Chicago · SUNSET, NIGHT & PARTY CRUISES
15 reviewed
This is the shortlist we would hand a friend: the 15 sunset, night & party cruises worth booking in Chicago, each with its price, its verdict, and the one thing to know before you commit.
Sunset cruise from the Chicago River to Lake Michigan with skyline views, warm lounge, and a full bar on a 1.5-hour Wendella ride.
“Beautiful boat ride and would highly recommend. Convenient to get to by taxi or walk from where we stayed on Monroe Street. Did get a little bumpy.”
Night views of Chicago River and Lake Michigan, plus Harbor Lock thrills, on a 1.5-hour cruise with live English narration.
“Night time lights up Chicago..left in daylight ended at night perfect”
Take a 90-minute Chicago sunset cruise on Lake Michigan via the Chicago Lock, with skyline views, onboard bar, and guaranteed boarding.
“I’m very happy and satisfied. Guide was speaking bit too fast which was hard too follow the whole speech.”
A 90-minute Chicago River architecture boat tour with guide-led stories and included coffee, tea, lemonade, water, and soft drinks for $42.
“Bery good and informative tour. I can highly recommend this tour to everybody who comes to Chicago.”
A 1.5-hour Chicago River and Lake Michigan night cruise for $45, with live narration, skyline views, and Buckingham Fountain at night.
“Beautiful sites very informative I never knew about the locking system in Chicago I would love to do it again”
A 90-minute Chicago River sunset cruise with architecture talk, an included cocktail, and views of lit-up skyscrapers plus 100-year-old bridges.
“This activity was one of my most favorite experiences of my trip to Chicago. Very cheat compared to all other activities, best money I spent during my stay! The amount of information and history that the guide new was amazing! The sunset cruise with the downtown lights was breathtaking!”
A 90-minute Chicago River cocktail cruise with live architecture narration, included drinks, and skyline views near Magnificent Mile.
“This cruise was not a cocktail cruise, it was a snooze fest. I was not accepting to learn about the architecture of Chicago. I would not recommend this cruise for anyone. This was false advertisement.”
Chicago River night cruise with gangster and horror stories at twilight, plus landmark skyline views. 1.5 hours, $45, drinks for sale.
Tiki-chic cruise from the Chicago Riverwalk through the Chicago Lock to Lake Michigan for skyline views, island music, and a full bar.
“We had a great time seeing amazing views of the city while drinking cocktails and listening to music. The staff were all very nice.”
Private 2-hour Lake Michigan sunset sail from Navy Pier with a USCG-licensed captain. Flexible route, skyline views, bring your drinks.
“We had a beautiful sunset said with Captain Mike. Wonderful city views, pleasant conversation about sailing, the City of Chicago, and our lives, with milk and chocolate chip cookies to celebrate our Dad's 80th birthday with a memorable experience for us all. Highly Recommended!”
A 90-minute Chicago River tiki-style cruise with mimosas or Bloody Marys available for purchase, skyline views, and a social, chill Sunday vibe.
“Loved it !! Got our moneys worth and great views . Nice 😊 will be going on it again . I really loved the staff and how helpful they were”
75-minute tiki bar cruise on Chicago River or Lake Michigan with skyline views, music, and a climate-controlled lounge; drinks extra. $41.
“It’s a nice ride but the bottom level smelled really bad like moldy carpet. Staff was cool and they offer an open bar option. I was also add better music if there is no tour guide.”
Moonlight kayaking on the Chicago River. See the skyline lit at night in 1.5 hours with a small-group guide and safety briefing.
“The experience was good, but I didn't feel so safe because of the different motor boats that constantly pass by.”
Pedal a BYOB cycleboat on the Chicago Riverwalk with Bluetooth tunes, built-in coolers, and skyline stops in about 90 minutes.
“Paris and Monica were dope they need a raise. My friends and I booked this boat expecting a good time and they made it an unforgettable experience.”
Tiki-themed Sunday Funday cruise from the Chicago Riverwalk with skyline views, island tunes, and onboard mimosas or Bloody Marys.
“The boatride was ok not sure I would do it again. Only one bar was open due to the low number of passengers. More communication from the crew would have been nice. The ride outside the locks was shorter expected (30min) The bartRead more”
