Header Image

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 […]

7 Ideas for a Family-Friendly Spring Break

Chicago is a beautiful place for families to spend spring break! In a city rich with culture, museums, parks, music and more, there’s never a shortage of happenings to explore.   The Art Institute of Chicago The Art Institute of Chicago features ancient art from around the world, renaissance paintings, carved furniture from bygone eras […]

Top Four Events in Chicago This March

After a snowy winter, Chicago is finally starting to warm up! The days are longer, the trees are budding, and Chicagoans are emerging from hibernation ready to have some fun. If you’re thinking of planning a trip to the Windy City this month, there are a ton of festivals and events for you to experience. […]