Processing your payment

Headout logo. Link to home.
Help
#8 out of 14 in Chicago

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.

4.8/5

580+ travellers love this

Read our recent reviews

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.
1 hr 30 min
  • Glide along all three branches on a 90-minute architecture cruise led by Chicago Architecture Center docents, who share insider stories of the city’s iconic skyline and riverside landmarks.

  • Guaranteed open-air seating ensures uninterrupted views of historic skyscrapers, modern marvels, and architectural treasures while your volunteer guide brings each structure’s narrative to life.

  • Enjoy onboard comforts; restrooms, free stroller storage, and dedicated accessibility services, while treating yourself to craft beverages and tasty bites available at the full-service bar and snack station.

  • Rain-or-shine departures mean you’ll witness Chicago’s architectural beauty in every season, and discounted nearby parking makes it easy to arrive and embark on your adventure stress-free.

  • A portion of your ticket supports the educational work of the Chicago Architecture Center.

More details

  • Glide along all three branches on a 90-minute architecture cruise led by Chicago Architecture Center docents, who share insider stories of the city’s iconic skyline and riverside landmarks.

  • Guaranteed open-air seating ensures uninterrupted views of historic skyscrapers, modern marvels, and architectural treasures while your volunteer guide brings each structure’s narrative to life.

  • Enjoy onboard comforts; restrooms, free stroller storage, and dedicated accessibility services, while treating yourself to craft beverages and tasty bites available at the full-service bar and snack station.

  • Rain-or-shine departures mean you’ll witness Chicago’s architectural beauty in every season, and discounted nearby parking makes it easy to arrive and embark on your adventure stress-free.

  • A portion of your ticket supports the educational work of the Chicago Architecture Center.

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.
Sightseeing Cruises
Free cancellation
Book now, pay later
45 min
  • Sail through the heart of Chicago on 45-min guided architecture cruise, enjoying expert commentary, gorgeous skyline views, and onboard refreshments.

  • Glide along all three branches of the Chicago River including the North Branch, the Main Stem, and the South Branch, as your guide shares fascinating insights into the city's 130-year architectural evolution.

  • Capture unobstructed views of Chicago’s iconic skyscrapers from the open-air upper deck, offering perfect photo opportunities of the cityscape.

  • Spot famous buildings like the Tribune Tower, Apple Store, AMA Building and the Wrigley Building.

More details

  • Sail through the heart of Chicago on 45-min guided architecture cruise, enjoying expert commentary, gorgeous skyline views, and onboard refreshments.

  • Glide along all three branches of the Chicago River including the North Branch, the Main Stem, and the South Branch, as your guide shares fascinating insights into the city's 130-year architectural evolution.

  • Capture unobstructed views of Chicago’s iconic skyscrapers from the open-air upper deck, offering perfect photo opportunities of the cityscape.

  • Spot famous buildings like the Tribune Tower, Apple Store, AMA Building and the Wrigley Building.

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
  • Unwind on a 90-min scenic cruise and enjoy the golden hues of Chicago’s skyline reflecting from the waters of Lake Michigan and Chicago River.

  • Your premium boat features open-air decks and a climate-controlled cabin for year-round comfort.

  • Enjoy a relaxing experience with light narration that shares interesting insights as you sail past Chicago’s architectural icons.

  • Catch golden hour from the water — this evening cruise offers a romantic and peaceful way to end your day in Chicago.

More details

  • Unwind on a 90-min scenic cruise and enjoy the golden hues of Chicago’s skyline reflecting from the waters of Lake Michigan and Chicago River.

  • Your premium boat features open-air decks and a climate-controlled cabin for year-round comfort.

  • Enjoy a relaxing experience with light narration that shares interesting insights as you sail past Chicago’s architectural icons.

  • Catch golden hour from the water — this evening cruise offers a romantic and peaceful way to end your day in Chicago.

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
  • Enjoy a 90-min guided boat tour on the Chicago River and one of the five Great Lakes, Lake Michigan, with skip-the-line entry.

  • Take in the city’s famous skyline and architectural icons from both the river and lake while relaxing indoors or on open-air decks.

  • Learn how Chicago’s skyline came to life with engaging narration as you cruise past historic buildings and modern skyscrapers.

  • This extended cruise offers more than standard river tours, covering additional landmarks and panoramic lakefront city views.

  • Perfect for first-time visitors, architecture buffs, and photography enthusiasts looking to explore Chicago from a different perspective."

More details

  • Enjoy a 90-min guided boat tour on the Chicago River and one of the five Great Lakes, Lake Michigan, with skip-the-line entry.

  • Take in the city’s famous skyline and architectural icons from both the river and lake while relaxing indoors or on open-air decks.

  • Learn how Chicago’s skyline came to life with engaging narration as you cruise past historic buildings and modern skyscrapers.

  • This extended cruise offers more than standard river tours, covering additional landmarks and panoramic lakefront city views.

  • Perfect for first-time visitors, architecture buffs, and photography enthusiasts looking to explore Chicago from a different perspective."

from
$45

What our guests say

Sweta Joshi
US

Sweta

United States
Jan 2026

review-image

review-image
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

Chetna Dhembla
US

Chetna

United States
Dec 2025

review-image

review-image

review-image

+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

Ricardo R. Palo
PH

Ricardo

Philippines
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.

First Lady's Chicago Architecture Boat Tour

Jon Voegele
US

Jon

United States
Oct 2025
It was an absolutely great day on the river! The tour, the guide, the employees were all exceptional! We brought friends from Seattle and they loved the tour as a favorite of their Chicago visit! Kudos!!

First Lady's Chicago Architecture Boat Tour

Suryanarayana Murthy Majji

Suryanarayana

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

Elia Martinez
US

Elia

United States
Sep 2025
We have taken this cruise many times, we take family and friends when they visit. We always learn something new. Our tour guide Kenny was amazing. Funny, amiable and very informative. Kudos!!

90-min Chicago River and Lake Michigan Architecture Cruise

Terry moore

Terry

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

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

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 47 million+ guests and we are here for you

47 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