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Things to Do in Chicago: April Edition

Chicago is one of the best cities in the country for festivals and luckily we’ve arrived at spring festival season! April offers plenty of festivals ranging in theme, age, and location so there’s something for everyone this month. Image Credit: Almost Nerdy C2E2: April 21-23 It’s back – the biggest comic book and cosplay convention […]

Pub Crawl with Chicago Trolley: Boystown

In the heart of Lakeview, the Boystown neighborhood preserves itself as a classic Chicago party scene. Catering specifically to the LGBTQ community, Boystown boasts some of the city’s most colorful and lively nightlife destinations. With Chicago Trolley transportation and a little bit of Boystown magic provided by the bars described below, you and your party […]

How To Navigate St. Patrick’s Day Festivities in Chicago

If there’s any holiday that Chicago takes seriously, it’s St. Patrick’s Day. Or rather, St. Patrick’s Day Weekend, which this year falls on March 11th and 12th, several days before actual St. Patrick’s Day holiday on the 17th. Between multiple parades, festivals, and dyeing the Chicago River green, there are countless ways to partake in […]

February Events in Chicago

Chicago winters can be rough. They can make even the most adventurous person admit defeat to a blanket and eight hours of the same TV show.  But fear not! Chicago is also known for never giving in. So when the weather gets cold, grab the family and head outside to some of the best the […]

Under-The-Radar Valentine’s Day Bar Crawl

Ah, love is in the air and Chicago Trolley is ready to take you and your valentine out for a fun and romantic night. But this isn’t just any Valentine’s Day bar crawl – we’re taking you to the hottest bars off the beaten path. This under-the-radar list is sure to impress your date! Reserve […]

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 […]