Bachelor(ette) Parties

Windy City Trolley is your number one source for celebrating a Bachelor/ Bachelorette party, birthday party, or just a well deserved girls or guys’ night out on a party trolley. Round up your friends for an evening of serious celebrating; we’ll handle all the details and keep the night rolling with our friendly, and knowledgeable drivers. Whether you choose to ‘bar hop’ some of the liveliest clubs in Chicago or just cruise with your party through the streets of the city, let Windy City Trolley help make your night an unforgettable one for the bride or groom to be.

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We would be honored to transport your bridal party, family, friends and wedding guests to and from church, reception and iconic Chicagoland photo locations!

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Rehearsal Dinners

We can also provide unique transportation service for your wedding party, family, and friends to and from your rehearsal dinner – a great opportunity for your out-of-town guests to see the beautiful city of Chicago. Safe, fun, and unforgettable – let Windy City Trolley take care of you on your cherished day!

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Pub Crawls

Leave the driving to us and relax as you enjoy your party to its fullest! Cruise throughout the streets of Chicago listening to your favorite music and enjoying your favorite beverage..
Whether it’s a pub crawl to celebrate a birthday, an anniversary, a graduation or another special milestone, our Party Trolleys allow you and your guests to enjoy the evening in comfort and safety as our experienced, friendly drivers chauffeur your party to and from your destination, or just tour around beautiful Chicago for the evening.

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Corporate Outings

Transport your clients to meetings in style or let us customize a trolley tour as your guests travel between business and social destinations throughout Chicago. From black-tie events and evenings at the theater to Christmas parties and summer outings throughout Chicagoland, let Windy City Trolley lend its services to fit your needs. Our number one priority is complete customer satisfaction and showing your clients the warm hospitality Chicago offers its visitors.

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