The most iconic summer event in Chicago is to spend time on on a boat cruise on Lake Michigan or along the Chicago River. The skyline views they offer are popular with locals, visitors, event planners and business travelers.

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For more than 75 years (third generation of family ownership), Shoreline Sightseeing has been showcasing that skyline — now with 10 touring vessels and even nine water taxis. And they offer a much more unique view of the city than you get on the streets.

Shoreline has three primary docks for  tours: one is along Navy Pier itself, one is at Navy Pier’s Polk Brothers Park (southwest corner) and at the third is at the Michigan Avenue Bridge (enter at the northeast corner of the street and walk to the lower level).

Options include architectural tours, classic lake tours, fireworks tours, special events, group programs and charters. If you are an event planner or a business traveler new to Shoreline Sightseeing and boat tours in general, you should consider taking of the following tours:

Shoreline Architecture Boat Tours

Chicago is known for its architecture, and Shoreline’s expert guides share their insights into the buildings alongs the way — including the Tribune Tower, Wrigley Building, Trump Tower Marina City and many other landmarks.

The Chicago architecture tour is 75-minues and runs along the Chicago River. You can catch it at Navy Pier’s Polk Brother’s Park and at the Michigan Avenue Bridge.

Rob and I took the tour from the Michigan Avenue location at 10 a.m. on a Saturday morning, which is a great time of day from a weather perspective. It travels along the river and turns at the North Branch, going as far north as the Grand Avenue Bridge before turnaround around and traveling south past Rivercity Condominiums.

It’s good to arrive early, but even if you arrive just prior to departure, there’s a good chance they have enough seats for everyone to have great views on the upper deck (that was our experience).

John, our local docent who has been with Shoreline since 2008, provided expert insights on the buildings, their history, local trivia and even the spots where you can get the best photos. Being locals, even we were surprised at how much we learned.

The boat had a fully stocked bar — complete with alcoholic and non alcoholic beverages. We could not think of a more relaxing 75 minute way of spending a beautiful Saturday morning than on the River cruise.

Shoreline Fireworks Display Boat Tours

Each Wednesday and Saturday night between Memorial Day and Labor Day (and at other special occasions), Chicago holds a fireworks display from Navy Pier. It’s great to watch from a spot along the pier, but it’s spectacular when you watch it from a water view.

Shoreline has two options:

    1. The architecture fireworks tour is 90-minutes and departs from both locations at 8:30 p.m. It includes a review of the three branches of the river and concludes with a lake fireworks view.
    2. The lake fireworks tour is 60-minutes and only departs at 9:30 p.m. from the the Navy Pier location.

The lake fireworks tour is picturesque. A personal guest of mine and I took the 9:30 p.m. tour which sailed as far south as the Museum Campus before turning back to Navy Pier for the show.

I recommend arriving 20-30 minutes early to get a great seat in the top-back, although the boat will essentially make a circular route so everyone gets at least 30-minutes of a skyline view. You will be surprised at how different the skyline appears from the Lake perspective, as well as learning about the integral part which the Lake plays in Chicago history.

The tour did not include a personal docent explaining the sites; however, it does have a prerecorded overview of the skyline from the view of the lake.

Shoreline Special Event Boat Tours

Shoreline Chicago takes its architecture and classic lake tours and creates themed special events, such as wine tasting cruises, ribs on the river cruise, holiday fireworks cruises (e.g., the St. Patrick’s Day, Fourth of July and Oktoberfest), hard cider tasting and a monthly brew cruise.

Rob and a personal guest took one of the summer brew cruises with Revolution Brewing. This was a 90-minute architecture cruise that typically includes the lake along with the three branches of the Chicago River. However, weather was still cool and windy on the night when Rob signed up as it was scheduled in May, and you cannot always count on Chicago weather in May, so Shoreline expanded its time on the river which was perfectly fine.

The brew cruises showcases a sampling of four of Revolution Brewing’s craft beers (12 oz cups). There’s a DJ who plays music on the upper deck and the bar is stocked down below — along with appetizers and other snacks (you can find the bulk of the food at the front of the boat down of the lower deck).

Shoreline bartenders Tommy Czepiel (8 years) and Amber Stevenson (2nd season) were great ambassadors for the microbrew, and everyone was in a great mood on board.

Shoreline for Charters and Groups in Chicago

Event planners interested in organizing corporate events, fundraisers and private celebrations on the lake, Shoreline has a two special vessels in its fleet: the Celebration (which has a capacity to hold 100 passengers reception style and 72 passengers for a seated event), and the Evening Star (which has the capacity to hold 70-200 passengers reception style and various seating capacities based on configuration.

The options allow for a duration of two to three hours, depending on your needs. For more information, email or call 312-373-7256.

Have you experienced a Chicago Shoreline Sightseeing cruise? Share your experience with us.

— Rob Hard also contributed to this review.