Fright Hike: Chicago Halloween Bike Tour — Haunted Loop & Lakefront Ride
Ride through Chicago’s night as guides illuminate haunted buildings, forgotten disasters and lakeside lore. This three-hour Halloween bike tour combines local history, urban architecture and spooky storytelling—perfect for riders who want a different kind of city night.
The Experience
Before You Go
Bring layered clothes
Lake Michigan’s breeze makes evenings cooler than daytime; pack a jacket you can stow in a bag.
Use a charged phone and light
Although bikes include front and rear lights, a phone flashlight with extra battery helps in alleyways and for emergency navigation.
Know your braking and hand signals
This tour moves through urban traffic and busy intersections—basic bike handling keeps you safe and the group together.
Tip your guide
Guides are storytellers and safety monitors; $10+ per person is the suggested gratuity, payable cash or electronic.
Local Knowledge
Hidden Gems
- •Lurie Garden (Millennium Park) for a quiet green pause on the route
- •The small Eastland Disaster plaque and historic markers along the riverwalk that most visitors miss
Wildlife
- •Canada goose
- •Great blue heron
Conservation Note
High pedestrian and bike use makes staying on designated paths important; pack out trash and avoid disturbing shoreline vegetation to protect Lake Michigan’s nearshore habitat.
The tour threads through sites tied to Chicago’s rapid growth, its 19th-century World’s Fair era and several high-profile tragedies like the SS Eastland disaster and the Iroquois Theatre fire of 1903.
Photographer's Notes
- • Outside the John Hancock Center for skyline-lit facades
- • Congress Plaza Hotel entrance for moody architectural shots
- • Lakeshore Drive near Museum Campus for long exposures of the water and city lights
What to Bring
Closed-toe shoesEssential
Secure footing for pedaling and quick stops on city streets.
Light jacket or windbreakerEssential
Keeps you warm on the cooler lakeshore breeze after sunset.
Small hydration bottleEssential
Staying hydrated matters even on an evening ride—pack a small refillable bottle.
Portable phone charger
Ensures your phone stays powered for photos and emergency use during the three-hour tour.
Common Questions
How long is the tour and how far do we ride?
The tour runs about three hours and covers roughly nine miles of mostly flat, urban pavement.
Are bikes and helmets provided?
Yes—bicycles and helmets are provided, including front and rear lights for night riding.
Is the tour suitable for children?
Children must be strong, capable riders able to manage approximately nine miles; child bikes, seats and tag-alongs are available—confirm when booking.
What happens in bad weather?
Tours run rain or shine; extreme weather may force cancellation, in which case you’ll be offered an alternative or refund.
Where does the tour start and end?
The tour starts and ends at Bobby’s Bike Hike headquarters at 540 N. Lake Shore Drive—arrive 15 minutes early for fit and briefing.
Is tipping expected for guides?
Tipping is customary—$10 per person or more is suggested and can be given in cash, Venmo or PayPal.
Book This Experience
Check AvailabilityDuration
3 hours
Location
Chicago, Illinois
Difficulty
moderate
Fitness Level
Moderate fitness; ability to ride roughly 9 miles on a city bike and handle stop-and-go traffic.
Ready to Explore Chicago?
Book your guided walking tour and discover the hidden stories of this historic mountain city.
Check Availability & Book Now