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It has always been on Amanda's bucket list to go kayaking; specifically on the Chicago River. For a Chicago native this is a must try activity! No outdoorsy adventure sport prerequisites required. Any and every one will enjoy the beautiful architectural and scenic views the river has to offer. For some odd reason it took Amanda 35 years to try it, but finally getting in that kayak with her toddler was worth the wait! Never would she have imagined taking her (extremely active) toddler along for the ride yet it made it an even more memorable experience.


If you've ever walked along the Chicago River you know it's common to see tons of kayakers. One of the most popular activities is guided kayak tours, but it's not uncommon to see individuals or small groups gliding along the water too. There are several options when it comes to choosing the perfect river outing. If you're looking for flexibility in time and dates there's always the opportunity to rent individual and double kayaks with no tour guide. There's countless launching areas at any point along the river. If you want to learn more, meet people, and/or are more comfortable navigating the waters in multiples there are opportunities for guided group tours. So how do you choose the perfect kayaking experience? We'd consider the following:


  1. Single or Double Kayak: Single kayaks are definitely more of a physical challenge. One person doing all the work vs two. As you can imagine double kayaks are larger and more challenging to flip over even though it is unlikely you will on either. Sonny comfortably sat in-between Amanda and her husband in a two person kayak. Before entering the water we got a comprehensive explanation on safety and rules from instructors which was comforting.

  2. Scenery: What do you want to see along the way? Is your goal to see the world renowned Chicago architecture, restaurants and sights along the Riverwalk? Are you planning to see the Navy Pier fireworks? Or is your goal to enjoy a more peaceful adventure filled with more nature and less hustle and bustle? Kayaking along the Riverwalk gives you a front row seat to some of the prettiest architecture, but that comes with a compromise. You do have to navigate with more caution since this is a high traffic path for other kayak, boats (small, large, and extra large), the water taxi, sightseeing tours and more. The seasonal foliage has to be stunning in the upcoming fall months along the river so taking the path less traveled may be beneficial. Another cool place to check out is Metropolitan Brewing at 3057 N Rockwell St. They are located on the river near a launching sight and you can grab a drink before or after you kayak.

  3. Time & Money: We recommend kayaking on a weekday during off peak hours to avoid as much boat congestion as possible. The river on the weekend is filled with boat rentals, yachts and more tours. If you are heading out on a weekend a large tour may be more comforting for a first timer. Going with a group or tour will require more planning, but I'm sure you can find some great discounts! We were charged by the hour and went by ourselves during the week. It was very peaceful even though we took the most popular route to see the architecture. Groupon and various social media sights run discounted rates. East Bank Club members also receive a discount at Water Riders. We did not have to pay for Sonny (2 years old) and just had to pay for ourselves.

Those are the top three things we would consider before heading out on the water! The top rated places we found online include:

  • Kayak Chicago

  • Wateriders (two locations - one by Metropolitan Brewing and one in River North by the Riverwalk)

  • Urban Kayaks

  • Chicago River Canoe & Kayak

If Kayaking isn't your thing we highly recommend seeing the river by boat whether that be a private boat rental, the water taxi or an architectural tour! Even a life long Chicago native will be impressed by the scenery and skyline! Our experience kayaking with our kids was one we will never forget. Sonny was mesmerized by being on the water and if he managed to sit still the entire time any kid will! At first Amanda was nervous, but all those fears dissipated once we started our journey. We didn't go as long or as far as we probably would have if Sonny wasn't with us. We wanted to make sure he didn't get antsy since there isn't anywhere to stop but where you launched from. We were on the water for more than an hour and he didn't move a muscle or make a peep (a rarity). We're looking forward to our next water adventure with and without our kids!


X0 - Amanda & Katie

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