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Photo: Thshriver, CC BY-SA 3.0 via Wikimedia Commons
Near Old Town, on what's often referred to as the Gold Coast, Astor Street was named for the fur tycoon John Jacob Astor, and does him tribute on his favored terms — these are the most expensive houses in Chicago. The atmosphere is the main attraction, but the 1892 Charnley House (1365 N Astor St) is particularly interesting, marking a halfway point between the distinctive styles of master architect Louis Sullivan and his apprentice Frank Lloyd Wright. There are also some interesting Art Deco homes like Holabird & Root's design at 1444 N Astor St.
The Astor Street District is a historic district in Central Chicago, Illinois.
© OpenStreetMap contributors
Housed in a historic mansion, the museum contains four floors of exhibits dedicated to the history of medicine and surgery and is filled with artwork and artifacts ranging from Incan surgical tools circa 2000 BCE to state-of-the-art prosthetic joints. Of special interest to those in the medical field, the collection appeals to anyone interested in history, art, science and architecture.
Chicago Historical Society
A creative urban history museum. Exhibits include The Pioneer, the first railroad locomotive to operate in Chicago, and the bed upon which Abraham Lincoln died; more fun for kids is the Chicago-style Hot Dog showcase, which supplies all the giant plastic ingredients you'll need to turn yourself (or your little brother) into a life-sized hot dog (no ketchup, of course). They also host regular tours of different CTA lines and walking tours of Lincoln Park and Old Town.
Quite possibly the beach volleyball capital of the Midwest. There are semi-pro leagues here, and plenty of nets for amateurs to show up and play. There's also an enclosed roller-hockey rink and plenty of people whizzing past on the wide bike lanes. The North Avenue Beach House is a big boat-shaped structure at the center (look for the red smokestacks) where there are a few food and drink options, occasional live music, and Park District offices. A couple blocks south, toward Oak Street Beach, there are chess tables.
A member of the River North gallery scene, with contemporary art, including paint, drawings and sculpture.
Several blocks of beautiful cottages and row houses, notably the five at 1826-34 N Lincoln Park West, which were designed by Louis Sullivan in 1885. The anchor of the district is St. Mike's (below).
Unveiled in 1869, the walls of St Mike's were all that remained after the Chicago Fire swept through Old Town, making it one of only six structures to survive — and the tallest in the city until 1885. A tower was added in 1887, and the current stained glass windows date from 1902. A Catholic church run by the Redemptorist congregation, it has seating for more than 1000 people.