Sunnyside

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A question for you. Have you ever wondered where Ravenswood began? It started with a vision of an exclusive commuter suburb. Back in 1868, some real estate guys formed the Ravenswood Land Company. They bought 194 acres of land north of Chicago. Their plan hinged on a deal with the Chicago and North Western Railroad. The railroad agreed to open a new stop. But there was a catch. The company needed to guarantee a certain number of passengers.

To attract wealthy residents, the company divided the land into large lots. They set a high price of $7.20 for a hundred rides on the train. The Sunnyside Hotel was their ace in the hole. It sat next to the original 194 acres. Potential buyers could experience the area as resort visitors. By 1874, the lone commuter had grown to 75.

The Ravenswood Land Company didn’t build much. Residents recalled muddy streets and open ditches. These existed alongside the nice houses and lawns. Private money paid for some improvements. But Jefferson Township blocked Ravenswood’s sewers. They didn’t want them running through their land into the Chicago River.

Everything changed in 1889. Both Lake View and Jefferson Townships joined Chicago. Suddenly, the big city controlled local improvements. Ravenswood finally got its sewers. Electric streetcar lines arrived in the 1890s. The L train extended in 1907. The area became accessible to more people. Smaller houses and apartments filled the gaps. These stretched between Chicago and its former suburb.

The name Ravenswood stuck around. Even after it became part of the Lincoln Square Community Area, people still called it Ravenswood.

Now let’s talk about the Sunnyside Inn. Legend says Abraham Lincoln visited it. Journalist Jacki Lyden heard the same story. She wrote about it in her book. Sadly, there’s no real proof. But the Sunnyside Inn was real. It was a famous roadhouse. People also called it a cemetery saloon. It inspired other venues like Green Mill Gardens.

The Inter Ocean newspaper wrote about it. It said the inn was the best known of all the roadhouses. It stood at what is now Sunnyside Park. When did the Sunnyside Inn open? That’s a mystery.

The Inter Ocean reported the inn was around. This was back when Chicago was a small village. It was the 1830s or 1840s. Indians were still common. At first, the inn didn’t have a name. The newspaper said a toll-road company owned it first. The Rosehill and Evanston Road Company ran the toll road in 1860.

Samuel Cap Hyman bought the Sunnyside in 1866. He was a gambler. He held a party for Chicago’s demi-monde. The Tribune newspaper reported on a quarrel. Guests exchanged insults and blows.

The Sunnyside became a place for the gay set. It had prize fights and poker games. Horse races were also held there. People didn’t care about rules. Rumors of encounters drifted into Chicago.

In 1867, newspapers wrote about crimes near the Sunnyside. Three pugilists were charged with riot. The Tribune reported a brutal attack on a woman. She was assaulted after being told they were going to Sunnyside.

Cap Hyman didn’t own the Sunnyside for long. In 1869, the hotel was for sale. Meanwhile, land across the street was being sold as lots. The developers called their new village Ravenswood.

The Sunnyside Inn and hotel played a role in the area’s development. It gave its name to Sunnyside Avenue. Today, it’s a reminder of the area’s vibrant past. It’s a past filled with gamblers, travelers, and the seeds of a suburb.

After discovering the story of Sunnyside in Chicago, you may wonder how to explore even more. Explory makes it simple: our digital Chicago guide connects culture, history, and unique experiences. With the interactive Chicago city guide, you can dive deeper into the local atmosphere and follow curated routes that turn your visit into a memorable Chicago city tour. Explory is designed for authentic Chicago exploration. Each Chicago guide highlights iconic places and uncovers Chicago hidden gems that many visitors never find. With the immersive Chicago audio guide, stories and sounds bring every step to life. Our flexible Chicago city guide makes it easy to plan routes, discover landmarks, and enjoy storytelling that connects you with the city. Whether your passion is art, history, or local culture, Explory ensures your Chicago city tour is unique. With a strong focus on Chicago exploration and surprising Chicago hidden gems, Explory gives you more than sightseeing – it creates real discovery. Download the Explory App to expand your journey. Discover more than 300 cities and over 500,000 POIs and stories worldwide. Whether you need a Chicago guide, a reliable Chicago audio guide, or a flexible Chicago city tour, Explory is your key to travel differently.

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