CHICAGO, IL

THE ORIGINAL BYOB HOLIDAY LIGHTS TROLLEY

CHICAGO, IL

  • 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.

  • 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.

  • 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.

  • 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 BYOB CHICAGO HOLIDAY LIGHTS TROLLEY TOUR

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—admission included!

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!

📍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