Chicago · EVENING EXPERIENCES
Good evening experiences fill up weeks ahead; the great ones go first. Below: the 15 to book early, what each includes and how they differ.
A 90-minute Chicago sunset cruise from the Magnificent Mile to Lake Michigan, with skyline lights, on-board bar, and expert narration.
“Beautiful views of the Chicago skyline at all stages of the sunset. Our tour guide (Stevie B?) was energetic and even took photos of us on the boat. He went above and beyond. I would definitely take this ride again, must see views of the city!”
Chicago by Night River and Lake cruise at night, guided skyline views plus a real ride through the Chicago Harbor Lock system.
“We had 1 night in Chicago and thia trip was the the best was to get the most out of the city by night... this was an amazing experience, it's just a shame we were only there for 1 night... we will definitely be back again and this will definitely be on the list again”
A 1.5-hour Chicago sunset cruise with the Chicago Lock transfer, skyline views over Lake Michigan, and a cash bar with local favorites.
“A must do. Such breathtaking views and so fun. Our tour guide, Kay (my apologies if mis-spelled), was fantastic. Aside from the knowledge she shared, she made the experience personable by going around to everyone. My boyfriend and I had a great conversation with her. An absolute gem.”
Chicago Night Crimes bus tour with live gangster storytelling, photo stops at famous sites, and brief visits including Biograph Theatre and Nitti’s Vault.
“Great tour. Our guide was awesome and his knowledge of the subject was second to none! If you are a mobster enthusiast, you have to do this tour!”
Chicago skyline at night on a 1.5-hour cruise of the river and Lake Michigan, with live guide commentary and bright Buckingham Fountain views.
“Seamus was fantastic. He was a great guide with a relaxed, funny manner that really made the tour enjoyable. Bar staff were super friendly.”
Sunset cocktail cruise on the Chicago River with award-winning docents. See 50+ buildings, 100-year bridges, and city lights in 90 minutes.
“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’s skyline lit up on an open-top sunset bus with a live guide in English or Spanish, plus great photo stops.
“Excellent way to see Chicago…the guide was humorous, knowledgeable and extremely informative. It was definitely a great experience.”
Chicago Crimes Night Tour is a 2-hour bus ride with live storytelling, St. Valentine's Massacre stops, Dillinger walking path, and a mob museum.
“According to my two teenage boys, this was the best part of their first visit to Chicago.”
Ride an open-top double-decker on Chicago’s sunset skyline loop, with a live guide and big views from Museum Campus to Millennium Park.
“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 spooky gangster tales, Eastland and Chicago Fire stories, plus skyline views from Tribune to Willis.
A small-group Chicago night tour with Willis Tower Skydeck and an evening skyline cruise, plus hotel pickup and Cloud Gate views.
“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 Lake Michigan sunset sail from Navy Pier with a licensed captain, flexible routes, and skyline views you cannot get from shore.
“Mike was awesome! It was my first time on a private sail with friends. We were comfortable, the sail was smooth and we had a great time. We didn’t want it to end.”
Chicago sunset Segway tour past Lake Michigan landmarks and downtown icons, with hands-on coaching, helmets, and a small-group ride.
“I love Segway tours! This tour took us down by Lake Michigan and got to see the Chicago skyline at sunset. Went by some fountains and other great picture opportunities.”
Small-group Chicago night tour with Skydeck Willis Tower, an after-dark river cruise, and skyline photo stops, plus downtown pickup.
“Ruben was excellent! So knowledgeable of the area, good sense of humor & very kind! Thank you Ruben for making my last night in Chicago 👌🏽”
Glide Chicago at night on a segway, then watch Navy Pier fireworks with big views of Buckingham Fountain and Millennium Park.
“Increíble experiencia! El tour muy divertido. Las vistas muy lindas. Nuestro guía Sean espectacular! Valió la pena muchísimo!”
Every kind of day out in the city, and the best of each.
