Shoreline Sightseeing

Shoreline Sightseeing: The Best Way to See Chicago by Water

Our Chicago, the Windy City, is renowned for its city skyline, world famous architecture, and Scenic Ocean like waterfront along Lake Michigan.

Like I wrote about all possible ways to enjoy what our city has to offer, I would say taking one of the boat tours with Shoreline Sightseeing is also a one experience that truly stands out among the rest.

Whether you’re a first-time Chicago visitor or a lifelong local like me, taking a Shoreline Sightseeing tour offers one of the best ways to experience the city from its waterways.

In this guide, I’ll dive into everything you need to know about Shoreline Sightseeing from its famous architecture tours to fireworks cruises, what to expect on boat, why it’s worth the ticket, and tips for getting the most out of your sailing.

What Is Shoreline Sightseeing?

Shoreline Sightseeing is one of Chicago’s oldest and most beloved boat tour companies. It is offering boat cruises and water taxi services since 1939.

Yes, this company has been around nearly a century and over these years Shoreline has become synonymous with high-quality, informative, and scenic boat tours along the Chicago River and Lake Michigan.

Their popular architecture tours, skyline lake tours, and special event cruises draw hundreds of thousands of passengers every year.

Whether you’re interested in Chicago’s architectural history or simply want a beautiful view of the city believe me Shoreline has a cruise for you.

Book a Shoreline Sightseeing Architecture Cruise on Viator – Check availability and prices here

Top Shoreline Sightseeing Tours

1. Architecture River Tour

I highly recommend this tour. If you only do one tour in Chicago, make it this one. The Architecture River Tour is Shoreline Sightseeing’s popular tour.

This 75 minutes long boat tour is led by expert docents. It will take you through all three branches of the Chicago River where you can get up-close views of over 40 iconic buildings.

You’ll hear fascinating stories behind landmarks like the Willis Tower, Wrigley Building, Tribune Tower, Marina City, and Aqua Tower.

These tours don’t just point out pretty buildings but they get into the styles, designers, and historical context that shaped Chicago’s skyline.

Pro Tip: I recommend to book this tour during golden hour for stunning light and unforgettable photos.

Included with the Go City Chicago Pass – Grab your pass here

2. Skyline Lake Tour

Want sweeping views of the skyline? The Skyline Lake Tour is a 40-minute cruise along Lake Michigan that departs from Navy Pier.

It’s shorter and more casual than the architecture tour but delivers postcard-perfect views of the city’s most famous buildings from the lakefront.

In my opinion this tour is perfect for families with young kids or anyone who has very short time to explore Chicago.

You can enjoy a laid-back ride, grab a drink on board, and capture panoramic shots of Chicago from the water.

3. Fireworks Cruises

Navy Pier fireworks starts during summer. Like other boat tour companies, Shoreline Sightseeing also offers Fireworks Cruises that align with Navy Pier’s weekly fireworks shows.

These tours offer a front-row seat to one of Chicago’s most loved traditions. The reflection of the fireworks off the lake combined with the skyline view makes a memorable sailing at night.

Fireworks cruises are available on both the river and the lake and often sell out, so I recommend to book early.

Reserve your fireworks cruise on Viator – Book now

4. Water Taxi Service

Looking for a fun and affordable way to get around the city? Shoreline also runs a convenient Water Taxi service that connects popular destinations like Union Station, Willis Tower, Michigan Avenue, Museum Campus, and Navy Pier.

It’s a scenic alternative to traditional public transportation and a relaxing way to beat Chicago traffic.

Why Shoreline Sightseeing Stands Out

You must be thinking there are several boat tour companies in Chicago, so why choose Shoreline?

Knowledgeable Tour Guides

Shoreline’s guides are among the most well-trained and passionate in the business. Their architecture tours, in particular, are known for being rich in detail, engaging, and even a bit humorous. They turn a sightseeing tour into a storytelling experience.

Frequent Departures

Tours run frequently throughout the day. Especially during the warmer months (April to October) they have higher frequency. This makes it easy to fit a tour into any itinerary.

Multiple Locations

Shoreline has docks at Navy Pier and Michigan Avenue. I feel that having docks at multiple locations makes it super convenient no matter where you’re staying or exploring in the city.

Family-Friendly Fun

All tours are family-friendly and kids under three typically ride free. Many boats offer snacks and drinks on board, making for a comfortable ride for the whole crew.

What to Expect on a Shoreline Sightseeing Tour

• Comfortable Seating: Most boats offer open-air top decks and shaded seating below. You’ll have great views from anywhere on board.
• Photo Opportunities: Bring your camera or smartphone. The skyline, bridges, and historical landmarks offer endless photo ops.
  
  Quick Tip: Keep your portable phone charger as you do not want to miss opportunity to capture any view.
  
• Live Commentary: The narration is live and interactive, not a boring pre-recorded loop.
• Bathrooms and Snacks: Most larger boats have restrooms and onboard concessions available.

Best Times for Tour

Morning: Less crowded and cooler, perfect for a peaceful ride and clear photos.

Golden Hour/Sunset: Stunning lighting and unbeatable views. Ideal for romantic outings or photo lovers.

Evenings (Fireworks Nights): For a special night out, nothing beats cruising under a starry sky with fireworks above.

Ticket Info and Booking Tips

• Prices: Range from $30–$50 for adults depending on the tour type. Kids’ tickets are discounted.
• Discounts: Check Chicago attraction passes such as Go City Chicago Pass, or Chicago CityPASS for bundled savings.
• Online Booking: Personally I highly recommended to book online. Book in advance especially in summer and on weekends. Also, Viator offers discounted tours deals.

Nearby Attractions

Before or after your tour you can take advantage of being close to top Chicago attractions:

• Navy Pier: Enjoy Shops, restaurants, the Centennial Wheel, and live entertainment.
• Millennium Park: Home to The Bean, Crown Fountain, and summer concerts.
• Maggie Daley Park: Great for families with kids. It features playgrounds, mini-golf, skating.
• Chicago Riverwalk: My favorite spot as well. Perfect for a stroll, dining, and to relax along the scenic riverside promenade.

Overall, whether you’re a tourist or a local looking to see Chicago in a new light, Shoreline Sightseeing is an experience that delivers every time. It’s educational, relaxing, and packed with some of the best views the city has to offer.

Ready to cruise Chicago in style?

Book your Shoreline Sightseeing tour online and set sail for one of the most unforgettable experiences in the Windy City!

🎟️ Compare all Shoreline tours on Viator

🏙️ Save big with a Go City Pass and City PASS Chicago.

🛎️ Book nearby hotels on Expedia