There’s a certain charm to street names, isn’t there? They’re woven into the fabric of our cities, guiding us, marking our addresses, and sometimes, just sometimes, making us giggle. For Chicagoans, “Whipple Street” is one such name. Running north-to-south through neighborhoods like Albany Park, Logan Square, and Beverly, just west of Sacramento Avenue, Whipple Street has an undeniable comedic ring. It’s the kind of name that can elicit a fit of giggles on a school bus, becoming an inside joke, a rallying cry.
Inspired by a Twitter user’s recent observation about the delightful absurdity of “Whipple Street,” we started thinking: What other Chicago street names are secretly hilarious? A deep dive into Google Maps and the city’s extensive street name database revealed a treasure trove of contenders. Prepare for a chuckle as we explore the funniest street names Chicago has to offer.
Streets That Tickle Our Funny Bone
Some street names just have that je ne sais quoi that makes you smirk. Maybe it’s the sound, maybe it’s the unexpected juxtaposition of words, but these Chicago streets are guaranteed to elicit a chuckle every time you hear them:
- Busse Ave.
- Crilly Ct.
- Gole Dr.
- Hoey St.
- Hooker St.
- Hurlbut St.
- Laflin St.
- Lovejoy Ave.
- Tonty Ave.
- Whipple St.
It’s hard to pinpoint exactly why these names are funny. Is it the playful sound of “Whipple”? The unexpected bluntness of “Hooker”? Or the sheer silliness of “Gole”? Whatever the reason, these streets have earned their place on our list of Chicago’s funniest.
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Streets Named After Your (Hypothetical) Grandparents
There’s a certain nostalgia, a gentle humor, in street names that sound like they belong to someone’s grandparents. These Chicago streets evoke images of cozy homes, Sunday dinners, and maybe a slightly old-fashioned sensibility:
- Cyril Ave.
- Delphia Ave.
- Evelyn Ln.
- Hazel St.
- Hortense Ave.
- Jean Ave.
- Joyce Ln.
- Leona Ave.
- Leroy Ave.
- Luella Ave.
- Tom Pkwy.
Imagine telling someone you live on Hortense Avenue! These names are a reminder of a different era, adding a touch of quaint charm to the Chicago streetscape.
Streets That Trip You Up (If You’re Not From Around Here)
Chicago, like any city with a rich history, has its share of street names that are pronunciation puzzles for newcomers. These are the streets that might have you stumbling and fumbling until you finally learn the local lingo:
- Carondolet Ave.
- Dowagiac Ave.
- Goethe St.
- Honore St.
- Mies Van Der Rohe Way
- Paulina St.
- Wabansia Ave.
“Dowagiac”? “Honore”? Good luck to anyone trying to pronounce these correctly on their first try! These names are a badge of honor for long-time Chicagoans and a source of amusement (and perhaps a little frustration) for those still learning the ropes.
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Streets That Are Definitely NOT Fullerton
Fullerton Avenue is a major thoroughfare in Chicago, instantly recognizable. But what about its almost-but-not-quite namesakes? These streets live in Fullerton’s shadow, forever destined to be identified by what they aren’t:
- Cullerton St.
Cullerton Street. It’s close, but no cigar. It’s the almost-Fullerton, the Fullerton-adjacent. There’s a subtle humor in its near-miss status.
Streets With a Few Too Many Words
Sometimes, street names just get… ambitious. They try to pack in too much information, resulting in names that are more of a mouthful than a helpful identifier. Chicago has its share of these verbose avenues:
- East Drive of Oakley Ave.
- North Water Lower Street
- South Water Ramp Lower Street
- Sub Lower Wacker Drive
“Sub Lower Wacker Drive”? Try giving that address to a taxi driver! These streets are a testament to bureaucratic detail, taken to a slightly ridiculous extreme.
The California Dreamin’ Streets
Chicago isn’t exactly California, but you wouldn’t know it from some of its street names. These sun-soaked monikers transport you to the West Coast, at least in spirit:
- Alta Vista Terrace
- California Ave.
- Francisco Ave.
- Mango Ave.
- Pool Dr.
- Sacramento Ave.
- Surf St.
- Weed St.
“Surf Street” in Chicago? While Lake Michigan isn’t exactly known for its waves, these California-inspired names add a touch of sunny optimism to the Windy City.
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Streets That Sound Like They Belong Somewhere Else
Street names can be powerful in evoking a sense of place. And some Chicago streets seem to have gotten lost on their way to another city entirely. These names feel distinctly out of place in the Midwest metropolis:
- Avenues A, B, and C
- Central Park Ave.
- Churchill Row
- Commonwealth Ave.
- Harlem Ave.
- Harvard Ave.
- Narragansett Ave.
- New England Ave.
- Pensacola Ave.
- Ponchartrain Blvd.
- Wall St.
- Yale Ave.
“Wall Street” in Chicago? It just doesn’t quite fit. These names are like little geographical misplacements, adding a layer of unexpected humor to the city’s street grid.
Streets With a Certain Je Ne Sais Quoi (French Edition)
Chicago, despite its Midwestern roots, has a touch of French flair in some of its street names. These elegant, Gallic-sounding avenues bring a touch of Parisian sophistication to the city:
- Beaubien Ct.
- Dauphin Ave.
- Midway Plaisance
- Paris Ave.
“Midway Plaisance” – try saying that with a straight face! These French-inspired names add a touch of linguistic elegance, and perhaps a hint of playful pretension, to Chicago’s streets.
Streets Best Said With a British (or Scottish!) Accent
Accents can change everything, even the humor of a street name. Try saying these Chicago streets with a British or Scottish accent and see if they don’t suddenly become even funnier:
- Cheltenham Pl.
- Commodore Whalen Dr.
- Creiger Ave.
- Eggleston Ave.
- Elbridge Ave.
- Finsbury Ct.
Imagine a posh British voice announcing “Cheltenham Place”! Or a hearty Scottish brogue proclaiming “Creiger Avenue!” Suddenly, these streets take on a whole new comedic dimension.
Streets That Sound Like a City Mashup
Sometimes, street names sound like two other words smooshed together, creating a delightful (and slightly bizarre) linguistic hybrid. These Chicago streets are prime examples of accidental wordplay:
- Miltimore Ave. (Milwaukee + Baltimore?)
“Miltimore” – is it Milwaukee? Is it Baltimore? No, it’s Miltimore! This street name is a perfect example of how accidental word combinations can create unexpected humor.
Streets That Might Lead to the Underworld
And finally, for those with a darker sense of humor, there are the Chicago street names that sound like they belong in a gothic novel, or perhaps even a certain fiery realm:
- Dante Ave.
Dante Avenue. Does it lead to the Inferno? Probably not, but the name certainly conjures up images of epic poetry and maybe a little bit of hellfire.
The Street Name Champion
And finally, we arrive at the street name that truly reigns supreme, a name that is both meaningful and powerful:
- Ida B. Wells Drive
Ida B. Wells Drive is not just a street name; it’s a statement. Honoring the iconic journalist and activist, this name is a powerful reminder of Chicago’s history and the ongoing fight for justice and equality. While perhaps not “funny” in the traditional sense, the sheer audacity and importance of this name makes it, in our opinion, the absolute best street name in Chicago.
Chicago’s street names are more than just directions; they’re a reflection of the city’s history, its quirks, and its sense of humor. So next time you’re navigating the Windy City, take a moment to appreciate the funny side of its street signs – you might just find yourself chuckling along the way.
