School Trips, Class Trips, Student Performance Trips and Group Travel to Chicago, IL

I’ve always had a slight obsession with Chicago. Maybe it was all those John Hughes movies I watched growing up. Maybe it was all the road trips we took from Atlanta (where I’m from) to Milwaukee (to see family), driving through Chicago, marveling at the amazing skyline, but rarely allowed to stop. I was lucky enough to live there for six years and love to go back to visit. When I do, I love anything and everything about the city’s architecture and history.

The best way to see Chicago is on an architectural river cruise. These cruises provide a great overview and give visitors unprecedented insight into what makes Chicago such a great city. Lake Michigan frames Chicago’s eastern shore, but the Chicago River, which runs in reverse from the lake, cuts through the heart of the city, and is represented by the two blue stripes on the city’s flag.

Chicago student group travel

Our tour departs! Our guide at bottom left prepares to impart knowledge on his attentive guests.


DuSable Bridge, or the Michigan Avenue Bridge, is located at the heart of the oldest part of the city. Trump Tower (left) and the Wrigley Building (right) are in the distance.

Trump Tower is a recent addition to Chicago’s skyline.

Looking south at one of Chicago’s famed drawbridges. Willis (formerly Sears) Tower rises in the background. Willis Tower’s Skydeck is another great addition to your group itinerary!

Marina City opened in 1964. These condos feature parking garages on the bottom third of each structure.

You’ll even leave the river for a bit and venture into Lake Michigan where your cruise turns around.

The Chicago River is represented on the city’s flag by the two blue horizontal stripes.

Kaleidoscope Adventures specializes in sending student groups to Chicago. There is so much to do in this city – attractions, museums, parks, sports, shopping and regional cuisine like Chicago-style hot dogs and deep-dish pizza. With so much to do, a Chicago River cruise is the perfect way for your student group to sit back, relax, and discover this city that is second to none.