CHICAGO, IL

THE ORIGINAL BYOB HOLIDAY LIGHTS TROLLEY

CHICAGO, IL

  • People waiting in line to ride a decorated trolley on a city street at night during the holiday season, with festive lights adorning the trolley and storefronts.

    Check-In at a Neighborhood Bar

    Meet at Matilda (3101 N Sheffield) and kick off the night with festive decor, a complimentary snack, and meet-and-greet your tour guide before the ride begins.

  • A decorated trolley with Christmas lights and wreaths on a city street during evening, with a person wearing a Santa hat inside.

    Hop on a Festive Trolley

    Enjoy holiday music, trivia, prizes, and sing-alongs to classic carols as you ride through the city. The festive trolley decor sets a cheerful tone from start to finish.

  • Group of people celebrating Christmas, wearing Santa hats and holiday sweaters, holding drinks, and smiling inside a festive setting.

    Bring Your Own Beverages

    Trolleys are 21+. Sip on your favorite holiday spirit as you ride in style aboard our vintage trolley. It's the perfect way to toast the season while taking in the city’s festive sights.

  • Group of people wearing Santa hats taking a selfie at a Christmas event with festive lights and decorations in the background.

    Enjoy Your City's Holiday Lights

    Tour stops vary by date, but highlights may include Christkindlmarket, The Magnificent Mile, Millennium Park’s Christmas Tree, and Lincoln Park ZooLights—ZooLights admission included with your ticket.

WELCOME TO THE CHICAGO BYOB HOLIDAY LIGHTS TROLLEY

Experience Chicago’s top holiday sights like never before!

Climb aboard a vintage BYOB trolley for a one-of-a-kind ride through the city’s most iconic holiday landmarks. Your night kicks off at Matilda, where festive decor and a complimentary snack set the tone. Then, it’s off to explore sparkling sights like Christkindlmarket, The Magnificent Mile, Millennium Park’s Christmas Tree, and Lincoln Park ZooLights—ZooLights admission included with your trolley ticket!

Please note: stops are not guaranteed and may vary nightly based on traffic, timing, and availability.

You’ll enjoy music, trivia, prizes, and holiday cheer all night long, with a tour guide leading the way and a souvenir gift to take home.

Book your trolley ride today and light up your holiday season!

Holiday sign with Christmas lights and red and white diagonal stripes border, reading 'Know Before You Go'

📍Check-In Location

All guests must check-in at Matilda's, located at: 3101 N. Sheffield, Chicago, IL 60657.

Please arrive at your event start time.

*Please note the length of the event is 4 hours. The first hour is spent at the check-in bar (meet your guide, sign paperwork, get your gift bag & complimentary snack) followed by a 3 hour trolley route which will make stops! 

🚗Parking

Parking is not included with your ticket. Plan to arrive a little early to get a parking spot before boarding the trolley.

Matilda itself does not have parking. While there is street parking in the Belmont neighborhood, we advise using services like Spot Hero to guarantee your spot. A short distance away is also Advocate Illinois Masonic Hospital, which many prior guests have used.

Alternately, Matilda is just steps away from the CTA Belmont Red Line stop, which is a major hub for both train and bus transit.

👋When You Arrive

Look out for your spirited host wearing a red scarf and possibly wielding a flashing candy cane stick. Get ready to sign our event waiver before the trolley embarks promptly at departure time. Be prepared to show a valid ID verifying you are over the age of 21.

🍻BYOB

BYOB for the trolley, but ask your tour guide at the check-in table where you can store your drinks prior to boarding the trolley. Each host bar has a fantastic selection of additional spirits. If your drinks come in glass bottles, you are welcome to bring them onboard, however we ask that you pour the drink into a different non-glass container while on the trolley. We will provide you plastic cups that you can use.

Remember, no open containers outside the trolley. Beverages can be stored in personal-sized coolers (think: what can fit under an airline seat). 

🧣Attire

While the trolley and the bars are heated, we will stop at various locations around the city that are not. We recommend dressing in layers and bringing hats, scarves, and mittens so you can have an enjoyable experience as you get up close to the light displays at each stop.

EVENT & TROLLEY SCHEDULE

  • 3-7PM TICKET

    3:00-3:15pm - Arrive for Check-In at Matilda

    3:15-3:45pm - Meet your guide & Complimentary snack at Matilda

    4:00pm - Trolley Loading & Departure

    4:00-7:00pm - Trolley ride with stops at Christkindlmarket and ZooLights

    *Bathrooms available at both stops

    7:00pm - Trolley arrives back to Matilda & Event Ends

  • 4-8PM TICKET

    4:00-4:15pm - Arrive for Check-In at Matilda

    4:15-4:45pm - Meet your guide & Complimentary snack at Matilda

    5:00pm - Trolley Loading & Departure

    5:00-8:00pm - Trolley ride with stops at Christkindlmarket and ZooLights

    *Bathrooms available at both stops

    8:00pm - Trolley arrives back to Matilda & Event Ends

  • 5-9PM TICKET

    5:00-5:15pm - Arrive for Check-In at Matilda

    5:15-5:45pm - Meet your guide & Complimentary snack at Matilda

    6:00pm - Trolley Loading & Departure

    6:00-9:00pm - Trolley ride with stops at Christkindlmarket and ZooLights

    *Bathrooms available at both stops

    9:00pm - Trolley arrives back to Matilda & Event Ends

  • 6-10PM TICKET

    6:00-6:15pm - Arrive for Check-In at Matilda

    6:15-6:45pm - Meet your guide & Complimentary snack at Matilda

    7:00pm - Trolley Loading & Departure

    7:00-10:00pm - Trolley ride with stops at Christkindlmarket and ZooLights

    *Bathrooms available at both stops

    10:00pm - Trolley arrives back to Matilda & Event Ends

  • People waiting in line to board a red trolley decorated with Christmas lights on a snowy sidewalk at night.
  • A Christmas market stall with colorful glass ornaments, Christmas decorations, and lighting, with people browsing and chatting.
  • People taking photos at a festive outdoor light display with colorful illuminated trees and sculptures at night.
  • A couple wearing Santa hats and festive Christmas lights around their necks taking a selfie at a holiday event with colorful lights and decorated trees in the background.
  • People celebrating Christmas wearing Santa hats and festive holiday accessories, holding drinks, and laughing together.
  • People standing in line at a Christmas market stall decorated with lights and garlands in an urban setting at night.
  • Two people wearing winter hats and scarves at night, taking a photo of a lit-up outdoor pool area with colorful lights and trees in the background.

Fine Print: Event is 21+. All attendees must have valid ID at check-in. All sales are final and tickets are non-refundable. Tickets are only valid for event date and event time. No refunds or reschedules will be provided to anyone who misses scheduled event. Event is rain, shine or snow. No refunds will be given to customers who do not attend the scheduled event due to weather. Ticket transfer requests to change your trolley date/time will be accepted for a limited time. Transfers are subject to availability. After 10/1/25 ticket transfer requests will no longer be accepted.

Vehicle accommodations and arranged sightseeing are subject to change at any time due to unforeseen circumstances or circumstances beyond Holiday Lights Trolley control. Every effort will be made to operate tours as planned, but alterations may occur. Holiday Lights Trolley reserves the right to change vehicles and to make alterations to the itinerary or the tour as it deems necessary. Stops and sights are not guaranteed and may vary nightly based on traffic, timing, and availability.

The trolley driver and guide are responsible for the route of the trolley. The route for each public tour is set and we are unable to take requests for stop changes or substitutions from customers for any reason.**