Sightseeing Cruises

Chicago River & Lake Sightseeing Cruise by First Lady

4.6/5(51)

Elisabetta B

Group

Verified booking

4 days ago

The cruise is very, very well organized; the staff were punctual and professional. Above all, it is much more comprehensive than others, as it offers a view of the city from both the lake and the river. Truly spectacular. The guide on board was very knowledgeable. I highly recommend it.

Gunnar M

Couple

Verified booking

Last week

Enjoyable tour, but for non-native guests a bit hard to follow - audio guides as a service for foreigners would be recommended and could broaden the group of guests.

Sanni T

Group

Verified booking

3 weeks ago

We had dilemma accidentally while joining the cruise tour, but headout did their best and help to remove this difficulty eventually, hence we got the great experience of tour and booking service, many thanks to headout team!

Ron F

Couple

Verified booking

Aug 2026

Bartender Stephen began the onboard with a fine cocktail for me and sunblock for my tender guest. Kayley (?) presented so much history of buildings, out heads were overflowingat docking. Really liked the reference to 401 N Wabash; the blow thru floors of the 'curvy' tower, faux art decco of NBC, and many more. Reversal of the river flow and the regulating locks fascinated us. Perfect day for skyline views from the lake and Pier Two. As a 30year native of the area, my guest first time!! Grande

Jeannie M

Couple

Verified booking

Aug 2026

Evening cruise was wonderful. Sunset and no wind. We were able to go on the lake with no choppy waves. Professional crew. Matthew gave an informative narrative.

Leanne O

Group

Verified booking

Aug 2026

Seeing Chicago from a different perspective was really cool! Having the best weather ever also helped the trip go well! Seats were comfy. Staff was great!

Cruise through both the Chicago River and Lake Michigan on a 90-minute guided journey featuring panoramic skyline views, historic bridges, modern architecture, and passage through the Chicago Harbor Lock.

Listen to engaging live commentary from local guides sharing stories about Chicago’s architecture, landmarks, and history throughout the cruise.

Relax in general admission outdoor seating with access to open-air upper decks, enclosed lower salons, onboard restrooms, a full-service bar, and snack options.

Depart from the Chicago River dock with multiple sailings available from April through November, while children under 4 ride free and stroller storage is included for families.

Upgrade to skip-the-line boarding for early access and guaranteed upper deck seating with some of the best outdoor views on the cruise.

90-minute guided cruise on the Chicago River and Lake Michigan

Local guide onboard

Live commentary

Access to the open-air upper deck and enclosed lower deck

Restrooms onboard

Full-service bar and snack bar (available for purchase onboard)

Free stroller storage

Wheelchair accessible restrooms on select vessels

Children under 4 ride free

Priority boarding with skip-the-line access (as per option selected)

General boarding (as per option selected)

Food and beverages (available for purchase onboard)

Gratuities

Parking

Luggage storage

TOTAL DURATION1 hour 30 minutes
FREQUENCYApril to November, multiple departures daily
MODE OF TRANSFERBoat
1 Boarding point
Near Chicago Riverwalk, Michigan Avenue docks
Get direction
Sights covered
333 West Wacker
Merchandise Mart
Wolf Point
77 Wacker
Marina City
Trump International Hotel & Tower
Tribune Tower
NBC Tower
35 East Wacker
Aon Center
Millennium Park
St. Regis Chicago
DuSable Harbor
Chicago Harbor Lock
Navy Pier
Lake Michigan
Lake Point Tower

These tickets can't be cancelled or rescheduled.

51 reviews
How do we collect reviews?
These ratings include verified reviews from both Headout guests and our trusted partners who operate this experience locally. All reviews come from real travelers who've taken this experience.
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Guests from Switzerland, Brazil, Canada and over 9 countries have loved this experience
What our guests say
Elisabetta B
Group
Verified booking
4 days ago
The cruise is very, very well organized; the staff were punctual and professional. Above all, it is much more comprehensive than others, as it offers a view of the city from both the lake and the river. Truly spectacular. The guide on board was very knowledgeable. I highly recommend it.
Jacques R
Solo
Verified booking
2 weeks ago
The sights and tour guide was very good. The seats upstairs are just uncomfortable, cold hard steel chairs. Snacks on board quite expensive.
Sanni T
Group
Verified booking
3 weeks ago
We had dilemma accidentally while joining the cruise tour, but headout did their best and help to remove this difficulty eventually, hence we got the great experience of tour and booking service, many thanks to headout team!
Gunnar M
Couple
Verified booking
Last week
Enjoyable tour, but for non-native guests a bit hard to follow - audio guides as a service for foreigners would be recommended and could broaden the group of guests.
Terry B
Couple
Verified booking
2 weeks ago
Hailey was a great tour guide! Luis was very helpful, walking us to the correct line to get us boarded! The combo river/lake was beautiful at night.

What to bring

Bring sunglasses, a hat, or a visor to help reduce glare from the sun while viewing the buildings.

Carry a valid ID to purchase drinks at the bar.

What's not allowed

Luggage and oversized bags are not allowed onboard or at the dock, and storage facilities are not available.

Outside alcoholic drinks are not permitted on the cruise.

Pets and emotional support animals are not allowed, except for ADA-defined service dogs and all dogs participating in the Canine Cruise.

Accessibility

Wheelchair-accessible restrooms are available on select vessels, including the Classic Lady, Leading Lady, and Emerald Lady.

Guests requiring ADA access can use the ramp located at State Street and Wacker Drive within Vietnam Memorial Park, then follow the Riverwalk to the dock, as elevators are not available on the Riverwalk.

Staff assistance and early boarding are available for guests with limited mobility.

Changing tables are only available aboard the Classic Lady, Leading Lady, and Emerald Lady.

Additional information

Please arrive at least 30 minutes before departure for check-in; priority boarding starts 20 minutes before departure, and general boarding begins 15 minutes prior.

Seating is general admission, and all guests are guaranteed outdoor seating.

Cruises operate rain or shine, with an enclosed and climate-controlled lower deck available during poor weather conditions.

Children under 4 years old can ride free but must still have a ticket, and strollers must be folded and stored during the cruise.

For safety purposes, onboard restrooms close 15 minutes before the tour ends.

Discounted parking is available at 111 E. Wacker Dr. with ticket validation from the ticket office or onboard bartender.

Tickets cannot be refunded or exchanged after purchase.

The approximately 90-minute cruise passes through the Chicago Harbor Lock and features views of the city skyline and major landmarks.

Mobile tickets are accepted at the dock, so printing your ticket is not necessary.

Food and beverages are available for purchase onboard, though meals are not included with your ticket.

Your voucher will be emailed to you shortly.

Display the voucher on your mobile phone with a valid photo ID at the starting point.

Please check your final voucher for the starting point details & specific instructions.