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Escape the Cabin Fever – 5 Ways to Enjoy Chicago in the Winter

Chicago can be a cold, long and daunting few months but it doesn’t have to be! Here are 5 ways that are sure to get you up, out and enjoying Chicago! Sledding at Soldier Field No need to wait for a snow day to sled down the 33 foot hill at Soldier Field. The Chicago […]

What to Expect on Our 2018 Chicago Holiday Tour

If you’re looking for the perfect way to get into the holiday spirit this year, look no further than the Chicago Trolley Holiday Lights Tour. You and your loved ones will love the festive tour through downtown Chicago as you hop on and off the trolley to enjoy the beautiful sights of the season. Read […]

4 Unique Ways to Spend the 2018 Holiday Season in Chicago

This holiday season, Chicago will be the perfect place to celebrate and spend time with your loved ones. Here are four unique ways to spend the 2018 holiday season in the Windy City. 1. Chicago Trolley’s Holiday Lights Tour Enjoy the spectacular lights and all the holiday splendor that downtown Chicago has to offer with […]

How to Spend Your Chicago Trip this Fall: 7 Events You Can’t Miss

There’s nothing like the autumn leaves changing in the beautiful Chicagoan parks set against the city’s skyline. The fall offers plenty of incredible events that you won’t want to miss; here are our 7 favorite events this autumn. 1. Corn Maze Outdoor Pop-Up Bar Located near Goose Island, Jack’s Pumpkin Pop-Up gives Chicagoans a unique […]

5 Ways to Spend Your Labor Day Weekend In Chicago

Labor Day marks one of the last weekends for summer family fun before the kids go back to school. Create plenty of memories for years to come by visiting Chicago for the first time – or coming back for the 100th time – to enjoy these incredible events. Here are 5 ways to spend your […]

Getting To Know You: Trolley Driver & Tour Guide, Ms. Alicia Dumas

Good News – We are are Hiring! If a typical office setting isn’t really your cup of tea, take advantage of this exciting opportunity to be a trolley driver and tour guide! That’s right, comics musicians, actors and creatives – we’re looking at you! Learn about Chicago history while we teach you to drive our […]

The 3 Tours to See Chicago (Fast!)

It’s no secret that there are plenty of beautiful attractions to see in our Windy City, but some of our favorites include tours that allow you to see many of the greatest sights at one time. Whether you are only in town for an evening or just a few days, these tours allow you to […]

Chicago Travel Tips: 8 Must-See (Unique) Locations for Your First Chicago Visit

There are plenty of must-see locations for your first visit to Chicago. With our beautiful waterfront, expansive skyline, and plenty to do, it’s easy to fill your to-do list for your first time in the Windy City. While the popular locations are non-negotiable, we love all the unique locations, holes in the wall, and fun […]

Your Wedding Trolley Rental Questions, Answered

Let’s face it, planning a wedding takes a lot of time and effort, usually calling for a large glass of vino with your besties to get through it. From photography, to accommodating guests, to who’s sitting where – every stage can be a bit stressful. The last thing you want to be worrying about on […]

The Ultimate Chicago Visit Guide: Culture & Attractions

Warmer weather has finally arrived in Chicago, which means there’s no better time to pay a visit. From award-winning museums, to historic landmarks — Chicago is rich in cultural attractions! Not to mention, booking a Hop On, Hop Off Tour makes seeing the best the city has to offer as easy as those Windy City […]