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Since its early days Chicago knew no other way but to develop, endure, rebuild, innovate, and flourish. Significant turning points marked the city’s history. Just when the small 19th century trading post was beginning to turn into a bustling urban hub, the Great Fire of 1871 returned the city to bare simplicity. Most of its historic residential and commercial structures were devastated.

However, this massive destruction was the trigger Chicago needed in order to reinvent itself, kicking off the biggest building boom in the history of the U.S. After all, this is where the modern skyscraper was born!

Originality and innovation tend to trump antiquity when it comes to Chicago’s houses as well. After the fire, the wood structures were replaced with modern steel and stone buildings. Architects like Frank Lloyd Wright developed an organic and distinctive architectural movement, the famous Prairie School. Bungalow and Modern style homes designed by Ludwig Mies van der Rohe’s and other brilliant architects – the Second Chicago School – were also born here.

Today, the Windy City is filled with architectural evidence of a storied and inspiring past. Take a visual tour of 165 years of home architecture in Chicago and discover beautiful homes created in a great variety of architectural styles. Images courtesy of Google Maps Street View, with data provided by PropertyShark:

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Local Landmarks

Following the European architectural trends, Victorian, Queen Anne, Greek Revival, and Colonial home styles were in high demand before the Great Fire.

An 1854 landmark displaying a lovely Victorian style is the Wingert House, located in Norwood Park West. This is one of the oldest farmhouses that still stand in Chicago today, built in the middle of the 19th century by a German immigrant fleeing religious persecution.

The Prairie School architecture that became popular in the 20th century influenced many architects and designs. At the turn of the new century, F.L. Wright built the William and Jesse M. Adams House in Beverly. Today a Chicago landmark, the residence was last sold in 2014 for nearly a million.

Chicago’s Bungalow Belt

The first half of the 20th century also saw the rise of the popular Bungalow architectural style. More than 80,000 small to mid-sized Chicago houses are built in this style and still stand today across various “Bungalow Belt” neighborhoods.

Bungalows share some specific characteristics such as low-pitched roofs (gabled or hipped), 1 or 1 ½ stories, covered front porches with columns, and dormers. Still, most strive to be distinctive, either by color, size, shape, or other stylistic features.

Located in the historic bungalow district of Rogers Park Manor, this 1920s bungalow at 2434 West Farwell Avenue features Arts and Crafts influences, such as a unique battered stone post. It was designed by Lyman Allison, an architect responsible for 26 other bungalows in the area.

Corner lots were ideal for larger, more elaborate bungalows. Built later, in 1928, this single-family home at 7758 South Crandon Avenue in South Shore showcases a deeply recessed corner entrance, a polygonal front bay, and terra cotta tiled roof.

Buying a house in Chicago

If you want to own a piece of Chicago architectural history, you might have to pay a considerable amount, especially if the property was carefully restored in order to preserve its antique flare.

This 1869-built fully renovated brownstone in East Lakeview is a 3-level, 6-bedroom jewel boasting 6,800 square feet of living space, a backyard urban oasis, plus an extra coach house which rents for about $40,000/year. All these can be yours for $2,595,000.

But Chicago is not all million-dollar mansions. Consider this tastefully decorated home with Tudor-style influences built in 1927 in Beverly. It’s going for $369,900 and it features 3 bedrooms, an outdoor garage, a wood burning fireplace, and many recent improvements. Lovely, isn’t it?

Renting a house in Chicago

Of course, you can always rent a wonderful Chicago home, until you can afford a F.L. Wright gem!

This three-bedroom rental house located in North Side Chicago is awaiting new residents for $2,275/month. Offering 1,642 square feet of living space, the pet-friendly crib is perfect for any family. It features a fireplace, a welcoming back yard, and plenty of storage space. The brick facade adds a nice vintage touch.

Historic or modern, expensive or affordable, bought or rented – Chicago homes never cease to impress and appeal to all tastes. Which one’s your favorite?

* [July, 31] This article has been updated to include the ‘Chicago’s Bungalow Belt’ section

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