with Second City Sirens Scooters,
Chicago's first and only dedicated Vespa rental experience
cruise the Windy City on a classic Vespa or Stella
Tour Chicago with our fleet of beautifully maintained scooters, each named after the remarkable women who shaped our city's history.
We know every curve of Chicagoland's streets – from the bustling Loop to scenic lakefront paths and charming suburban routes. Whether you're craving an urban adventure past iconic landmarks or a peaceful countryside escape, we've got the perfect ride and route for you.
Experience Chicago's beauty and architectural heritage through the eyes of a local expert. Our curated routes combine scenic riding with fascinating stops, all guided by someone who knows both the city's streets and its stories. Enjoy complimentary personalized route maps with your rental!
Guided tours available with a local expert
What makes us different?
Second City Sirens is a minority woman-owned, rider-focused service that welcomes everyone. We offer both automatic and manual transmission options at Daily, weekly, and monthly rentals. We provide complimentary helmets and personalized route maps with your scooter rental.
Chicago's only Vespa & Stella rental company
Learn to ride safely in a supportive, approachable environment. We are especially welcoming to women who want to learn on appropriately-sized bikes without intimidation
MSF training and testing for Class M & L licenses
New to RiderShare? The platform handles all payments, insurance, and booking logistics, making your rental experience seamless and secure.
How to Book
- Download RiderShare on your phone or visit their website using this referral link.
- Choose between Koko (automatic Vespa GTS) or Ida (manual Stella 4T)
- Select your rental dates and complete the booking
- You can choose to pick up or have the bike delivered (for a small fee).
- You can also choose to rent a helmet, we offer both full-face and half-helmets.
Current rates and availability can be found on our RiderShare listings. Daily, weekly, and monthly options available.
Pricing & Packages
Our fleet of historic sirens is currently available through RiderShare, the premier motorcycle sharing platform. With just two beautifully maintained scooters ready to roll we're offering an exclusive, personalized rental experience while we grow our fleet.
Meet Our Fleet of Sirens
About Ida B. Wells (1862-1931)
A fearless journalist and civil rights pioneer, Ida B. Wells used her pen as a weapon against injustice, investigating lynchings across the South and exposing uncomfortable truths that others wouldn't dare print. After threats forced her to flee Memphis, she made Chicago her base and continued her crusade for equality, co-founding the NAACP and establishing the first Black women's suffrage club. Like our reliable Stella that bears her name, Wells was built for the long haul – determined, uncompromising, and willing to take the difficult path when justice demanded it.
Ida
From pioneering activists and groundbreaking artists to visionary architects and fearless entrepreneurs, these extraordinary individuals shaped the city we know and love today. As you explore Chicago's streets, you'll be riding alongside the legacy of women who challenged conventions, broke barriers, and built a better tomorrow. Each of our beautifully maintained Vespas and Stellas comes with the story of its namesake – because every ride should be an adventure through both the city's landscape and its inspiring past.
150cc 4-stroke single cylinder engine
Manual 4-speed transmission
Kick start
60 mph top speed
10" wheels with drum brakes
Based on classic Vespa PX design
Fuel capacity: 1.8 gallons
Single rider optimized
Every scooter in our collection carries the name and spirit of a remarkable woman who left her mark on Chicago's history.
2013 Stella 4T
About Koko Taylor (1928-2009)
Known as the "Queen of Chicago Blues," Koko Taylor commanded stages across the city with a voice that could shake the foundations of the toughest blues clubs. Her signature song "Wang Dang Doodle" became a blues anthem, and she spent decades breaking barriers in a male-dominated industry while earning a Grammy and multiple Blues Music Awards. Like our powerful GTS that bears her name, Koko Taylor proved that with enough soul and determination, you could make the whole city listen.
Koko
278cc 4-stroke single cylinder engine
Automatic CVT transmission
Electric start
75+ mph top speed
12" wheels with disc brakes front and rear
Under-seat storage compartment
Fuel capacity: 2.2 gallons
Comfortable two-person seating
2009 Vespa GTS
Featured Tours
Routes & Tours
Gold Shore Scenic Tour
Cruise Chicago's stunning lakefront from the vibrant North Side all the way to the magnificent Bahá'í Temple in Wilmette. This breathtaking route hugs Lake Michigan's shoreline, taking you past iconic beaches, harbors, and neighborhoods while offering endless views of the water. Perfect for riders seeking natural beauty and peaceful stretches away from city traffic.
Prairie Style Architecture Tour
Start in historic Oak Park, birthplace of Frank Lloyd Wright's revolutionary Prairie School movement, then wind through carefully selected downtown locations showcasing the architectural genius that defined Chicago. As an architecture student specializing in Chicago's building history, your guide will reveal hidden details and stories that most visitors never discover.
Custom Adventures Available
From hidden neighborhood gems to historical deep-dives, we offer additional specialized tours tailored to your interests. Contact us to discuss route options including urban exploration, foodie destinations, mural tours, and more off-the-beaten-path Chicago experiences.
All tours include route maps, historical context, and insider recommendations for the best stops along the way.
Experience Chicago's beauty and architectural heritage through the eyes of a local expert. Our curated routes combine scenic riding with fascinating stops, all guided by someone who knows both the city's streets and its stories.
Safety & Equipment
know before you ride
Your safety is our top priority, and we provide everything you need for a confident, enjoyable ride through Chicago. We'll provide a thorough safety briefing covering Chicago-specific riding tips, traffic patterns, and route recommendations based on your experience level.
What's Included:
Pre-ride safety inspection of your chosen scooter
Detailed briefing on Chicago traffic and parking
Emergency contact information
Route maps with safety notes and recommended stops
We recommend wearing closed-toe shoes, long pants, and bringing a light jacket for lakefront routes. Our scooters are regularly maintained by experienced mechanics, and we'll walk you through basic controls and features specific to your Vespa or Stella before you hit the road.
Illinois Licensing Requirements
In Illinois, motor-driven cycles with less than 150cc require a Class L license, while motorcycles with 150cc or greater require a Class M motorcycle license. Our Stella 4T (149cc) requires a valid Class L license, while our Vespa GTS (278cc) requires a Class M license.
Questions about safety gear or licensing requirements? Contact us directly for personalized guidance.
