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17 Best and Worst Things About Living in Chicago

Chicago has a great reputation for its deep-dish pizza and a terrible reputation for its crime. Residents reveal the best and worst parts of living in Chicago.

1: More Moolah for You

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According to a Chicago resident who’s lived in four other major metropolitan cities in the U.S., they claim that Chicago is the “best value for your dollar.” They explain that the city “has tons of great amenities at cheaper cost than other major American metros.”

2: Bad Weather

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Cold, harsh winters are the worst part of living in Chicago for many residents. One local goes so far as to say the Windy City has “Terrible weather 8 months out of the year.” Another said, “The worst thing is, obviously, the weather. The best thing is everything else.”

3: An Architectural Gem

River in Chicago.
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There’s a reason the architecture boat tours are so popular among tourists. A proud Chicago resident says Chicago has the “best architecture of any American city.” They even go so far as to say it has “arguably the best skyline of any global city.”

4: Flat as the Eye Can See

Chicago skyline.
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Chicago isn’t an ideal base for hikers, a negative for some. It’s “very flat,” says one local, with “No Catskills or Mt. Hood equivalent within 5 hours.”

5: Chicago Deep Dish Pizza

Deep dish pizza.
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No explanation is needed about why deep-dish pizza is the best thing about living in Chicago, according to many locals.

6: Numb to Crime

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Chicago has one of the highest homicide rates in the nation, though how dangerous the city is depends on where you live and work. Nevertheless, because there are some extremely dangerous districts in Chicago, a resident says that one of the worst parts about living in the city is “becoming numb to crime.”

7: Great Transportation

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The CTA (Chicago Transit Authority) is one of the best things about the city, according to many locals. It’s fast and easy to get around downtown without needing a car.

8: Where the Wild Don’t Roam

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The worst thing about Chicago for some is the lack of access to nature. One resident says, “You have to get creative about it.” They explain, “I like to canoe in the Fox River or hike through Starved Rock. But pretty much anything requires you [to] make a day or even a weekend of it.”

9: Lots to Do

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It’s hard to be bored in Chicago. A local says there are many food, shopping, entertainment, and lifestyle options. To make it all better? You might not even need to use the CTA; “Pretty much everything is [with]in walking distance,” they say.

10: A Best and Worst Combined

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Chicago is a cultural mecca, something that many are proud of. But while a Chicago resident says diverse culture is the best thing about living in Chicago, they say the worst thing is “people who moved in with Urban Outfitters culture.”

11: Uncle Sam

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Although many believe that a positive thing about Chicago is its affordable cost of living for what the city offers, many say the downside is high taxes and corruption. One local frustratingly points out that they’d be okay paying such high taxes “if it meant good schools, maintained roads, and a decent police force.”

12: A Foodie Haven

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Deep-dish pizza aside, Chicago brims with delicious food options. A resident even dares to say that “Chicago has the best food selection out of anywhere else I’ve lived.” A good BBQ is the only thing missing, in their opinion.

13: Rudeness Abounds

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Let’s start with the good news: “Chicagoans are more polite than most big city people,” says one resident. The bad news? “They are still rude as h*ll.”

14: Great Airport

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Never mind weather delays; a Chicago local says one of the best parts about their city is “having a large international airport that doesn’t have an airline monopoly.” Having two airports equates to lower prices, they say. “Prices in Chicago are 20-50% lower than I paid in Dallas.”

15: Horrendous Traffic

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Those who choose to drive instead of take the CTA are in for a rude awakening. “It is literally a 2-3 hour car ride to get to downtown if you live 40-45 minutes away in normal conditions,” says one resident. “LA and Houston are the only cities I would argue that might have worse traffic.”

16: Job Opportunities

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Several Chicago residents mentioned a strong job market as one of their favorite parts of living in the city.

17: Local Government

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One Chicago resident comes down hard on the local government for making Chicago such a bad place to live. They describe it as “a corrupt, self-serving farce, an embarrassment to the country, and an enemy of the middle class.”

By the Numbers

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More people are moving out of Chicago than into it, according to data gathered by ABC News. Over a 5-year period, the Chicago metro area had a net loss of 294,000 residents.

Source: Reddit.

Rudeness Ranked

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Many locals admit to Chicagoans being rude. Find out where Illinois ranks on the scale of least to most rude states in the U.S.

America’s Rudest States Ranked From 1 to 50: Where Does Your State Fall? 

25 Most Expensive American Cities

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Living in America isn’t cheap, but the cost of living in some cities is downright outrageous. The results are about as blue as each state’s political makeup.

25 Most Expensive Cities in America Breaking Bank Accounts

Best Cities to Retire in the US

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Your Golden Years should be your best years. But according to research by U.S. News & World Report, that may not be the case depending on where you choose to retire. Discover if Chicago makes the cut.

50 Best Cities to Retire in America That Won’t Destroy Your Mood and 401(k)

Southwest Gave Me a $300 Chicago Vacation. Here’s How It Happened

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The stars and pilots aligned during my flight from Malaysia to New York. I couldn’t believe it when I got a free Southwest trip to Chicago.

How I Received a Free $300 Vacation With Southwest

Are You a Top 10% Earner in Your State?

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Whether earning income in the top 10% of your state feels like a pipe dream or a plausible reality, one thing is certain: What constitutes a 10% earner varies wildly by state.

How Much Money It Takes To Be in the Top 10% By State

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