Sightseeing Cruises

Chicago Haunted River "Creepy Cruise" by First Lady

4.0/5(10)

Randell M

Couple

Verified booking

Sep 2026

My wife and I did this cruise for our anniversary. It was romantic to see the city lit up from the river. To top it off we got alot of really cool spooky history that brought the whole experience together. The tour guide was knowledgeable and friendly. Ended the night by seeing the fireworks going off at navy piere. Sound system was clear. We 100 percent woukd do this again just for the breathtaking sites of the city at night.

Elizabeth G

Couple

Verified booking

3 weeks ago

It was fun learning a different type of history about the city. The guide was also very knowledgeable about things outside of the tour - I'm from California, so he gave good advice on things to do in the city.

Elicia N

Solo

Verified booking

Jul 2026

Andy was amazing! Went on the creepy nighttime boat tour focused on Chicago crimes. His stories and personality are perfect and loved the cheesy bits he added in! Would highly recommend this tour to others! Still talking about his stories the next day. Also appreciated him addressing the people loudly talking and laughing right in front of him while he was story telling.

Timothy P

Family

Verified booking

Jun 2026

This was a great cruise, very informative! Our tour guide/MC, Doug, was incredible at his craft. His storytelling of local lore and historical trauma, coupled with the ambience of the city at night, created a truly entertaining and spooky evening! Will definitely attend one of his other tours!

Jill A

Couple

Verified booking

Jun 2026

Great stories!! It would be nice if he talked louder. There were other noises going on outside the boat, other boats blasting their music, going under the train tracks, and the driver blaring his horn. So at times we missed part of the story.

Experience a 90-minute nighttime cruise along the Chicago River, where a lively guide shares chilling stories of haunted history, mobsters, eerie sightings, and hidden secrets tied to the city’s past.

Depart from 111 E. Wacker Dr. along the Chicago Riverwalk and enjoy a guided tour featuring the city skyline at night, historic bridges, and landmarks connected to ghost stories and infamous figures.

Relax with general admission seating and access to both open-air upper decks and enclosed lower salons, with onboard restrooms, stroller storage, and assistance options for limited mobility guests.

Purchase snacks, beer, and wine onboard while enjoying an immersive storytelling experience that brings Chicago’s darker riverfront history and legends to life.

Upgrade to skip-the-line boarding for faster access and enhanced seating or commentary options, with cruises operating rain or shine for a flexible evening experience.

Night cruise featuring haunted landmarks on the Chicago River

90-minute guided cruise

Local guide onboard

Live commentary

Access to the open-air upper deck and enclosed lower deck

Restrooms onboard

Beer & wine bar and snack bar (available for purchase onboard)

Free stroller storage

Wheelchair accessible restrooms on select vessels

Children under 4 ride free

Priority boarding with skip-the-line access (as per option selected)

General boarding (as per option selected)

Food and beverages (available for purchase onboard)

Gratuities

Parking

TOTAL DURATION1 hour 30 minutes
FREQUENCYFrom March to November
MODE OF TRANSFERBoat
1 Boarding point
Chicago Riverwalk, near Michigan Avenue
Get direction
Sights covered
Goose Island
Historic Montgomery Ward Complex
Erie on the Park
Bally's Chicago Casino Site
Merchandise Mart
Riverbank Lofts
Wolf Point
100 North Riverside Plaza
Chicago Mercantile Exchange
Willis Tower
Civic Opera House
333 West Wacker
Marina City
Trump International Hotel & Tower
Aon Center
Tribune Tower
NBC Tower
St. Regis Chicago
DuSable Harbor

These tickets can't be cancelled or rescheduled.

10 reviews
How do we collect reviews?
These ratings include verified reviews from both Headout guests and our trusted partners who operate this experience locally. All reviews come from real travelers who've taken this experience.
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What our guests say
Elizabeth G
Couple
Verified booking
3 weeks ago
It was fun learning a different type of history about the city. The guide was also very knowledgeable about things outside of the tour - I'm from California, so he gave good advice on things to do in the city.
Josh B
Solo
Verified booking
2 weeks ago
Excellent tour. The crew and sights was great.
Randell M
Couple
Verified booking
Sep 2026
My wife and I did this cruise for our anniversary. It was romantic to see the city lit up from the river. To top it off we got alot of really cool spooky history that brought the whole experience together. The tour guide was knowledgeable and friendly. Ended the night by seeing the fireworks going off at navy piere. Sound system was clear. We 100 percent woukd do this again just for the breathtaking sites of the city at night.
Elicia N
Solo
Verified booking
Jul 2026
Andy was amazing! Went on the creepy nighttime boat tour focused on Chicago crimes. His stories and personality are perfect and loved the cheesy bits he added in! Would highly recommend this tour to others! Still talking about his stories the next day. Also appreciated him addressing the people loudly talking and laughing right in front of him while he was story telling.
Kathleen M
Couple
Verified booking
Jul 2026
I enjoyed the scenery, the boat ride, and the entertaining stories

What to bring

Bring a valid photo ID if you plan to purchase drinks from the onboard beer and wine bar.

Carry a light jacket or an extra layer, as temperatures on the river can feel cool.

What's not allowed

Luggage and oversized bags are not allowed onboard or at the dock, and storage facilities are unavailable.

Outside alcoholic beverages are not permitted on the cruise.

Pets and emotional support animals are not allowed, except for ADA-defined service dogs; dogs are only permitted on designated Canine Cruises.

Tickets cannot be refunded or exchanged for any reason.

Accessibility

Some vessels include accessible restrooms and changing tables, while others may not, so guests should verify vessel-specific facilities in advance.

Assistance for guests with limited mobility, including early boarding and river-level drop-off support, is available upon request.

Since the Riverwalk does not have elevators, guests requiring ADA access can use the ramp at State Street and Wacker Drive within Vietnam Memorial Park and continue east under the Michigan Avenue Bridge to reach the dock.

Detailed accessibility information for docks and vessels is available on the operator’s official accessibility page.

Additional information

Arrive at least 30 minutes before departure for check-in; priority boarding begins 20 minutes before departure, and general boarding starts 15 minutes prior.

Seating is general admission, and all guests are guaranteed outdoor seating.

Children under 4 years old ride free but still require a ticket, and strollers must be folded and stored in the salon during the cruise.

Cruises run rain or shine, with enclosed lower decks available during poor weather.

This cruise route does not pass through the Chicago Harbor Lock.

Restrooms are available onboard, and select vessels also offer accessible bathrooms and changing tables.

Discounted parking is available at 111 E. Wacker Dr. with validation from the ticket office or bartender if the office is closed.

Mobile tickets are accepted at the dock, so printed tickets are not required.

Beer, wine, snacks, and other refreshments are available for purchase onboard.

For safety reasons, onboard restrooms close 15 minutes before the tour ends.

Your voucher will be emailed to you shortly.

Display the voucher on your mobile phone with a valid photo ID at the starting point.

Please check your final voucher for the starting point details & specific instructions.