Processing your payment

Headout logo. Link to home.
Help

First Lady Cruises Chicago

First Lady Cruises Chicago operates a fleet of elegant boats; each with open‑air upper decks, climate‑controlled lower salons, upscale marble restrooms and a full bar. As the only official cruise partner of the Chicago Architecture Center, they deliver expert‑led river and lake sightseeing, enchanting sunset and fireworks voyages, plus fully customizable private charters for groups large or small.
4.9/5
679+ travellers from around the world love this
Headout is an authorized and trusted partner of this venue.
First Lady Cruises Chicago
Cruise boat on Chicago River passing under Clark Street Bridge.
Guide speaking on the 'Chicago First Lady' cruise with city architecture in the background.
Chicago Riverwalk with people strolling, boats on the river, and 'Chicago's First Lady' tour boat.
Guests enjoying the view on the 'Chicago First Lady' cruise.
Chicago skyline with skyscrapers and river view, Illinois, USA.
Chicago skyline with modern skyscrapers reflecting sunset colors over the river.
from
$57
Chicago River cruise boat passing under a bridge with city skyline.
Chicago River with raised lift bridges and skyline during architecture cruise.
Tour boat on Chicago River with city skyline in background during architecture cruise.
Visitors on Chicago River cruise viewing city architecture.
Chicago River with skyline view, featuring modern skyscrapers on a 45min architecture cruise.
Chicago River with skyscrapers at sunset during architecture cruise.
Chicago River with skyscrapers and bridge at sunset during architecture cruise.
Chicago River at night with open lift bridge and illuminated skyline during architecture cruise.
Free cancellation
Book now, pay later
45 min
from
$28
Cruise boat on Lake Michigan with Chicago skyline at sunset.
People enjoying a sunset cruise on Lake Michigan with a view of a lighthouse and Chicago skyline.
Chicago skyline at sunset viewed from Lake Michigan during a 90-minute scenic cruise.
Downtown Chicago skyscrapers at sunset with a cruise boat on Lake Michigan.
Cruise passengers view Chicago skyline at sunset on Lake Michigan.
Couple on deck enjoying Chicago skyline during 90-minute scenic sunset Lake Michigan cruise.
Group of friends enjoying wine on a Lake Michigan sunset cruise.
Chicago downtown skyline at sunset viewed from Lake Michigan.
Person photographing Chicago skyline during Lake Michigan sunset cruise.
Chicago skyline at sunset reflecting on Lake Michigan during a 90-minute scenic cruise.
Free cancellation
Book now, pay later
1 hr 30 min
from
$45
Chicago River architecture cruise boat passing under a lift bridge with city skyscrapers in the background.
Chicago River cruise boat with city skyline, part of 90 Min Chicago River and Lake Michigan Architecture Cruise.
Chicago River with skyline view, featuring modern skyscrapers on a 45min architecture cruise.
Chicago skyline with Willis Tower viewed from the river, featuring a raised railway bridge.
Chicago skyline with boats on the river during architecture cruise.
Tour boat on Chicago River with city skyline in background during architecture cruise.
Chicago River with skyscrapers at sunset during architecture cruise.
Free cancellation
Book now, pay later
1 hr 30 min
from
$45

Browse by themes

What our guests say

Sweta J

United States
Couple
Jan 2026


My mom is visiting Chicago for first time and taking her to the cruise and showing her the city was one of thing on my bucket list.

45-min Chicago River Architecture Cruise by Wendella

Chetna D

United States
Couple
Dec 2025



+1 more

I absolutely loved this tour! The JBL speakers were fantastic and made it so easy to hear the guide clearly, even in a busy and noisy environment. The tour guide was incredibly knowledgeable and shared information in such a fun, engaging, and effortless way that it really stayed with me. I still remember interesting facts like the Chicago River being 22 feet wide and how it turns green on St. Patrick’s Day. The clear sound from the JBL speakers and the amazing guide together made this tour truly memorable and enjoyable.

45-min Chicago River Architecture Cruise by Wendella

Kimberly E

United States
Couple
Yesterday
Our Tour Guide, Chris was great. We would totally do this cruise again. In fact, when we come back, we'll definitely do the indoor tours offered by the Chicago Architecture organization. The way Chris walked us through Chicago's history and the mindset of the architects was truly fascinating. In fact, after the tour, we were hungry and found a restaurant inside one of the buildings - The Wilco aka Corn Cob buildings. Highly recommend.

Official Chicago Architecture Cruise by First Lady

Ricardo P

Philippines
Couple
Oct 2025
The architectural tour offered a truly enlightening perspective on Chicago, its majestic skyline, historical evolution, and the vibrant energy that seems to pulse through every street and waterway. Beyond admiring the city’s striking skyscrapers and timeless facades, I was fascinated by the narrative interwoven through each structure. The Chicago River, once the city’s industrial lifeline, tells a remarkable story of transformation. From enabling trade and transport to inspiring architectural innovation, it stands as a symbol of resilience and renewal. Our guide, Cynthia, made the experience even more memorable. Her passion for Chicago was contagious, as she skillfully blended historical insights with personal anecdotes about the city’s iconic landmarks. Her storytelling brought depth and warmth to the experience, making it feel less like a tour and more like a journey through time. For a first-time visitor, this tour is a perfect introduction to Chicago’s soul—its beauty, creativity, and strength reflected not only in glass and steel but also in the stories behind them.

Official Chicago Architecture Cruise by First Lady

Suryanarayana M

Group
Oct 2025
I absolutely loved my experience on the Wendella Chicago River Architecture Cruise! The tour was both relaxing and educational, offering an incredible perspective of Chicago’s iconic skyline and its rich architectural history. Cruising through the river gave me a completely different appreciation of the city’s design — from the classic art deco buildings to the stunning modern skyscrapers. What I enjoyed the most was seeing the downtown view open up as we entered Lake Michigan — the panoramic view from the water was breathtaking. The guide was knowledgeable and engaging, making the entire journey both fun and insightful. A truly memorable Chicago experience!

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella

Terry M

Couple
Oct 2025
The view was exceptional! Wish the boat had priority boarding as an option. The boat was crowded. Overall the trip was memorable!

90-min Scenic Sunset Lake Michigan Cruise by Wendella

Nearby cities to explore

Things to do in Nashville
Things to do in Nashville
United States
Things to do in Atlanta
Things to do in Atlanta
United States
Things to do in Washington DC
Things to do in Washington DC
United States
Things to do in Philadelphia
Things to do in Philadelphia
United States
Things to do in New York
Things to do in New York
United States
Things to do in Myrtle Beach
Things to do in Myrtle Beach
United States
Things to do in Charleston
Things to do in Charleston
United States
Things to do in Savannah
Things to do in Savannah
United States
Things to do in Dallas
Things to do in Dallas
United States
Things to do in New Orleans
Things to do in New Orleans
United States

How Headout makes choosing experiences effortless

We curate the best ways to experience

We research and organise all unique experiences - from tickets to tours to special combos - so you get all the choices without the clutter.

We partner with the best

Every supplier is vetted for quality, reliability, and value so you only get top rated experiences. No surprises, no disappointments.

All the best options, in one place

Each experience is thoughtfully organised to give you maximum availability, great value and an easy way to choose.

Book with complete peace of mind

Free cancellations, Flexible payments, and 24/7 support - thoughtfully designed for flexibility, assurance, and total peace of mind.

1/4

Slide 1 of 4
We curate the best ways to experience
We partner with the best
All the best options, in one place
Book with complete peace of mind
Download app section background

We've served 49 million+ guests and we are here for you

49 million+

Happy customers across 10,000+ experiences

In the media

Featured and recommended by the best brands

24 x 7 help center

Have a question? Live chat with local experts anywhere, anytime