Summer In Chicago

Living Your Best #LakeLife – Chicago Style

From beaches to bike paths, life along lake Michigan sparkles.


If you’re from the East or West Coast, you might travel to Chicago thinking it is the city of no coast – but be ready to be pleasantly surprised. Our magnificent lakefront feels like the ocean in scope, is steps from Downtown in proximity and boasts some of the most unique ways to enjoy water that a visitor or local could ever dream of. 

Let’s start with the lakefront trail. Over 18 miles of public pathway separate the lakefront from the skyscrapers to form a breathtaking view, connecting the North and South sides of the city and winding through the heart of downtown. This masterful stroke of urban planning connects four major lakefront parks and various beaches making them easily – and pleasantly- accessible by foot, bicycle (take one of our Heritage custom bikes!), scooter or stroller. Step out of our lobby and you are only feet from a one-of-a-kind urban adventure.

Or, set sail on the historically accurate, 148-foot traditional four-masted gaff topsail schooner ‘Tall Ship Windy!The architecture, fireworks or even the pirate cruise boasts a ride with majestic sails and noble profile ready to launch you into lake Michigan for a grand adventure – and a grand view. She sets sail from Navy Pier – just under two miles away from us.

Or hop over to Dusable Harbor (less than a mile walk straight through Millennium Park) and jump on a living piece of history aboard the Fred A. Busse – a beautiful red vintage fire boat that saw real action until her retirement in 1981. Take the Busse on an architecture cruise out on the lakefront and then in through Chicago’s complicated and fascinating set of locks that lead you into the Chicago River. This floating museum also offers a 21+ Brew Cruise in partnership with a local brewery, sunset cruise and firework cruise – all of which remain on the lake and boast spectacular views and another beautiful walk home through Millennium Park. 

Pop out of our landmark lobby and head south for a little nature at Northerly Island! The intersection of Chicago’s natural and built environments, this man-made island stretches between Grant and Jackson Parks and features prairie grasslands, a 5-acre pond and wandering strolling paths. You might not want to leave – if so, throw your walking shoes in your backpack because, well look at that, you’re also at the home of the Huntington Bank Pavilion. Summer 2022’s got a lot going at this gorgeous outdoor music venue – depending on the timing of your visit, you could catch My Morning Jacket, Phoebe Bridgers or Alicia Keys under the summer sky.  

Final lakefront tip: Let the sunbather’s have noonday – savvy adventurers head out to one of Chicago’s lakefront beaches for a sunset picnic (there’s plenty to pack on the salads and sandwiches front from Fairgrounds’ eclectic menu!) on a Wednesday or a Saturday evening. Simply plunk down your blanket, spread out your picnic and get ready for the ultimate view of fireworks over the lake. Launching from Navy Pier every Wednesday and Sunday at dusk, you’ll get double the dazzle as the fireworks light up the night sky and reflect off Lake Michigan. If you can pull your gaze away to look towards the city, you’ll also see the skyscraper windows a glow – an only-in-Chicago memory-making experience not to be missed. 

Don’t have time for a full #lakelife adventure? You can’t go wrong by heading up to Cindy’s where you can rest assured you will AT LEAST have the best view of the lake to enjoy. 

Any of our special offers are ready and waiting for your next water adventure!