The Chess Pavilion is a hidden gem in Old Town. Located near North Avenue beach, this concrete pavilion overlooks Lake Michigan and a jaw-dropping view of the skyline. Come bring a chessboard, and sit with a leg on each side of these great cement blocks, with a black and whiteboard in-between. You’ll likely encounter some chess pros who will invite themselves to the bleachers of your game.
Oz Park brings the magic of The Wizard of Oz to Chicago. Complete with a Yellowbrick road, statues of the characters, and an “Emerald Garden”, this delightful park is a great place to pack a lunch, enjoy a Chicago summer, and reminisce on some childhood memories.
Located in Chicago’s Northside Edgewater neighborhood, this beach stands out for its cleanliness. Away from the tourists, you feel like you’ve left the city for a bit and you’re on the coast. Filled with great views and beach shacks for snacks, Hollywood Beach is a great weekend “get away” from the hustle and bustle of the concrete jungle.
Also known as Osterman Beach
This 2.7-mile elevated trail once was the Bloomingdale train lane and has since been converted to a haven for runners, walkers, bicyclists, and art admirers alike. Stroll this east-west trail on Chicago’s northwest side while enjoying art installations, local views of the city, and truly getting to “be with the locals”.
Chicago is home to some of the best brews around. Many breweries offer free tours that come with a tasting at the end. My personal favorite is Lagunitas. Walkthrough their trippy Charlie and The Chocolate Factory-esque entrance, and see beers swinging past you on conveyor belts. It’s truly a grown-up candy factory.
The Bridge and River tour is a scenic 3-hour bicycle tour will take you from the Upper West Side of New York City up and over the George Washington Bridge for a ride along the river on Route 9W. Get the full touring experience and leave New York City for a few hours. During the ride, we make stops at Grants Tomb Memorial on the Upper West Side.