
Chicago by Night River and Lake Cruise
The river and then the lake after dark, with a live guide for the full 90 minutes. It boards at the stairs on Michigan and Wacker and can wait its turn at the lock.
From $50 per person
Check AvailabilityThese are the landmarks you see lit on a Chicago night, one at a time. For each you get what it is, its hours after dark, and which tour passes it. Looking at Chicago Night guided tours? Check here which landmarks your route shows you, and which you reach on foot.
Some of these you see only from the water. Others are open for you to walk into until late. Only the fountain, the Mart projection and the pier keep a timetable of their own, so check those against your evening.
Here is the short version, before the detail. "Seen from" names only what a listing's own route prints.
| Landmark | After dark | Cost | Seen from |
|---|---|---|---|
| Buckingham Fountain | Show from dusk to 11pm, in season | Free | On foot only |
| Art on theMART | Half an hour, Thursday to Sunday | Free | The Riverwalk; the 45-minute route passes the Mart |
| The Wrigley Building | Floodlit | Outside only | The sunset and 45-minute routes |
| Marina City | Lit towers on the river | Outside only | The 45-minute route |
| 360 Chicago | Open to 11pm | Paid | On foot; the sunset route passes the tower |
| Skydeck Chicago | To 10pm in summer | Paid | On foot |
| Navy Pier | To 8pm or 10pm | Free to enter | On foot |
What it is: Buckingham Fountain, one of the largest fountains in the world, in the middle of Grant Park at Columbus Dr and Congress Pkwy. It was dedicated in 1927, and its design stands for Lake Michigan.
After dark: A light, music and water show from dusk to 11pm, spring through the end of fall. It is free.
Seen from: No river cruise passes it. Go on foot or by cab before or after your cruise.
The lake cruises show the skyline end to end from the water. Compare them with the river-only sailings before you book.
What it is: Art on theMART, moving art projected across the river front of the Merchandise Mart, one of the largest digital art platforms in the world.
After dark: Half an hour a night, Thursday to Sunday. From 10 September to 27 December 2026 it plays from 7:30pm to 8pm. The 2027 dates are not out yet.
Seen from: The Riverwalk opposite. Wendella's 45-minute route passes the Mart, but no listing times its sailing to the show.
What they are: Two towers facing each other across Michigan Avenue at the north end of the bridge. The Wrigley Building, of 1920 to 1924, is clad in white glazed terracotta. Tribune Tower, 463 feet and neo-Gothic, was built to the winning design of a competition held in 1922.
After dark: The Wrigley Building is floodlit, its clock tower bright over the river. You see them both from the outside.
Seen from: Wendella's dock is beside the Wrigley Building, so its sunset cruise and its 45-minute tour start under it. First Lady's dock is across the river.
What it is: Marina City, two round towers of 65 storeys on the north bank of the river at State Street, opened in 1963 and designed by Bertrand Goldberg. A small marina sits at their foot, at river level.
After dark: The towers are apartments, so you see them from outside. At night they stand lit above the water, beside the bridges of State and Dearborn.
Seen from: Wendella's 45-minute route names it, on the main branch of the river.
What it is: 360 Chicago, the observation deck on the 94th floor of 875 N Michigan Ave, at the north end of the Magnificent Mile.
After dark: Open daily from 9am to 11pm, with last entry at 10pm. The CloudBar keeps the same hours.
Seen from: Go up on foot. The sunset cruise's route passes the tower from the water.
What it is: Skydeck Chicago, the observation deck in Willis Tower, in the Loop. It opens 365 days a year.
After dark: Summer hours run from 9am to 10pm, from 8:30am on Saturdays, with last entry 30 minutes before closing. Hours change out of season, so check them for your date.
Seen from: Go up on foot. No listing names the tower on its route.
What it is: Navy Pier, the lakefront pier east of Michigan Avenue, with the Centennial Wheel, which turns daily, lit over the water.
After dark: From 8 September to 31 December 2026 it opens to 8pm, Sunday to Thursday, and to 10pm on Friday and Saturday. Entry is free.
Seen from: The lake cruises show it from the water. The summer fireworks ended on 5 September 2026.
From the streets you see the towers from their feet. Out on Lake Michigan you see the whole skyline at once, from the pier to the towers of the Loop, lit end to end. That view exists only from a boat or from the air.
It takes a lake cruise to see it, and a lake cruise passes through the Chicago Harbor Lock at the river's mouth. First Lady's night cruise and Wendella's sunset cruise both go through. The Creepy Cruise and the 45-minute tour stay on the river.
Hours and seasons are each place's own, checked 27 September 2026. What each tour passes is its listing's own route, captured on 27 September 2026. Dates, heights and architects of the buildings are from their Wikipedia articles.

The river and then the lake after dark, with a live guide for the full 90 minutes. It boards at the stairs on Michigan and Wacker and can wait its turn at the lock.
From $50 per person
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Forty-five minutes of river architecture with a live guide, on an open deck or in the lounge. Its slots run by day, and the last of them reach dusk in summer.
From $28 per person
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About seven minutes over the skyline on the 10-mile flight, from the vertiport at 1339 S. Wood St. Fly Heli sells sunset slots; check the time you book.
From $129 per person
Check AvailabilityNext: plan the whole evening on things to do at night, choose a cruise on the night boat tours, or compare every tour on Chicago Night Tours.