Kayak Chicago River | Finding The Best Ways To Kayak Chicago River

To kayak Chicago River is one of the most enjoyable activities to do while visiting Chicago. In the event you live in Chicago, or are new to the area and plan to stay for a while, going kayaking provides a fantastic opportunity to meet new people and serves as a great first date opportunity.

However, it’s important to know the best way to kayak Chicago River in order to get the most out of the experience. Without a game plan going in, you risk getting lost or simply not seeing and experiencing the absolute best the Chicago River has to offer.

With that said, knowing the best way to go about kayaking Chicago River allows you to experience the very best the city has to offer and can leave you breathless at just how amazing of an experience it actually is.

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For your benefit, we have laid out the way to kayak Chicago River, including information about the Chicago River, various kayaking tours you can go on in downtown Chicago, and places to go when you want to kayak outside of the downtown portion of the city. Therefore, regardless of whether you love kayaking in the city at night or taking a day trip to the less urban areas of Chicago, the Chicago River has something for you.

About the Chicago River

The Chicago River runs through the heart of downtown Chicago and is largely responsible for Chicago becoming such a large city in the United States. The Chicago River – which takes water from Lake Michigan – is 156 miles long and has a working system of canals as well.

There are three main sections to the Chicago River: the main stem, north branch and south branch. The main branch which includes the Chicago Riverwalk runs through the heart of the city. Although the north and south branches are still largely considered within urban dimensions, they are typically less populated than the main stem.

Along with kayaking Chicago River, there are numerous other fun activities and events you can take part in, including fishing, cruises, sightseeing and walking along the docks in the downtown area. Also, due to the close proximity to the city, there are a large number of delicious restaurants and places to shop after your time at the river is finished.

Another interesting characteristic about the Chicago River – which isn’t the case with many other large rivers within large cities – is that it is encouraged by the city to use the river whenever it’s desired. City officials believe by encouraging tourists and citizens of Chicago to use the river for recreational use, it will increase public motivation to keep the river from becoming polluted, which is the case with many other big city rivers. The city also is famous for dyeing the river different colors as means of celebration, such as dyeing it green for St. Patrick’s Day or blue when the Cubs won the World Series.

kayakingBest Ways to Kayak Chicago River

kayak chicago river

There are numerous ways to kayak Chicago River, and the method you choose should be largely dependent upon your personal preference. If you prefer to kayak at night as opposed to the daytime, then check out the tours that occur at night. If you prefer daytime, then perhaps a trip to the outskirts of the city where it’s less populated is a better option. Also, if you want to bring your dog to the river, then you can do that in certain areas as well.

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The following are ten different ways to kayak Chicago River. While you can simply go for a leisurely stroll on the main stem, a tour is an even better way to enjoy your time out kayaking Chicago River. Escaping the city and engaging in more adventure can be rewarding as well.


There are numerous tours to embark upon on the Chicago River, and you are likely to find a tour that you love, no matter how crazy you think it is. From a simple history tour during the day to a night kayaking tour that involves scary stories, the Chicago River offers it all. The following are five of the best tours the Chicago River has to offer.

Historic Chicago Tour

Going on the Historic Chicago Tour offered by Urban Kayaks is a great way to experience the Chicago River during the daytime hours. The city of Chicago is rich in history, and it was quite literally built around the river itself.

The Historic Chicago Tour allows you to learn more about the rich history of Chicago while getting outside and having fun interacting with others. Before the tour begins, there is a 20 minute tour session where the tour guide discusses safety measures and what all is on the agenda. After getting into the river, you are shown around the city of Chicago by the tour guide, who occasionally tells stories of Chicago’s deep and intriguing history.

The tour takes approximately 90 minutes once you are in the water. It’s encouraged to arrive 20 minutes early in order to check in and get settled.

Be sure to dress according to weather and plan in advance for the possibility of getting wet. One of the best parts about the Historic Chicago Tour is that they provide kayaks for you to use, so you don’t have to worry about carrying your kayak around the city of Chicago.

For anyone who loves going kayaking and has an interest in learning more about the history of Chicago – which has one of the most intriguing pasts of any city in the United States – the Historic Chicago Tour is the perfect way to kayak Chicago River.

The tour guides are friendly, the trail is easy, and the history is simply fascinating. The Historic Chicago Tour has an outstanding reputation for providing an entertaining evening, and understandably so.

Sunset on the Riverkayaking chicago river

There are various different places that offer a sunset tour on the Chicago River, including Urban Kayaks and Kayak Chicago. They are both reasonably priced, and the one that is best for you is completely dependent upon your personal preference, which may factor in time on the water, exact location, etc.

A Sunset on the River Tour is exactly what it sounds like, but it may even be more exciting than you think. Watching the sunset over the water is a breathtaking experience, especially when surrounded by the beautiful view of Chicago’s city lights. Going on a Sunset on the River Tour is also a great opportunity for the entire family to spend an evening together, not just the adults. Also, there tends to be far fewer kayakers and boats on the water in the evening, which makes it the perfect event for those who are new to kayaking.

Depending on which tour you choose, the tours typically last between 90 minutes and an hour and a half, with a 15-20 minute pre-tour involved to go over safety measures and the agenda for the evening. You don’t need a lot for Sunset on the River, but you will need to prepare for the possibility of getting wet and most importantly, don’t forget the camera!

In the event you choose the Sunset Tour by Urban Kayaks, you will launch from their beautiful Riverwalk location. Both Urban Kayaks and Kayak Chicago provide various forms of kayaks to choose from, including single, tandem, and paddleboards.

For anyone looking for a low effort, leisurely kayaking experience that provides a magnificent view of nature, going on a sunset tour is the perfect option.

Night Paddle

Going on a night paddle is another great way to experience the beautiful lights of the city while avoiding the hectic traffic caused by boats and other motorized watercrafts during the day.

There are several different places that offer a night paddle on the Chicago River. Arguably the three best are the City Lights Night Paddle, Moonlight Paddle and the Navy Pier Fireworks Paddle, which includes a large fireworks show as a part of the kayaking tour. Depending on your preference, you may find one to be more appropriate than the other, although all three of these options provide a fantastic, fun night out kayaking Chicago River.

The average trip during a night paddle includes a quick orientation to go over safety measures and the agenda for the night, followed by a slow stroll down the river, taking in the breathtaking view of the city lights and magnificent glow of the water in the Chicago River. For the Navy Pier Fireworks Paddle, you get to experience a lovely fireworks show in the middle of the tour, which makes it the ultimate date opportunity.

While it’s important to keep track of where they are at all times, going for a night paddle is extremely safe for children, especially within the confines of the tour. Subsequently, a night paddle tour is a great way to get the entire family to bond together.

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Similar to most tours, you won’t need much for equipment as the tour guide is likely to provide you with everything you need, including kayaks, paddles and life jackets. However, be sure to bring your camera as you just might take a picture of the next phone screensaver.

Ghost and Gangsters Tour

If it sounds pretty creepy, it’s because it is.

The Ghost and Gangsters Tour is a fantastic way to kayak Chicago River at night when it’s quiet and learn information about the rich history of Chicago’s infamous underworld.

The Ghost and Gangsters Tour offered by Water Riders explains how exactly Chicago developed their Wild West reputation and gave birth to some of the most infamous criminals ever, including Al Capone himself. Along the route, you also are taught about various ghost stories and haunting rumors that have formulated around the Chicago River. The scary stories include a tail of how every person in Chicago feared a man the size of a child and a particular part of the area that is considered haunted by many.

For anyone who loves a good ghost story, is fascinated with the rich criminal history associated with Chicago’s past, and loves a relaxing kayaking trip at night, the Ghost and Gangsters Tour is the perfect way to experience all three in one event.

The tour takes around two and a half hours to complete, which includes a 20 minute orientation followed by two hours on the water. There isn’t much you need to bring other than clothes you don’t mind getting wet and a camera as Water Riders provides kayaks, paddles, and life jackets for you. Although the content may be considered too scary, it is safe for children to come along, and there are tandem kayaks available for multiple people to share a single kayak.

The tour guides are always very fun to be around and can tell one heck of a ghost story that is certain to change the way you view Chicago forever.

kayaking the chicago river

Do Something Different

While a traditional, leisurely stroll down the Chicago River with a group is extremely exciting, doing something non-traditional can be a fun way to make the most out of the experience kayaking Chicago River.

The two most interesting ways to mix it up and do something different while kayaking are to embark in either Paddle Board Yoga or Puppy Paddle, which are tours offered by Urban Kayaks.

Paddle Board Yoga is an opportunity for you to get out on the Chicago River in the Monroe Harbor and participate in a fantastic, fun yoga session while kayaking. The tour is always hosted by a certified yoga instructor who is able to tailor the session around the experience of the group, which means no previous yoga experience is required.

There isn’t a more peaceful place to practice yoga than the Chicago River, so if you love yoga and kayaking, be sure to take advantage of this amazing opportunity.

Another great way to do something different on the Chicago River is to participate in Puppy Paddle, which allows you to take your dog with you on the tour. Urban Kayaks offers several different kayak options to choose from and life jackets, although it is recommended that you bring your own puppy life jacket if you have one. There is a high likelihood you are going to get wet when your dog tags along, so be sure to dress appropriately and be prepared for the possibility of leaving completely soaked.

If you like to be active and have fun, or you simply love your dog and want him to experience the Chicago River as well, then one of these two options might be the best way to kayak Chicago River for you personally.

Escape the City

While tours are amazing opportunities to meet others within the city and learn about the rich history of Chicago, sometimes getting outside of downtown and experiencing all the more rural areas the Chicago River has to offer is great for a more peaceful, quiet adventure.

Skokie Lagoons

The Skokie Lagoons – which are controlled by Cook County – are a great place to go when kayaking Chicago River. They are well outside of Chicago and offer a true kayaking experience full of wildlife and faster rapids.

The Skokie Lagoons are manmade lagoons that range around seven miles in length, although there are stopping points all around the route that make it easy to complete a trip that is much shorter.

One of the most appealing parts of the Skokie Lagoons is that they give you the ability to bond with nature. All along the route you are likely to see wildlife, and it is the perfect place to go when trying to get away from the stresses of reality.

Also, there are various other activities you can do within the Forest Preserves of Cook County, including biking, hiking and fishing.

The Skokie Lagoons are typically highly populated, so you might not be able to gain complete seclusion, but it still much less populated than the main stem of the Chicago River. It will feel as if there isn’t a big city within a thousand miles.

The Skokie Lagoons tend to be faster than the main stem of the Chicago River and there is an increased chance of getting wet, so make sure you dress appropriately. You also need your own kayak, life jackets and helmet, as well as any other items you deem necessary.

For anyone in Illinois searching for a great place to kayak outside of the big city, the Skokie Lagoons are a fun, convenient place to visit.

South Branch

Although the South Branch of the Chicago River is still in Chicago, it is on the outskirts and is generally much less populated than the main stem of the Chicago River. The South Branch begins around the Chicago Watercraft located at River City Marina, and ends right around La Villita Park in Chicago.

There are various routes you can take on the South Branch part of the Chicago River. While simply unloading the kayaks at the Chicago Watercraft is a convenient starting point, another great route to try is from Ping Tom Memorial Park to S. Western Avenue, which is a total of four miles in length with multiple rest points along the way.

The South Branch in general is a much harder-to-navigate area, and it is recommended for more experienced kayakers only. With that said, anyone who is up for a challenge while kayaking Chicago River is sure to love this route. Along the route, there are various convenient stops if a break is needed, and there are fantastic restaurants to try out as well.

If the goal is to get away from largely populated areas, then the South Branch may not be the most ideal place as it is typically populated with motorized vehicles that can cause quite a distraction. However, it is a fun, challenging route that provides a great opportunity to soak in the amazing scenery that Chicago provides.

Also, be sure to dress appropriately and wear a helmet and life jacket as you are certain to get wet.

North Branch

The North Branch of the Chicago River is just below the Skokie Lagoons and provides a balance between the calm and quiet that comes with the Skokie Lagoons and the excitement and activities that can be found around the main stem.

The North Branch has some traffic, but it is far less populated than the main stem of the Chicago River. It makes for a fantastic kayaking opportunity. With that said, motorized watercrafts are allowed in the North Shore, so be careful while kayaking in the area. The North Branch is an extremely scenic area that allows for the view of the city while still giving a less urban feel to the trip than the main stem does.

If you want freedom and to kayak Chicago River in an area that is less populated, but still want to experience the social interactions and activities provided by being closer to downtown, then the North Branch is the perfect place to drop in.

Much like the South Branch, the North Branch is also slightly more difficult to navigate than the Skokie Lagoons or the tour areas of the main stem. Be extra careful if you plan to bring the kids along on the trip.

While it is difficult to have success fishing in the main stem, you are able to increase your chances of catching something when fishing in the North Branch. So it is a great place to go fishing while kayaking Chicago River. Other than your kayak and safety gear, there isn’t much that is needed to have a great time out on the water in the North Branch.

North Shore Channel

Another great place to kayak Chicago River when attempting to escape the hectic nature of downtown Chicago is the North Shore Channel. The North Shore Channel is located close to the Skokie Lagoons, and like the Skokie Lagoons, the North Shore Channel is manmade, designed perfectly for a fun kayaking trip.

The North Shore Channel – which is 6.7 miles in length – generally has a slow water stream and is perfect for those who are new to kayaking and children to who need to learn the proper way to kayak without numerous motorized watercrafts flying by.

It’s also a great place to go if you simply enjoy experiencing nature, as it isn’t uncommon to see numerous wildlife as you float down the channel. The North Shore Channel is also an excellent place to go for individuals who love to fish.

There are typically far fewer power boats and less overall traffic in general at the North Shore Channel, which means you can safely bring the entire family down for a day kayaking Chicago River away from the bright lights and numerous distractions that downtown Chicago provides.

Lastly, there are various other activities that you can do along the North Shore Channel outside of kayaking, such as biking and hiking. The North Shore Channel, mainly located in Cook County, is a great place to go when wanting to teach the children about nature in a calm, peaceful environment.

Montrose Beach

Montrose Beach is a beautiful location located on N. Lake Shore Drive in Chicago. The artificial beach – which is Wi-Fi accessible – has a section that allows you to bring your dog and go kayaking.

If you like the idea mentioned above about allowing your dog to experience the fun of going kayaking, but you are skeptical about bringing your dog into a group environment, Chicago River at Montrose Beach is an excellent way to do it on your own time and at your own pace. Dogs love kayaking, and if you love your dog, then it only makes sense to take up the amazing opportunity presented by Montrose Beach.

With that said, Montrose Beach is a fantastic place to kayak Chicago River with or without a dog. While there is a significant section of the beach dedicated as a dog beach, a larger section is for general use and allows you to drop your kayaks in.

Simply drop the kayak in the water, paddle around the area and soak up all of the sights and sounds the city of Chicago has to offer.

While it’s important to remain safe and wear the proper protective gear, especially if your dog is with you, Montrose Beach is a safe place for the whole family to go and kayak Chicago River. However, be sure to bring a camera as there is likely to be memories made that you want to look back on as time passes.