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Water Tower Place, courtesy of Flickr: gabe popa
Water Tower Place, courtesy of Flickr: gabe popa
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5 Struggles Every Chicago Resident Faces

Picture of Elizabeth Newhart
Updated: 9 February 2017
If you’re thinking of moving to Chicago, keep in mind that every city comes with its struggles. Once you’ve researched the best places to keep your Chicago love affair alive, read up on the trials and tribulations that face residents of the Windy City.


Plain and simple. December through March just isn’t pretty in Chicago. Temperatures drop below freezing, the frigid wind whips around the skyscrapers, several feet of snow blanket the city, ice slicks the roads, and the lake-effect weather is generally unbearable. And don’t even think about buying expensive or delicate outerwear, because it will be stained and ruined by street salt in a matter of weeks. Figure out your plan now for surviving the winter before it drives you into a four-month hibernation.


Chicago has a reputation for always being over budget and under-served. The budget crises Illinois often faces result in some city necessities being put off. That means potholes. The City of Chicago website even has a pothole tracker that marks each reported road rubble on a map, and it shows a pretty clear trend. While they exist all over the city, the most have formed on Western Avenue from Diversey Parkway to Cermak Road. So those traveling on Chicago’s west side definitely get the brunt of the biggest holes.

Western Avenue Metra station, courtesy of WikiCommons
Western Avenue Metra station | © WikiCommons

Defending Home Turf

The Second City isn’t just the name of Chicago’s (world famous) comedy troupe. It’s also a label the city just can’t seem to shake when it comes to national reputation next to New York City. Los Angeles surpassed Chicago long ago in terms of population and size, and still the Windy City has to defend itself against its east and west coast counterparts. But residents know that Chicago is one of the most phenomenal places to live, grow and raise a family – not just in the Midwest, but the world. The beaches are beautiful, the museums world-class and the dining unparalleled. And Chicagoans have no issue reminding their New York friends of that.

Sales Tax

Chicago taxes have always been a headache, but the recent increases now have sales tax at 10.25% across the city. It’s now the highest sales tax in the country and was raised one percentage point from 2015, the biggest increase since 2008. It affects a multitude of goods and services across the city, but people have most notably seen the impact on soft drinks, liquor and cigarettes. It’s rough on Chicagoans, who love their caffeine and booze. Greater Cook county also suffers, but Chicago has it the worst.

Water Tower Place, courtesy of Flickr: gabe popa
Water Tower Place | © gabe popa/Flickr

gabe popa


Not every ‘Chicagoan’ has lived in the city forever. But those who live here now can spot a tourist from a mile away, and know the best ways to avoid them. Staying away from obvious traps like Navy Pier, the Bean and the Willis Tower are a given, but it’s not always possible to remain in a complete bubble. Visitors crowd up the city during summer festivals, winter markets and every parade imaginable, but Chicagoans could have a worse problem than people wanting to visit their amazing, world-class city, and everyone typically gets along without too much trouble.

Navy Pier, courtesy of WikiCommons
Navy Pier | © WikiCommons