Waterfront dining and a day of boating go hand in hand in Chicago!

POSTED: Jul 21, 2025

Weather you are new to boating, or get out on the water on a regular basis, there are always new delights to discover around Chicago – accessible by boat!

 

O'Brien's Riverwalk Cafe

    O’Briens Riverwalk Cafe on the Chicago River with Tribune Tower in the background. [photo credit: O’Briens Restaurant]

Of course, well-known gathering spots like Montrose Harbor and Beach are a great way to feel like you’re on vacation – with live music acts and festivals throughout the summer – and the patio at Bridge House Tavern for a bite and a drink is an amazing way to end a day on the lake.  But if you are looking for more options, we have gathered together a few more resources to help you plan your next nautical outing!

Smith and Wollensky

     Smith & Wollensky’s [photo credit: thrillist.com)

Chicago River

 

After perusing these lists, you are probably getting hungry for a day on the water filled with food and fun!  Let us know your favorite dockside haunts in the comments!


Images and Sources:  zagat.com, timeout.comthrillist.com, and thinkstockphotos.com

Do you have any other questions about boating without owning or the Carefree Boat Club location?

Let us know via our contact form or on Facebook or Twitter.

#CarefreeBoatClub

Carefree logo_FB