Frequently Asked Questions

Q: How do I reserve?
A: Reserve online by clicking here. You can also call us 312-972-3271 or email us  for the fastest response at [email protected]

Q: What is the best way to reserve?
A: In order to remain efficient and affordable we recommend you make a reservation online. After filling out the form, if the reservation time is available you will receive a confirmation within 48 hours. Upon our confirming the reservation you will be asked for 50% deposit on your reservation. Final Balance is due prior to the event date (see contract).

Q: Is there a minimum amount of rental hours?
A: Yes, we do have a minimum rental of 3 consecutive hours.

Q: Do the trolleys operate all year around?
A: Yes, they are fully heated and air conditioned (see below) and operate the same as any other type of bus.

Q: What’s included in your rates? Are there additional fees for gas, city taxes or travel times to/from the garage?
A: Our rates mainly depend on the total amount of consecutive time of your rental on that specific date. The time starts when we ARRIVE at your initial pick-up location. All of our rates include every cost EXCEPT; *Driver’s gratuity – Which is at your discretion… See below. * A possible clean-up fee may apply for significant messes… See below.

Q: Do you have any special rates or promotions?
A: FRIDAYS & SUNDAYS ARE $500 FOR UP TO 5 HOURS OF SERVICE. Also see the discounts on Wedding and Event Coordination through our sister company WC Event Group

Q: What is the typical amount given for driver’s gratuity?
A: We normally suggest 10-12% for most events, 12-15% for weddings and bar crawls.

Q: What do your drivers wear?
A: Black or Khaki Pants and white collared shirt. Tie for a wedding.
Q: Can food and drinks be brought on board the vehicles?
A: We do allow food and drinks on board our vehicles however; We DO NOT provide Coolers. NO Glass bottles. Champagne is the exception for a wedding.

Q: What is the clean-up fee for?
A: We know there will be spillage of food and drinks and this clean-up fee is applied if the vehicle needs significant cleaning after the job has finished.

Q: Can the trolley cars go on the highways?
A: Yes our trolley cars can access highways and travel at the same speeds just as any regular bus can.

Q: Do all of the vehicles have the same interior/exterior design?
A: All of our trolley cars are identical inside and out.

  • Exterior Colors are Black & Khaki

  • Seating for up to 32 Guests

  • Air Conditioned and Heated (see contract disclaimer below)

  • Open-Air Option (seasonal)

  • Oak Benches that are Forward Facing

  • Wheelchair Lift (some vehicles)

  • AM/FM with C.D. & iPod Capability (4 S)

Q: Are your vehicles air-conditioned/heated?
A: Windy City Trolley, Inc. trolleys do come equipped with AC units; however WCT will not guarantee complete AC satisfaction for your charter. Trolleys are built to be open-air vehicles in the warmer months or enclosed and heated in the winter.  For trolleys, air conditioned air does not circulate like a leisure bus, limo or standard car.  Trolleys are not designed to sustain full AC capabilities like other vehicles.  Windy City Trolley does not guarantee that the AC unit will provide the level of comfort that the client may desire.  Windy City Trolley, Inc. will not refund any payment due to the dissatisfaction of the temperature from the AC inside of the vehicle.

Q: Are the sides open or closed in the winter?
A: The trolley cars all have two types of side panel inserts. During the colder months (between Halloween and St. Patrick’s Day) the trolleys will have solid sides panels with small windows that may be opened. During the warmer months (Memorial Day to Halloween) the trolley cars will have the open-air option.

Q: Are the sides always open?
A: In the warmer months yes.

Q: Are standees permitted?
A:. No standees are permitted while on highways and other noted streets.

Q: Is there accessibility to play music?
A: Yes we have an AM/FM radio, CD player and an auxiliary cord for iPods (4S)

Q: Are there seatbelts on your trolley cars?
A: Our trolley cars do not have seatbelts.

Q: Are your vehicles wheelchair accessible?
A: Certain vehicles please confirm with booking agent if vehicle is available.

Q: Can we bring our own decorations for the trolley?
A: We do allow decorations however, limitations apply. You can decorate the trolley when it arrives at your initial pick-up, no earlier. We also require you to use painters tape only or the tape and string supplied by our drivers, no staples, tape or glue can be used. We also restrict covering certain windows and any exterior lighting for safety reasons.

Q: Can we make signs to go on the outsides of the trolleys?
A: Yes

Q: What types of events/groups use your vehicles?
A: Weddings, corporate events, parades, birthdays, family gatherings, bachelor/bachelorette parties, holidays, city tours, trips to the airport… anything you may need transportation for.

Q: Are children allowed on board?
A: Children are allowed on board with supervising adults, but keep in mind that we do not have seat belts on our trolley cars.

Q: Are there specific hours of operation? Or do you provide services at all hours of the day?
A: We provide services as early as 5:00am and as late as 12:00am Sunday to Thursday and 5:00am to about 1:30am Fridays and Saturdays.

Q: How do I reserve a vehicle?
A: We’re on a first come, first served basis. Just call our main office line 312-972-3271  or for immediate service email [email protected] to speak to a staff member who will work with you to create your contract. They will then email you a contract. A vehicle isn’t reserved for you until we receive a signed contract with your credit card information for the nonrefundable deposit. You can fax, scan and email or send us a copy in the mail for processing. If a vehicle is still available, you will then receive an email or fax with your confirmation and receipt of payment.

Q: What if I need to cancel?
A: Cancellation Policy Events cancelled more than thirty (30) days prior to the event will be refunded twenty-five (25) percent of the fifty (50) percent required deposit if written cancellation is submitted no less than thirty (30) days prior to the event date.  The retained twenty-five (25) percent will compensate Windy City Trolley, Inc. for not offering the date and service to other potential clients.  Clients are responsible for paying 100% of the balance in the event of cancellation within ten (10) business days prior to the scheduled charter.

Q: What methods of payment are accepted?
A: We require all deposits to be made in credit card, all major credit cards and do not charge processing fees. We also accept checks for additional payments.Deposit
We require a 50% deposit to secure the date of your event, which is a nonrefundable fee in the event of cancellation within 30 days prior to the event date.

Q: How do we get in contact with the driver during the service, just in case?
A: Drive cell numbers will be provided 24 hours before the event. We will provide driver with cell number on file for host for the driver that day.It is the responsibilty of the host to provide the driver with any other numbers that they want driver to have. If you need anything day of, you can always contact our main office [email protected]

Q:Will the driver know where to go? Do you have a GPS system?
A: No we do not have a GPS system on board (too distracting) Host is responsible for providing WCT with a route  3 days prior if they want it to be mapped for the driver ahead of time. Otherwise the route taken is entirely up to our drivers judgment unless the customer specifies a particular route in advance.

Q: Does WCT offer any other services?
A: Receive a $100 off your trolley when you book a Wedding Day /Event Coordinator through us with WC Event Group. Cannot be combined with any other offer.