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Pub Crawl With Chicago Trolley: Bridgeport

Bridgeport is a South Side neighborhood with lots of old-school Chicago charm – meaning it’s perfect for knocking back a couple of brewskies in bars that are like diamonds in the rough. Gather your friends and reserve your trolley now for your big night out in this South Side haven. Stop One: The Duck Inn […]

Tie the Knot with Chicago Trolley

The cake has been delivered, the flowers have been delicately placed, and your loved ones are gathering to celebrate you and the love of your life. It’s your wedding day, and all that’s left to do is a) actually get married and b) let an elegant Chicago Trolley carry you from place to place. Classically […]

Holiday Pub Crawl Spots

The Yuletide season brings a very specific set of flavors that are a treat to taste. Luckily, Chicago is full of bars that truly deliver in holiday drinks. Plan a holiday pub crawl with these bars that serve gloggs, eggnogs, and more! And don’t forget about the transportation – Chicago Trolley & Double Decker can […]

12 Holiday Events in Chicago

Chicago miraculously transforms into a winter wonderland right around the holiday season. Lights are hung and illuminate joy in our city streets, seasonal goodies fill our stomachs with warmth, and events charm our locals and visitors alike. Despite the cold temperatures outside, it is a time to radiate of holiday happiness and partake in the […]

5 Reasons to Visit Chicago During the Holiday Season

The holiday season is truly a wonderful and magical time of the year in Chicago. Whether you’re traveling with your special someone or the whole family, there’s plenty to do and see in our beautiful city. Here are 5 reasons to visit Chicago during the holiday season. 1. Skating Ribbon in Maggie Daley Park When […]

How to See Chicago the Way the Locals See It

Whether you’re brand new and just moved to a city or simply visiting, it’s easy to find and see the touristy areas. (After all, they are the ones most publicly advertised.) But many of us enjoy finding the holes in the wall – the places that only locals visit – to get a true sense […]

Pub Crawl with Chicago Trolley: Pilsen

After coming off a long holiday weekend, we know the perfect thing to get perk you up: planning a pub crawl with Chicago Trolley. This week, let’s explore Pilsen, the awesome and sometimes-forgotten jewel of Chicago’s nightlife neighborhoods. Go ahead and reserve your trolley now for your big night out, and in the meantime, feel […]

3 Family Friendly Activities & Things To Do in Chicago This Winter

There’s nothing quite like Chicago in the winter. You can feel the crisp chill in the air, smell the wood burning in fireplaces keeping homes warm, and hear the snow crunch beneath your feet as you walk along the street. The start of winter means the holidays are just around the corner; making it the […]

8 Chicago Holiday Attractions You Won’t Want to Miss

Chicago is one of the most picturesque cities for the holidays. There’s snow, lights, horse-drawn carriages, caroling — a little bit of magic for the whole family. Unsure where to start with your December festivities in this jewel of a city? Here’s a helpful guide that makes the most of everything Chicago has to offer […]

Chicago Trolley Pub Crawl: Andersonville

Andersonville might not be the same sleepy neighborhood occupied by Swedish immigrants that it used to be, but it has never sacrificed its charm. Amid a city with rapidly changing neighborhoods, the North Side area still feels cozy and welcoming, albeit with a modernized flair. It’s all what makes Andersonville the perfect destination for a […]