Private Trolleys and Charters for Chicago’s Holiday Season
When the streets of Chicago begin to glow and the chill in the air turns crisp, it’s time to start planning how you’ll celebrate the season. From neighborhood light displays to downtown festivities, there’s something magical about the city in winter. Whether you’re coordinating transportation for a company holiday party, a family outing, or a night of sightseeing, Aries Charter Transportation makes it easy to travel together.
For years, groups across Chicagoland have counted on Aries Charter for dependable, comfortable, and fun holiday transportation. Our private trolleys, charter buses, and vans are available for everything from intimate gatherings to large company celebrations. The best part? You get to focus on the event while we handle the driving, logistics, and parking.
Why Chicago Shines During the Holidays
There’s no place quite like Chicago in December. The lights along Michigan Avenue, the tree at Millennium Park, and the festive displays at Lincoln Park Zoo create a citywide celebration. Whether you’re local or visiting, it’s easy to spend an evening taking it all in—especially when you don’t have to worry about traffic or where to park.
That’s where a private trolley or charter bus comes in. Instead of coordinating carpools or multiple rideshares, your whole group can stay together, enjoying the scenery and conversation as you move from one stop to the next. A holiday outing feels more special when everyone arrives at once, ready to celebrate.
Holiday Lights Tours in Chicago
Our holiday lights tours are among the most popular ways to enjoy the season. Choose from classic routes through downtown or create a custom itinerary featuring your favorite neighborhoods. Many groups start with an early dinner before setting out to see the displays at Lincoln Park ZooLights, The Magnificent Mile, or Buckingham Fountain. Others prefer a suburban route through well-known residential displays.
Each tour is private and fully customizable. Whether you’re planning a cozy evening for friends or a large group event, we’ll help you build a route that fits your schedule and preferences. And yes, all of our trolleys and buses are enclosed and heated—perfect for those frosty December nights.
Company Holiday Parties and Corporate Events
Holiday transportation isn’t just for sightseeing. Many local businesses rely on Aries Charter to move employees and guests safely between the office, restaurants, or venues. Our fleet includes a range of vehicle sizes so you can match your group’s needs—whether that’s a 30-passenger trolley for a small department outing or a full-size motorcoach for a corporate holiday party.
Coordinating group transportation also helps reduce stress on your guests. Instead of navigating traffic or arranging parking, everyone can relax, enjoy the celebration, and get home safely. It’s a thoughtful touch that reflects well on your company and sets the tone for a well-organized event.
Vehicles Available for the Season
Holiday Trolleys
A Chicago favorite, our trolleys bring nostalgic charm to any outing. They’re perfect for lights tours, parades, and festive gatherings, featuring comfortable seating, wide windows for viewing, and onboard heat to keep everyone warm.
Charter Buses
For large groups, our motorcoaches provide spacious interiors, luggage storage, and professional drivers experienced in navigating winter conditions. Ideal for galas, fundraisers, or end-of-year corporate celebrations.
Executive Vans and Minibuses
Smaller parties can enjoy the same professional experience in our vans or minibuses. They’re a great fit for family celebrations, client dinners, or smaller holiday tours.
Each vehicle in the Aries fleet is maintained to the highest standards and operated by trained, uniformed drivers who know the city and suburbs well.
Planning Your Holiday Transportation
The holidays are one of the busiest times of the year for group transportation in Chicago, so early reservations are encouraged. December weekends fill quickly, especially for trolley rentals. Booking three to four weeks in advance ensures your preferred vehicle and departure time.
When planning your outing, think about:
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Group size: The number of passengers helps us match you with the right vehicle.
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Pickup and drop-off locations: We can accommodate multiple stops or direct point-to-point service.
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Timing: Consider how long you’ll spend viewing lights, dining, or attending your event.
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Amenities: Let us know if you’d like bottled water, music, or special decorations onboard.
Our team can help fine-tune the details so your evening runs smoothly.
Custom Routes and Stops
Every holiday outing is different. Some groups want to spend extra time downtown admiring the window displays on State Street; others want to explore neighborhoods like Lincoln Park, Wrigleyville, or Naperville. You can provide a full itinerary or let our staff suggest a route based on what you’d like to see. We’ll plan efficient travel times, confirm any venue access points, and coordinate parking so your group can enjoy the evening without interruptions.
Why Groups Choose Aries Charter
Aries Charter has been part of Chicago’s transportation scene for decades, serving local schools, corporations, and community groups throughout the year. During the holidays, our experience shows in every detail—from well-timed arrivals to courteous drivers who understand how to navigate busy city streets.
Groups choose us because:
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We’re locally owned and operated in Chicago.
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Our drivers are trained professionals familiar with city routes and winter conditions.
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The fleet includes trolleys, minibuses, and full-size coaches for any group size.
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Booking is simple, with dedicated support for event coordination.
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We operate through every type of weather Chicago can deliver.
Whether you’re arranging a one-night celebration or a full week of corporate events, we’ll help make sure transportation is one less thing to worry about.
Ready to Reserve?
Now is the perfect time to plan your holiday transportation in Chicago. From lights tours and parties to concerts and seasonal attractions, a private trolley or charter keeps your group together and lets you enjoy every part of the celebration.
To request a quote or reserve your vehicle, visit ariescharter.com or call 773-826-2000. Our team will help confirm details, vehicle options, and availability for your date.
When the lights come on and the city starts to sparkle, there’s only one thing left to say—all aboard for the holidays.