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Sightseeing Cruises

First Lady's Chicago Architecture Boat Tour

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.

Duration

1 hr 30 min

Guided tour

4.9/5

(45)

Tiffany Moreno

Tiffany

Oct 2025
Verified booking
5/5
My family of four went on the First Lady & we loved it. It is non-profit & our tour guide (From the Chicago Architecture Center) was very knowledgeable about the city's architecture & she made our tour very interesting. There are drinks for purchase (cocktails, beer & softdrinks) & the there was no bad seat in the boat. There are many options & I'm glad we chose The First Lady.
Yizhou Zhang

Yizhou

Nov 2025
Verified booking
5/5
The guide was knowledgeable and engaging, weaving history with design insight as we passed more than 40 landmark buildings. The views from the water gave a fresh perspective of Chicago’s skyline. It’s calm, scenic, and surprisingly informative—even for someone with no architectural background. Tips: bring a warm jacket (it gets breezy on the river). Highly recommended.
Amy Gazdik

Amy

Oct 2025
Verified booking
5/5
Enjoyable experience with First Lady. Everything was well organized and on time. Directions were accurate and boat was lovely and clean. Guide was knowledgeable and entertaining. Lots of enthusiasm about the he subject matter and obviously enjoys her job. A great representation for Chicago.
    • 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.

    • 90-minute guided architecture river cruise

    • Live narration by Chicago Architecture Center docents

    • Covers all three branches of the river

    • Guaranteed open-air outdoor seating

    • Full-service bar and snack bar access

    • Restrooms onboard

    • Free stroller storage

    • Limited mobility services

    • Food and drinks (available for purchase at the bar/snack bar)

    • Tips/gratuities

    • Parking (discounted parking available with validation, but not included)

    • Transportation or hotel pickup

    • Optional upgrades such as Priority Boarding Tickets (includes early boarding and CAC admission)

    • Infant tickets for children under 3 years

  • TOTAL DURATION90 minutes - 90 minutes
    FREQUENCYEvery 20-30 mins
    MODE OF TRANSFERBoat

    1 Boarding point

    112 E. Wacker Drive

    Get direction

    Sights covered

    NBC Tower

    NBC Tower

    Trump International Hotel and Tower

    Trump International Hotel and Tower

    Civic Opera House

    Civic Opera House

    Chicago Mercantile Exchange

    Chicago Mercantile Exchange

    Wrigley Building

    Wrigley Building

    Tribune Tower

    Tribune Tower

    DuSable Bridge

    DuSable Bridge

    Marina City

    Marina City

    333 Wacker Drive

    333 Wacker Drive

    Willis Tower

    Willis Tower

    Aon Center

    Aon Center

    875 North Michigan Avenue

    875 North Michigan Avenue

    Aqua Tower

    Aqua Tower

    Lake Point Tower

    Lake Point Tower

    Merchandise Mart

    Merchandise Mart

    Lyric Opera

    Lyric Opera

    The Rookery

    Carbide & Carbon Building

    Carbide & Carbon Building

    Chicago Board of Trade

    Chicago Board of Trade

    Navy Pier

    Navy Pier

    Adler Planeterium

    Adler Planeterium

    La Salle Street Bridge

    La Salle Street Bridge

  • These tickets can't be cancelled or rescheduled.

  • 4.9
    45 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.

    41
    4
    0
    0
    0
    Guests from Canada, Poland, Philippines and over 6 countries have loved this experience

    What our guests say

    Yizhou Zhang

    Yizhou

    Nov 2025
    Verified booking
    5/5
    The guide was knowledgeable and engaging, weaving history with design insight as we passed more than 40 landmark buildings. The views from the water gave a fresh perspective of Chicago’s skyline. It’s calm, scenic, and surprisingly informative—even for someone with no architectural background. Tips: bring a warm jacket (it gets breezy on the river). Highly recommended.
    Terry & Marilou Rubright

    Terry

    Nov 2025
    Verified booking
    5/5
    The tour guide was excellent. Definitely liked the history and little details of the longer tour. The day was cold for us southerners, it would be good to have prior warning about proper dress (hat and gloves). The hot toddies helped keep us warm.
    Ian Alcock

    Ian

    Nov 2025
    Verified booking
    5/5
    The all round trip was very good especially the tour guide Cheryl who was very informative.
    Kurt y

    Kurt

    Nov 2025
    Verified booking
    4/5
    Very interesting and informative tour
    Ricardo R. Palo

    Ricardo

    Oct 2025
    Verified booking
    5/5
    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.
  • Cruise all three branches of the Chicago River on a 90-minute architecture tour led by expert Chicago Architecture Center docents.

    Getting started:

    Arrive at the First Lady dock near the Chicago Architecture Center at least 30 minutes before departure for ticket validation and boarding. After a brief introduction, settle into your guaranteed open-air seat as your docent guide outlines the cruise route and key safety details.

    What to expect:

    First Lady’s Chicago Architecture Boat Tour

    This acclaimed sightseeing cruise, partnered with the Chicago Architecture Center, offers an in-depth look at the city’s renowned architectural legacy. Experience the stories behind Chicago’s iconic skyline as you travel the full length of the river.

    Features:

    • Live narration by CAC docents: Knowledgeable volunteer guides share the history, styles, and personalities that shaped Chicago’s skyline, offering insights not found in guidebooks.

    • All three river branches: The route covers the Main, North, and South branches, providing a comprehensive view of the city’s most significant buildings and bridges.

    • Open-air upper deck seating: Enjoy unobstructed sightlines of architectural highlights from the comfort of the open-air upper deck, with climate-controlled interior salons available.

    • Onboard amenities: Access a full-service bar and snack bar, well-appointed restrooms, free stroller storage, and services for guests with limited mobility.

    • Support for education: A portion of each ticket supports the educational work of the Chicago Architecture Center.

  • What to bring:

    • A hat, sunglasses, or visor to shield you from the sun as you cruise.

    • Your booking confirmation; either on your phone or printed for a smooth check-in.

    • A government-issued photo ID if staff request to verify your reservation.

    What’s not allowed:

    • Large suitcases or oversized bags; you’ll need to travel light.

    • Open strollers during boarding; please fold strollers and store them, and carry children aboard.

    • Outside food or beverages; snacks and drinks are available to purchase onboard.

    • Pets (service animals are welcome).

    • Any form of smoking, including e-cigarettes.

    Accessibility:

    • The cruise offers limited mobility services, including early boarding and river-level drop-off for guests with accessibility needs. However, full wheelchair accessibility may not be available on all vessels. Please contact staff in advance for assistance. Please reach out ahead of time so we can make arrangements.

    Additional information:

    • Plan to arrive at least 30 minutes before departure; general boarding starts 15 minutes prior.

    • Cruises run rain or shine; tickets cannot be refunded for no-shows.

    • Infants under three years old still require a paid ticket.

    • Open-air seating is guaranteed but unassigned; seating is first come, first served.

    • Well-maintained restrooms are onboard.

    • Enjoy discounted parking at 111 E. Wacker Drive; validation available at the ticket office (parking fees not included).

    • River routes may vary due to weather or city events.

    • A portion of every ticket sale supports the Chicago Architecture Center’s educational mission.

    • During major events or street closures, please allow extra travel time to reach the departure point.

    • Your voucher will be emailed to you instantly.

    • Please arrive at the boarding point 15 mins before the scheduled time of your visit to avoid any delays.

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

    Boarding point

    • Board your cruise at First Lady.

    • Address: 112 E Wacker Dr, 60601 Cook County Chicago, US.

    Get directions to the boarding point

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