USA · CHICAGO TOURS
The architecture cruise is the one everyone gets right. These 15 compare the river boats by operator and length, then cover the observation decks, the gangster walks and the food tours worth the extra hour.
Chicago River architecture cruise with expert commentary, skyline views, pet-friendly boats, and easy downtown departures. Great value for time-limited trips.
“Guide was very knowledgeable. Easily understood. Boat was clean. Bar was well stocked. Captain very good.”
Take a 90-minute Chicago River cruise for skyline views from indoor and outdoor decks, with live narration of 130+ years of architecture.
“The architecture boat tour on the Chicago river was educational and so fun!! We did it in December 22. Yes, it was cold, but when dressed correctly, it was good! Highly recommend it!”
Chicago River 1.5-hour architecture cruise with expert guides, indoor comfort or open deck, plus a cash bar and local snacks. $44.
“The activity was very interesting. I got to know a lot about the history of Chicago as well.”
Chicago Loop gangsters and ghosts tour with a historian guide, haunted hotel stops, Cloud Gate, and an optional minibus upgrade. About 2 hours.
“Taka, with her passionate love of history, gave us a fascinating introduction to the history of Chicago. She switched easily from Al Capone and gang warfare of the prohibition era and then told of tragic loss life on the SS Eastland. So many great stories, we loved it!”
Chicago Architecture Center River Cruise on First Lady: 90 minutes of docent-led skyline views from the Chicago Riverwalk, with a bar.
“Evening was the perfect time to view the architecture along the river and Amy was a great tour guide.”
See Willis Tower from the top with timed entry, museum-style exhibits, and The Ledge glass balcony views over Chicago and farther.
“It was super fun! The museum was cool to walk through, the views were incredible and standing on the ledge was definitely a once in a lifetime experience.”
Skip the ticket line for a narrated Chicago River architecture cruise across all three branches, with 40 landmarks and bar service.
“Jeremy was a wonderfully engaging guide pointing out historical buildings, architectural styles and more as we rode the Voyageur. The boat was comfortable and not too crowded. And the staff was courteous and helpful. Great way to see the city and learn of its history while you sit back and enjoy the ride and a beverage.”
Heated coach tour of Chicago gangster sites, from St. Valentine’s Massacre to the Biograph Theatre, with photo stops and mini mob museum.
“The driver and the guide seemed to not align with where to go and stop. They went back and forth a few times and we had to walk a bit to get to a place the driver missed.”
Skip the ticket desk at 360 Chicago, ride the fast 40-second elevator to the 94th-floor deck, and enjoy skyline plus lake views.
“The view is amazing! Yes, you need some luck with the weather. I recommend to visit after 7pm in summer. You‘ll have a great view od the sunset!!”
A 45-minute Chicago River architecture cruise from the Magnificent Mile with live narration, indoor warmth, and close-up views of iconic buildings.
“The tour was very interesting and I would highly recommend. We went in early January and it was absolutely freezing. If I were doing it again I would stay in the lower climate controlled area then come out to take pictures near the end of the tour.”
Skip the ticket desk and ride fast to the 94th-floor 360 CHICAGO deck for skyline and Lake Michigan views, plus optional TILT upgrade.
“I was able to see the city view as the day light transition to dawn , I appreciate the view and took many photos.”
Live architecture narration on a 90-minute cruise from Michigan Avenue to Lake Michigan, with skyline photo views and climate-controlled seating.
“Great outing! Worth it! Our guide was very passionate about Chicago and made the trip very enjoyable.”
Family-friendly 45-minute Chicago River architecture cruise with live guide, indoor and outdoor decks, and a cash bar. Skip lines. $28.
“A great boat ride with an extremely knowledgeable tour guide. We had the best time and it was a great way to end our trip!”
Hop-on hop-off double-decker bus tour of Chicago with 24 to 72 hour passes, audio commentary, and frequent stops for parks and skyline.
“My husband and I enjoyed the big bus tour. It was very convenient in the winter with the snow. The bus was covered so you were protected from the cold and wind. Also they provided headphones so you could listen to the audio tour.”
1.5-hour Chicago Lake and River architecture cruise through the Chicago Lock, skyline views, deck or indoor seating. $44.
“Scotty D, the guide made this trip worth it. Very informative but added humor to keep it interesting. Great Chicago Skyline photo opportunity from Lake Michigan. Highly recommend!”
Every kind of day out, and the best of each.
