It’s after 3 a.m. on a recent weekday and jazz vocalist Kimberly Gordon has a message for those slumbering toward another ho-hum Wednesday morning.
“To the people out there sleeping right now I say, `God bless ’em, but you’re missing a whole world of living,'” she yells over the clamor of a swinging jazz club.
Gordon is among more than 50 people packed into the Underground Wonder Bar, 10 E. Walton St., on what is normally a school night for most Chicagoans.
The lounge buzzes with the energy more typical of a Saturday night five blocks north on Division Street. All 17 stools encircling the front bar are occupied. In the distance, past dozens of bodies and through a smoky haze tinted red by Christmas lights over the bar, pianist Vince Willis jams a little jazz out of a piano on a small stage.
Best time in the city
“Between 2 and 4 a.m., this is the best time in the city,” said Wonder Bar regular Dealve Smith, who drives from the South Side to hit the Underground. “The rest of the world is asleep so there are no cars on the street. You always find parking and you’ll make every stoplight.”
It’s 3:30 a.m. now, and Underground patrons, many of whom either fell out of neighboring watering holes at 2 a.m. or just got off work at area hotels and restaurants, push into late-night Tuesday. Or is that early morning Wednesday?
“You see this is Tuesday night action,” said Smith, 51, looking at his watch. “Although it is past 3:30 Wednesday morning, tomorrow doesn’t officially start until everything slows down at 4 or you crawl into bed, whichever comes first.”
While most downtown residents recharge for another workday, a vastly different Chicago exists between 2 a.m. and dawn.
Unlike New York, Chicago sleeps, and soundly. Streets like LaSalle, Adams, Clark and Halsted become eerie in their 4 a.m. silence. As predicted, parking is a breeze and streetlights turn green almost magically, as if orchestrated for your car.
The Magnificent Mile is traversed in seconds; the LaSalle cavern sits motionless except for the rhythm of a set of rear blinkers on a double-parked delivery truck; Halsted snoozes but for the passing of a cab down Monroe Street.
Walking Oak Street, the hustle of shoppers and tourists, present hours earlier, has vanished. Trendy shops idle in darkness, and the bright, pulsing energy of the Esquire Theater marquee stands lifeless, unplugged.
When the party ends
After 4:30 a.m., even the rowdy late-night revelers retire. Now, laborers in the quiet backstage of pre-dawn spruce up and unload Chicago.
For pastry fans, Sal Prato might have the most tempting overnight job. He drives a delivery truck for Gonnella Baking Co., dropping off hundreds of loaves of breads and sugary delights to downtown hotels, restaurants and cafeterias.
As Prato’s truck pulls into the loading dock of Northwestern Memorial Hospital, the aroma of warm, freshly baked bread beckoned.
“You get used to the smell,” said the 20-plus-year veteran of the downtown route. “But no matter how many years I am on the job, I’ll never get tired of the food–I still love to eat baked goods.”
Three blocks west, union worker Don Jacobsen is anticipating the end of his shift. In his mind, there is no Tuesday night-Wednesday morning debate. It’s the start of his weekend, and he is thankful.
Jacobsen, 24, has about 100 more yards of sidewalk to power-wash around the Westin Hotel on the corner of Delaware Place and Michigan Avenue. Then, he’s got big plans.
The following day is the one-year anniversary of when he and his girlfriend started to date, and he is taking her to dinner atop the Hancock Center, which looms across Delaware encircled in fog.
“After I get off around 9:30 [a.m.], I’ll go home, get some sleep and come right back down for dinner up there on the 95th floor,” Jacobsen said. “These hours might be tough for a guy with a family, but for a young guy like me, I like them.”
A former bartender at Reilly’s Daughter in Oak Lawn, Jacobsen now stands shrouded in fine mist. Armed with a high-pressured water hose, he pushes yesterday’s dirt to the curb with a swoosh.
“Although the hotel is busy with people coming and going all night, this is the best time to get this kind of stuff done,” he explains. “The guests are high enough up so they can’t hear, and the sidewalks are pretty much empty this time of night.”
Keeping it clean
Two blocks south, Tony Flores is working on and under one of those sidewalks.
The father of five from Palatine is cutting large metal bars with an electric saw outside the main Michigan Avenue entrance to Water Tower Place. In the early morning darkness, he releases a shower of sparks with his saw. The bars will go under the sidewalk to support a planter for decorative trees that front the shopping center.
“With kids, the hours are hard sometimes,” Flores said. “Sometimes I don’t get to see them. They’re either asleep or off to school when I get home, … but I love my job no matter what time we work.”
About 10 blocks south, Streets and Sanitation laborer Betty Swanigan works the graveyard shift. The 42-year-old from the West Side finishes picking up trash around the Chicago Cultural Center and heads to the dump to unload her pickup truck.
The 10 p.m.-to-6:30 a.m. shift allows the mother of three and grandmother of a 2-month-old to baby-sit so her daughter can finish high school.
“Sure, I could do the 9-to-5 life, but I’d rather work nights,” Swanigan said. “I get to see some great sunrises out here, and most importantly I can spend more time with my kids.”
Dawn rolls in
As dawn approaches the city begins to perk.
Around the running track in Lake Shore Park at Chicago Avenue and inner Lake Shore Drive, a half dozen early morning walkers and joggers begin to circle the oval.
Across Lake Shore Drive, the pace on the bike path quickens. Only an hour before, it took 10 minutes before someone passed. Now a steady stream of heavy-breathing exercisers run, bike and blade the lakefront.
Sarah Johnston emerges from the pedestrian underpass below the drive and briefly stretches before embarking on a 4-mile run. It’s 5:05 a.m.
“Yeah, my friends think I’m nuts being out here this early,” the Northwestern University physical therapy student said. “But it is a heck of a lot cooler now than it will be after class at 5 p.m.”
Back at the Underground Wonder Bar, it’s nearing 6 a.m. The house lights came up hours ago and manager Darlene Gunette and hostess Lorna Boston are the only ones still there.
As she prepares for tomorrow’s late night, Boston attempts to summarize after-hours in Chicago.
“You see, sometimes people don’t understand,” she said. “The world does not stop after 9-to-5 or even after midnight. There are 24 hours in every day, and people are out here all over the city doing something during every one of those hours.”




