with their cocktails. Dante's Inferno offers devilish decor and a drink called the Diablo; Larry's, Gus' and the Dunes offer almost no decor at all, but are popular with the wenches just the same. Figaro's, on the beatnik side, has bizarre paintings on walls and ceilings, and a jukebox featuring cool jazz. The East Inn is a popular hangout with the college crowd and nurses who work at hospitals in the area; it's an unusual evening that doesn't find a dozen or so free damsels on the premises, and the Friday-night dances in the rathskeller (to an r-'n'-r jukebox) bring them out by the score.

If airline stews are your specialty, you'll find that a lot of them live in, and frequent the bar of, the Flamingo Hotel on the south side. That hotel and others out that way are thoughtful enough to keep a "Stewardess Register" on a table in the lobby, so it's possible for enterprising young chaps to leaf through and discover what stew from what city is in what room. How this information can be put to good use on the house phone, we leave to your imagination.

Once you've gathered up a date, you can either stay put for further cocktails at the places we've already mentioned or move on to some other worthwhile watering spots. The hotel beat rates your attention here: the quiet and relaxed atmosphere of the English Room in the Pearson Hotel, the air of unbridled excitement that surrounds the doings at the bar of the Pump Room in the Ambassador, the Coq d'Or in the Drake; or there's the Glass Hat of the Pick-Congress or the magnificent view from the Tip Top Tap in the Allerton. Cocktails at the sidewalk café at Riccardo's can be a special sort of treat in Chicago, which boasts few outdoor facilities for the inner man.

Most of the bistros in town offer patrons a dice game called "26" which is almost unknown outside the Chicago area. You get 10 dice and a cup and the idea is to make your point (any number from one to six) 26 or more times in 13 rolls. The house pays off in drink checks only, which keeps everything legal in the eyes of the authorities: 26 to 32 points pays 4 to 1, 33 and over pays 8 to 1; 13 points pays 2 to 1, 11 or less pays 4 to 1. If you get confused, the pretty creature behind the dice table will be glad to spell it out; incidentally, it's usually easier to make 26 than the 26 girl, who is so used to being pitched (nearly every guy who plays the game tries), she learned to say no long ago. Of course, there's always the exception, and it might be you (she's got to go home with someone, hasn't she?).

When your thirst has been assuaged, and you're ready to settle down to the pleasures of dining, you will be happy to know that there is no shortage of excellent restaurants in Chicago. But, by the same token, there is also no shortage of second-rate establishments that masquerade behind a giant menu or splashy decor. Space limitations forbid our warning you away from these latter joints, but those that follow we can recommend.

Chicago's grand luxe establishments include the Red Carpet, and they weren't whistling Dixie when they chose the name -- it's red-carpet service all the way by the most solicitous set of waiters in town. Small (seats only 42), the R.C. is fine for the candlelight-and-wine treatment in an intimate atmosphere. The menu is brief and elegant, featuring mostly French (the Châteaubriand with béarnaise is superb) and West Indian (ditto the Haitian lobster sauté) cuisine. The dining room is open till midnight, the bar till two; maître de's name is Jim. Another lavish and lovely dining facility is the Imperial House, featuring exquisite Continental fare such as whole pheasant en cocotte au beurre noisette capped with beignets de fraises with sauce sabayon. Excellent wine cellar; open for lunch, dinner, till 2 A.M.

Expensive but not unreasonable is the Cafe de Paris ($35 should do nicely for two, wine included), featuring good service and outstanding food; specialties are tournedos Rossini and duckling à la Belasco, a famed treat at the Cafe for more than 15 years. Maître de is Johnny; open every day from 5 till midnight. One of the newest, and best, of the top-level establishments is Maison Lafite, featuring an outsize menu loaded with Gallic delights, an excellent wine list, and a pianist who unobtrusively plinks away outside the dining room. Specialties include a sumptuous chicken Kiev, whose only sauce is butter sealed inside the breast, and tenderloin tips sautéed in wine. There's a bar adjoining. Maître de is Jerry; open 5 P.M. to 1 A.M.

Other grand luxe establishments you'll want to visit include the Cafe Bonaparte in the Sheraton-Blackstone, featuring French cuisine in the tradition of Napoleon's chef, Carême. There's dancing, too, after 9:30. Sasha's, a newish restaurant, is a fun spot serving up exotic dishes to the tune of strolling musicians. There's a "gourmet's choice" that changes daily, according to what Alexander "Sasha" Vereschagin has a taste for. It could be chicken veronica, chicken Kiev, bouillabaisse, or what have you, but all of it is a delight to the palate. Sasha's is tiny, too, so make your reservation early. Open from 5 P.M. to 2 A.M. daily. The Camellia House, in the Drake, is a spacious, well-appointed room that serves delicious food, notably the Monday-night gourmet menus (prix fixe of $9.50). There's a different feast each week, and the various dishes harmonize beautifully, with wine included. Other nights, the standard menu features such pleasures as pheasant Lucullus and roast squab Moscovite. Frank is the maître de; open till 2 A.M. Friday and Saturday, 1 A.M. the rest of the week; dancing and cabaret attractions.

Famed in legend and song is the Pump Room of the Ambassador East, celebrity showcase extraordinaire and purveyor of exciting food as well. The Pump remains the place in Chicago, and any young lady will love to be seen there. Open from noon to 2 A.M. If you don't care for the pomp at the Pump, you'll enjoy the more sedate atmosphere of the Buttery (with dancing) and the Beau Nash Club (blessed quiet), both in the Ambassador West; the menus in both are similar to the Pump Room's.

If Far Eastern atmosphere -- some of it corny but all of it fun -- is your dish, along with good food as well, we think you'll like the Cantonese cuisine and sunken garden backdrop of Shangri-La, the South Seas decor of Don the Beachcomber, the Polynesian hoop-la of the Traders, under the supervision of Trader Vic's in San Francisco, and the Polynesian Room of the Edgewater Beach Hotel, if you happen to be on the far north side. Dancing is available in the latter establishment, and all of the places specialize in outlandishly titled rum drinks (the vicious virgin, missionary's downfall, etc.) calculated to make the girls giddy.

Chicago abounds in other notable ethnic eateries, including the best in German food at the Red Star Inn, served up in unpretentious Old World surroundings at reasonable prices. There are 66 entrees on the menu, most notable of which are the Zwiebelfleisch au gratin and stuffed young goose. The Golden Ox also does wonderful things with German cuisine. For Hungarian fare, the Epicurean draws classical musicians and artists, is run by a retired ballet dancer, male, who bills himself as the Strudel King. Chicken paprikash, goulashes of all types, fruit pancakes and, of course, the strudel, are the highlights of the menu. Pasta addicts will want to try El Bianco, a moderately-priced Italian restaurant serving excellent grub and wheeling around an all-you-can-eat cheese and antipasto cart. If you don't want to travel that far (it's on the southwest side), try Riccardo's, La Scala (with private booths for the serious-minded) or Granato's to take care of your appetite. Pizzerias Uno and Due serve the most succulent pies in town.

Fanciers of Japanese cuisine will find the Azuma House completely delightful down the line, from food, to service, to surroundings. Should you want to go all the way, there's a special room for dining shoeless, seated on cushions at low tables. Gracious Japanese dining is re-created in the old style: sukiyaki is prepared at the table, and is a specialty, along with abalone yoshino-age, lobster curry-yaki and tempura. Lovers of Swedish smorgasbord can do no better than Kungsholm, an elegantly-appointed restaurant with one of the best smorgasbord tables in the country. Before or after your dinner, you may watch the nightly puppet opera. Greek cuisine is (no surprise) the specialty at the Athens, adorned with statuary of all the deities from Zeus to Pallas Athena, and serving inexpensive, tempting dishes -- lamb shishkebab, avgolemono soup, baklaya for dessert, topped off with an ouzo on the rocks. Try the Pantheon, across the street, for some frantic Greco-style entertainment. There's a small, undistinguished-looking Mexican restaurant that rates a stop: Cafe Azteca, complete with posters on the walls, guitar-strumming proprietor, and patio service in warm weather. No liquor license here, but you can bring your own bottles in with you. Or try stopping for your cocktails across the street at the Old Town Ale House, a beatnik, chessboard sanctuary for those who want to mutter about tourists. The Scheherazade specializes in Middle Eastern dishes in an Arabian setting, with reasonable prices and tempting entrees. Chez Paul, Jacques (with courtyard dining in the summer) and L'Aiglon are worth your while if you enjoy French cuisine, with the latter offering more than 400 dishes to select from.

Chicago, as you might have guessed, boasts some of the best steak houses in the U.S.A., featuring prime beef direct from the Chicago Stock Yards. Top position goes to two places, the Sirloin Room at the Stock Yard Inn, which features a "steak throne" where the customer chooses his own cut of beef and slaps his "brand" on it, after which it is whisked away to be done to a T; open daily from 11 A.M. to 11 P.M. Sharing top honors is an unreconstructed speak-easy-type eatery called Club Gene and Georgetti, featuring an à la carte menu and memorable steaks served with excellent cottage fried potatoes; stays open till 2 A.M. Other outstanding establishments for top-quality beef are the Porterhouse at the Hotel Sherman, Miller's Steak House (far north), Al Farber's Steak Room, Morton's Steak House (on the south side), the Corona Cafe, the Erie Cafe, the Brass Bull in the Sheraton Hotel, the Steak House in the Conrad Hilton and George Diamond's.

For prime rib of beef, you can do no better than the Embers (there are two of them, one on Dearborn Street, the other on Walton) serving great slabs of blushing, marbled meat at least an inch thick. Other prime rib houses worth your time include Don Roth's Blackhawk, the Cart in the Harrison Hotel, and Isbell's on Rush Street.

Seafood fanciers in Chicago have an excellent choice of restaurants. Leading the rest is the Drake's Cape Cod Room, a rustic, fish-netted cove serving delicious portions of their specialties: red snapper soup with sherry, French turbot, pompano sauté meuniere and Louisiana shrimps. The maître de is Eddie, the service is good, and the hours are 12 noon to 12 midnight seven days a week. The Well of the Sea, in the Sherman, boasts an imaginative subaquatic decor: the table lights are lucite jellyfish, the fluorescent wall murals are of highly unlikely sea denizens and the menu is imaginative and interchangeable with that of the Porterhouse, right next door.

Dinner, dancing and a full-blown nightclub show are offered by the Chez Paree, the Empire Room (in the Palmer House) and the Boulevard Room (in the Conrad Hilton). The Boulevard specializes in ice shows, if you care for that sort of thing, and the Chez usually offers the biggest name talent in town: Sammy Davis, Jr., Tony Martin, Jerry Lewis, Nat "King" Cole, Louis Prima and Keely Smith are regular headliners.

If you want a less pretentious show, you'll enjoy one of the smaller clubs: Mister Kelly's, the Black Orchid or the Cloister, all on the Near North Side. Kelly's and the Cloister offer hip comics (Mort Sahl, Lennie Bruce, Mike and Elaine) and singers (June Christy, Ella Fitzgerald, Anita O'Day); the show at the Orchid is a little more varied, from Frances Faye to Jack E. Leonard to Lily St. Cyr. Both Mister Kelly's (Dick Marx and Johnny Frigo Monday and Tuesday nights, the Marty Rubenstein Trio the rest of the week) and the Cloister (Ramsey Lewis Trio) have exceptional house combos playing the intermissions; Kelly's and the Orchid offer food with the program, but it's strictly a booze scene at the Cloister. Like it says in their ad, the Cloister swings till 4 A.M., and it's one of the friendliest clubs in town. The Junior Room of the Black Orchid also comes alive around midnight and goes till 4 with the swinging of Duke Hazzlit (who does Sinatra down to the last note and gesture) or Buddy Greco (who is too much just doing himself).

You won't want to miss Chicago's famous Gaslight Club, if you can find someone who has a key (it has a lock on the door, which makes it seem private, and brings in more business than if it were left wide open). This turn-of-the-century oasis features buxom waitresses, lightly clad, and lots of singing round the piano; it has proved so popular with ad executives and clients (an ad man started it) that they now have branches in New York and Washington, D.C.

For jazz in the Windy City, your choices are many and good. Modern jazz addicts dig the sounds at the Blue Note, which offers everything from big-band jazz (Kenton, Basie, Ellington) to combos and vocal groups (the MJQ, Gerry Mulligan, Dave Brubeck, and Lambert, Hendricks and Ross). Though the place isn't long on atmosphere, no self-respecting jazzophile who wants his passport renewed would miss the Note on a Chicago junket. Other full-time cool spots are the Preview Lounge in the Loop, and the Sutherland Lounge on the south side. The London House often features small jazz groups along with a tasty charcoaled menu.

Dixieland devotees will find Jazz, Ltd. to their liking. It's a ground-floor, smallish room dedicated to the kind of music that made Chicago famous. Equally boisterous are the Cafe Continental, where Bob Scobey's Frisco Band is currently holding forth, and the Club Bambu right around the corner.

If folk singing moves you, check in at the Gate of Horn; you might find the College of Complexes to your liking, too, with everything from folk singing to impromptu lectures in defense and damnation of practically any subject under the sun. It's a younger crowd that hangs its hat here and the principal beverage consumed is beer. Same goes for the Ivanhoe, with a below-ground labyrinth of bars called the Catacombs, plenty of pianos for community singing and many of the trappings of a fun house at an amusement park. Or if it's a real amusement park you want, Chicago's Riverview is one of the biggest and best in the country: roller coasters, parachute jump, cotton candy, and scads of unescorted quail just waiting to be taken for a ride. If sports hold any interest, Chicago is a big sports center, with top baseball, football and hockey teams and a number of important fights at the Stadium during the year.

You can sometimes catch an unusual show out at Roberts Show Club on the south side (the Jewel Box Review, blue comic Redd Foxx, or top talent like Dinah Washington or Lionel Hampton). If the slightly risqué is to your liking, you may get a kick out of Phil Tucker, who has been titillating Chicagoans with his particular brand of wit for longer than we can remember. You'll find him at the Silver Cloud.

Strip shows aren't what they used to be in Chicago. The heat is on all over town and even the best at the Silver Frolics is only a shadow of its former self. It's a different matter in suburban Cicero, however. Just 10 minutes from the Loop, at the Frolics, on 22nd Street, the girls peel off everything down to, and including, the G-string. Things were wide open in Calumet City (just over the Indiana border, half an hour from the Loop), too, till a Federal Grand Jury cracked down on its "street of sin" a while back. Folks feel that Cal City might be a wicked influence on sailors from all over the world who come to Chicago via the St. Lawrence Seaway, but attempts to close Cal City down have been tried before and failed, so it is difficult to tell at press time how much success this one will have.

Callgirls aren't as common in Chicago as they once were, either, but they can still be found on occasion along La Salle, Clark and Wells streets, and the south end of Wabash. Prices range from $10 on up. A number of motorized maidens in the Loop area operate out of late-model cars, but when business gets slow, they're apt to join their sisters on the sidewalk. Houses are practically non-existent in Chicago, and those that do open are soon raided, forcing the girls to move elsewhere. Most of the town's hot pillow trade is transacted by telephone, with the numbers widely circulated amongst bellboys, bartenders, cab drivers and other public servitors.

Chicago is a stay-up-late city; all places serving liquor are allowed to stay open till 2 A.M., and those with special licenses, till 4 A.M. on weeknights and an hour later on Saturdays. If hunger has returned, Julian's, at Chicago and Rush, is open all night, and the Trade-winds, at Rush and Delaware, offers food until 6 in the morning, and serves as an early-morning gathering spot for celebrities in town and for off-duty waitresses from the just-shuttered Near North clubs. If you're still not ready to call it a day, the Clark Theatre offers a different double feature every day with the last complete show starting at 4 A.M. Or if you're in a romantic mood, take a walk along Oak Street Beach and watch the sun come up over Lake Michigan. It's a sight you'll never forget.

As you will have gathered by now, Chicago is a scene you'll be glad you made. Like they say in the song, you'll have the time, the time of your life, for it really is a toddlin' town.

For the visitor to Chicago flying his own plane, Meigs Field on the lake front (top) offers easy access to the heart of the city, whose brilliant night skyline shines in welcoming beauty. Meigs also provides direct helicopter service to and from the breezy burg's two international airports, Midway and O'Hare.

Above, Riccardo's sidewalk café and restaurant features a near-Neapolitan atmosphere, complete with outdoor cocktails, opera-spouting waiters and exhibitions of contemporary art.

Right, the lights and sounds of the city after dark are apparent strolling north on Rush Street, nexus for much of the night life on Chicago's glittering Near North Side.

Left, sophisticated folk gather round the piano bar at the Scotch Mist.

Above, smart jazz sounds combined with charcoaled fare are the attractions at the London House.

Below, portraits of buxom, bygone broads, waitresses in scanty attire and mustachioed bar-keeps are fixtures at the famous Gaslight, a key club dedicated to the frolicsome fun of the Gay 90s, popular with the ad exec crowd.

For savory supping, Chicago boasts a varied line-up of restaurants. Top left is the near-ultimate in poshness: the Pump Room of the Ambassador East Hotel, invariably a stopping place for celebrities because of the quality of its menu, service and decor.

Left, specializing in superlative smorgasbord, the Kungsholm draws the gourmet, also boasts a midget opera house, where expertly manipulated puppets do pantomime to stereophonic opera recordings.

Above, the exotically Far Eastern Shangri-La, a romantic rendezvous serving Cantonese delicacies and a heady assortment of stimulating, rum-based drinks.

Show time in Chicago, and the big, brash nightspots and intime clubs all come alive. Top, the venerable Chez Paree, must-see mecca for the town's visiting firemen and showplace for headliners in the entertainment biz; here, the Adorables strut and sing, to be followed by the likes of Sammy Davis, Jr., Jerry Lewis or Louis Prima and Keely Smith.

Above, the Black Orchid, a supper club whose entertainment policy runs the gamut from undulating ecdysiast Lili St. Cyr to crooner Johnny Mathis.

Below, the subterranean Cloister introduced sick comic Lenny Bruce to Chicago, usually couples hip humor with swinging singers like Anita O'Day.

Entertainment for every taste can be found in or near the Windy City. Top left, the low-lit Gate of Horn spotlights folk singers such as Josh White.

Center left, epidermis displays are featured at the strip joints in nearby Cicero and Calumet City, where the action lives up to even the wildest of expectations.

Bottom left, nuzzling and guzzling are predominant at the East Inn, a boy-meets-girl hangout for collegiates and nubile nurses from nearby hospitals.

Top right, le jazz cool can be sampled at the city's most famous jazz joint, the Blue Note in the Loop, which consistently features top groups like the Gerry Mulligan Quartet.

Bottom right, the south side scene at the Sutherland Hotel Lounge, where the Max Roach Quintet and similar combos hold forth.

Left, a topper for any evening on the toddlin' town is the magnificent panorama afforded by the window-side tables of the Tip Top Tap atop the Allerton.

Above, Chicago's lake-front scene is as beautiful a sight as any city in the U.S. has to offer, and a sunrise stroll along the shores of Lake Michigan can provide a romantic last memory for your visit.