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

991 travellers from around the world love this

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.

Official Chicago Architecture Cruise by First Lady

1 hr 30 min

Meals included

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.

45-min Chicago River Architecture Cruise by Wendella

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.

90-min Scenic Sunset Lake Michigan Cruise by Wendella

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 skyline with Willis Tower viewed from the river, featuring a raised railway bridge.

Chicago skyline with boats on the river during architecture cruise.

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

Free cancellation

Book now, pay later

1 hr 30 min

from

$45

Similar things to do in Chicago

Tour boat on the Chicago River with downtown Chicago skyscrapers in the background.

Wendella Cruises Chicagofrom $28

Boats and kayaks on the Chicago River with city skyscrapers in the background.

Chicago River Architecture Cruise Ticketsfrom $32.50

People on a boat deck viewing Chicago skyline at dusk with water and cloudy sky.

Shoreline Cruises Chicagofrom $32.50

Family enjoying the view from 360 Chicago observation deck.

360 Chicagofrom $30

Couple lying on glass ledge at SkyDeck, Willis Tower, overlooking Chicago skyline.

Willis Tower Skydeck Ticketsfrom $42.33

Open-top Big Bus Chicago tour in downtown with skyscrapers in the background.

Big Bus Chicago Hop-on Hop-off Toursfrom $49

Chicago Architecture Center facade with city reflections and pedestrians.

Chicago Architecture Centerfrom $7

Browse by themes

Museums in Chicago

Chicago City Cards

Landmarks in Chicago

Observation Decks in Chicago

View all Chicago Attractions

Guided Tours in Chicago

Hop-on Hop-off Tours Chicago

View all Chicago Tours

Airport Transfers in Chicago

Public Transport Tickets in Chicago

Shared Airport Transfers

View all Transportation in Chicago

Sightseeing Cruises in Chicago

Dinner Cruises in Chicago

Lunch Cruises in Chicago

View all Cruises in Chicago

Combos Tickets in Chicago

View all Chicago Specials

What our guests say

Anuj M

Canada

Couple

Last week

+4 more

That's absolutely great experience with Wendella Tours & Cruises. They've explained very well throughout the ride. Thank you for making our trip remarkable.

45-min Chicago River Architecture Cruise by Wendella

Jazmine M

United States

Couple

2 weeks ago

+2 more

Spent my last day in Chicago with Jake and the Wendella team. The 45 minute tour truly superseded my expectations! I'm the last person that you would call a history buff, but I found myself mesmerized by how the city's taken shape over hundreds of years. Jake is truly an outstanding guide who loves what he does. He offered so much insight on the city's archeitrcture, changing landscapes, whimsical lore, and offered so many recommendations on food and nightlife in the city.

45-min Chicago River Architecture Cruise by Wendella

Matias S

Argentina

Solo

Last week

The great exposition of yours tourist guide, amazing, funny and very interesting. The length was perfect and the places incredibles. A must do in Chicago.

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

Marlene W

United States

Couple

3 weeks ago

Anyone who visits Chicago should definietly take this cruise. What a beautiful city and the diversivied architure is spectacular. Our guide gave us a detailed history of so many of the buildings. He was amazing and it was fasinating to hear what a transformation Chicago and the Chicago went through, from dead livestock to a beautiful river and riverwalk. 5 star recommendation!

Official Chicago Architecture Cruise by First Lady

Martina G

Group

Apr 2026

Our guide was very informative and it was great to see the city from the river which gives a completely different perspective to the buildings and the layout. Would highly recommend First Lady architecture tours

Official Chicago Architecture Cruise by First Lady

Justin B

Solo

Last week

Honestly the cruise was great but the guide Scotty D was incredible. He was fun, knowledgeable, and engaging. The cruise was a good mix of architecture and lake views, timely, and comfortable.

90-min Scenic Sunset Lake Michigan Cruise by Wendella

Lou H

United States

Solo

Last week

I was looking for just what I got. A pleasant ride out onto the lake with the sunset view of Chicago, a welcoming MC and nice people to talk with. The only thing I might say is that the boarding location was very confusing because they have two docks that are not easy to move between, but the cruise itself was lovely. Enjoyed going through the locks too.

90-min Scenic Sunset Lake Michigan Cruise by Wendella