Daytime views from Willis Tower Skydeck are the more common choice, but seeing the 103rd floor and The Ledge after dark, paired with hotel pickup and an evening river cruise, is a different kind of Chicago evening.
What makes this night tour different
Instead of navigating to Willis Tower and then to a river cruise dock on your own, a small group vehicle, capped around 6 people, picks you up from your downtown hotel and handles the transfers between stops. The Skydeck visit happens at night, when the four state daytime view becomes a lit up skyline stretching toward Lake Michigan, and the evening river cruise closes out the night with over 40 illuminated landmarks narrated along the way.
What is included in this tour?
The price covers Skydeck admission including The Ledge, the evening river cruise, complimentary hotel pickup and drop off anywhere in downtown Chicago, and a narrated guided tour throughout. Tips and food or drinks are not included.
Want a closer look? Chicago Night Driving Tour with Skydeck and River Cruise, from $204 See timesIs the night driving tour with Skydeck worth the price?
It is priced higher than a daytime combo mainly because of the hotel pickup and the small group vehicle. If convenience and a nighttime view matter to you, this covers both. If you are comfortable using rideshare or walking between stops yourself, you can book Skydeck and a cruise separately for less, though you lose the narrated commentary along the way.
Short on time? Chicago Night Driving Tour with Skydeck and River Cruise, from $204 See timesWho should book this tour
Couples, small families and travelers without a car who want an easy, planned out evening get the most value here. It also suits anyone staying downtown who would rather not figure out late evening transit between Willis Tower and the riverfront on their own.
Ready to see prices? Chicago Night Driving Tour with Skydeck and River Cruise, from $204 See timesWhat to expect on the evening
Pickup happens at your downtown hotel, with exact timing confirmed in advance. The full evening runs about 3.5 hours: a short drive to Willis Tower, roughly 45 minutes at Skydeck and The Ledge, a transfer to the cruise dock and about an hour on the water, then a drive back to your hotel.
Want a closer look? Chicago Night Driving Tour with Skydeck and River Cruise, from $204 See timesPrices and what is included
This tour runs around $204 per person, including Skydeck admission, the river cruise and hotel transportation. Free cancellation applies up to 24 hours before departure, with the option to reserve now and pay later.
Short on time? Chicago Night Driving Tour with Skydeck and River Cruise, from $204 See timesGetting picked up for this tour
Hotel pickup is included anywhere in downtown Chicago. Your exact pickup window and vehicle details are confirmed after booking, so keep your phone accessible on the evening of the tour in case the driver needs to reach you.
Ready to see prices? Chicago Night Driving Tour with Skydeck and River Cruise, from $204 See timesInsider tips for the night tour
Chicago evenings can run cooler than the daytime temperature, especially on the open sections of the river cruise, so bring a light jacket even in summer. Charge your phone beforehand, since night photography of the skyline and The Ledge tends to drain batteries faster with flash and longer exposures.
Want a closer look? Chicago Night Driving Tour with Skydeck and River Cruise, from $204 See timesHow this compares to other Skydeck tours
Prefer to see Chicago during the day on foot? Book the Skydeck and river cruise walking tour instead. Just want the Skydeck view without a cruise or hotel pickup? The standard Skydeck and Ledge ticket is the most affordable option.
Short on time? Chicago Night Driving Tour with Skydeck and River Cruise, from $204 See times