Chicago · EVENING EXPERIENCES
16 tours
Chicago turns its lights on and becomes a different city, which is why so much here runs after six. These evening tours and sunset sailings cover the river, the lake and the streets after dark, with boarding times, how long each lasts and what a seat costs.
Lake Michigan sunset cruise in Chicago: ride from the Chicago River to Lake Michigan, see skyline light up, with a warm lounge and bar.
“This cruise was fun and informative. We loved that there is a bar and snacks. Although it was a sunset cruise and the sun was not out, the city lights view was nice.”
Glide from the Chicago River to Lake Michigan at night, passing through the harbor lock for skyline views and live guide storytelling.
“My Guide was very knowledgeable about Chicago History. What he was saying didn't sound Like he was reading a Script. I was surprised We Had a lot in common!? The Experience is something I WILL Definitely recommend to my Family, Friends, and anyone else who I can express any interest in learning about Chicago.”
Sunset over Lake Michigan with skyline views, a Chicago Locks passage, and an onboard cash bar. 90 minutes, $45 per person.
“Absolutely amazing time!! Did it during Covid and still has an absolute blast. Even better then normal the staff told us. Great attention to deal and will definitely recommend”
Chicago Night Crimes bus tour with live narration, gangster stops like the St. Valentine’s Day Massacre, and a finale near the Water Tower.
“This tour was very informative, professional and humorous. Began on time and ended with a nice surprise. Highly recommend to anyone wanting some back stories about the Chicago mob history.”
1.5-hour night cruise on Chicago River and Lake Michigan with live guide talks, skyline lights, and Buckingham Fountain views.
“Beautiful sites very informative I never knew about the locking system in Chicago I would love to do it again”
Sip a cocktail while an award-winning guide explains Chicago River architecture, from historic towers to lit skyline at dusk.
“I had a great experience, the staff was friendly and the tour guide was very informative, I learned a lot of interesting facts about the buildings and had a good time sightseeing with a drink in my hand. 5 out of 5 stars”
See Chicago after dark from an open-top double-decker bus, with live English or Spanish commentary and photo-friendly night views.
“Bug bus broke before we left We had to cancel. Big bus should have another bus to replace it and have the excursion, not cancel it.”
A 2-hour Chicago night crime tour by luxury bus, from the St. Valentine’s massacre site to John Dillinger’s final steps and mob artifacts.
“These guys were very knowledgeable about the crime history of Chicago. Very Friendly and extremely funny tour guides. Very nice experience. Must do!!”
90-minute Chicago sunset skyline tour on an open-top double-decker bus with a live guide, Lake Michigan views, Millennium Park, and Art on the Mart.
“Not very excited, definetely overpriced, the tour guide was not respectful. Also forgot an expensive scarf on the bus, the stuff even did not try to locate me although the guide asked me where I was from, what hotel I was staying in and what conference I have attended.”
A 1.5-hour Chicago River night cruise with darker stories, mob-era tales, and skyline views around famous downtown landmarks for $45.
A small-group Chicago night tour with Willis Tower Skydeck, skip-the-line entry, and a shoreline cruise past 40 landmarks from downtown.
“Organisation désastreuse. Visite prévue de la rivière chicago annulée car le guide s est trompé. Remplace par 1 visite sur le lac non programmé fait en dernier minute et sur 1 créneau horaire en dehors du créneau horaire prévu. Des allés retours pour pallier cette incompétence et cette désorganisation qui nous ont fait perdre notre soirée.”
Private 2-hour sunset sail from Navy Pier with a Coast Guard captain, flexible route, and skyline views over Lake Michigan.
“Cpt. Mike took us out in his boat for sunset, it was fantastic and very relaxed. I would highly recommend him and willl definitely do this again when we have our next visitors to Chicago.”
Small-group Chicago night tour for $189: Willis Tower Skydeck, a 40-min after-dark river cruise, and Cloud Gate plus skyline views.
“We had Omar (who was training) and Andrew. Andrew was amazing so knowledgeable of the history and architecture so much of the city we would never have even known about or thought of,industry of the past and present here in Chicago You will not be disappointed. Willis Tower is beautiful and breathtaking at night!”
A beginner friendly Segway sunset tour of downtown Chicago, with hands on training and photo stops at top landmarks for $75.
“Great tour guide.very knowledgeable . Beautiful lakeside tour!!! Buckingham fountain was breath taking! Marty”
Ride a Segway across Chicago at night, hit Millennium Park, watch Buckingham Fountain, then catch Navy Pier fireworks over Lake Michigan.
“Increíble experiencia! El tour muy divertido. Las vistas muy lindas. Nuestro guía Sean espectacular! Valió la pena muchísimo!”
