If you’ve only spent a few short days in Chicago, you might have missed out on some of its cooler sites and attractions.
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From architecture to pro sports to rooftop bars, there’s a lot to uncover in Chicago. In fact, you might find your itinerary filling up faster than expected if you really dig into its hidden gems. There are secret jewelry stores, plenty of tucked-away speakeasies, and more than a few natural oases to enjoy when the weather warms up.
Regardless of what’s on the docket, I have one tip: Get out on the water, either on the Chicago River or Lake Michigan. Taking a little boat tour is one of the best ways to see a large city’s skyline, and, if you’re like me, you don’t often have the chance to sail or cruise.
If that’s the case, these are the river tours in Chicago that I recommend booking, including Lake Michigan tours. There’s something for everyone, whether you like tiki parties, historical fireboats, or sunset sails.
River tours in Chicago: booze cruises, history, and more
- Premier Plus Brunch Cruise on the Chicago River from City Cruises Chicago: Enjoy an upscale brunch while cruising past the city’s most famous architectural monuments. Along the way, your meal will be accompanied by casual commentary and bottomless mimosas.
- Chicago River Sunday Funday Booze Cruise from Island Party Boat: If you’re more focused on bottomless drinks than taking in the city’s top sights, this Sunday cruise is for you. Food and drinks are available for purchase at the cash bar. Expect lively tunes, as well.
- Chicago Skyline Tiki Chic Party Cruise from Island Party Boat: If you’re looking for a booze cruise with a Tiki theme, book this option. It’s officially billed as a ‘tiki chic’ experience, and even comes with the option to head to the exclusive Admiral’s Lounge where top shelf drinks are served. In short, it’s a slightly more adult version of the traditional booze cruise.
- Ghost & Dark History Night Cruise from First Lady: If you like night cruises, ghosts, and cash bars, look no further. This night cruise lets you see the Chicago skyline when it’s all lit up. As you cruise, you’ll hear stories about the city’s most infamous criminals, disasters, and spooky tales.
Lake Michigan tours in Chicago
- Private Sunset Sail on Lake Michigan from Come Sailing Inc: This private tour takes you across Lake Michigan as twilight sets in. You’ll see the Chicago skyline as its gilded with golden light. This is a private cruise, meaning you can bring up to five guests, put together a playlist, and bring your own drinks and snacks for the duration.
- Lake Michigan Sunset Cruise from Wendella Tours & Cruises: This sunset cruise is similar to the last, except it isn’t private. You’ll share the boat with others and have access to a climate-controlled area, just in case the weather turns cold and windy.
- Small Group Sightseeing Boat Tour on an Inflatable Vessel from Blackhawk Boat Tours: Hop onto a Navy-built Rigid Inflatable Boat for a speed boat-esque adventure on Lake Michigan. Because of the vessel’s small size, all tours are small-group, maxing out at six people.
- Lake Michigan 30-Minute Speedboat Ride from City Cruises: Take on the Windy City at top speeds with this quick boat ride. It’s perfect for anyone who wants a short trip on the water, a quick view of the skyline, and a bit of a thrill. This speedboat can hit 2,000-horsepower speeds.
- Lake Michigan Skyline Cruise from Shoreline Sightseeing: This laidback ride gives you plenty of time to enjoy Chicago’s architectural landmarks before heading out onto Lake Michigan. It’s a relaxing ride for the whole family—and you can even bring Fido with you, as this is a dog-friendly tour.
- Chicago Fireworks Show from Tall Ship Windy: Time your Lake Michigan cruise to coincide with a big fireworks show. You’ll get to experience a nighttime sailboat ride, along with some of the best fireworks views in the city.
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