Just when you thought the harebrained plans of the Democrats running our beleaguered big cities couldn’t get any more wacky, Chicago has adopted another doozy. The Windy City is increasing hotel taxes to increase tourism.
Ordinance 2026-0022544 will increase the tax on hotel rooms in that district from 17.5% to 19%, with proceeds going to an organization called Choose Chicago, which will use the money for tourism marketing campaigns.
The top goal on Choose Chicago’s bucket list of events is the 2028 Democratic National Convention, and now anyone who books a room at Second City can contribute to this effort.
Chicago Mayor Brandon Johnson listens as Illinois Governor JB Pritzker speaks at a news conference to explain President Donald Trump’s plan to send National Guard troops to the city on August 25, 2025 in Chicago, Illinois. (Scott Olson/Getty Images)
It’s quite something: Only a left-wing Democrat could think that making a visit to Chicago more expensive will increase tourism. Maybe they should introduce a free heist to sweeten the deal.
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Now ordinary tourists and working-class business travelers will pay directly out of their own pockets for a Democratic campaign to lure the Democratic Party to the city.
What we’re really seeing at play here isn’t so much an attempt to lure travelers to Chicago, but rather some kind of Tammany Hall-style patronage program, with the Democrats running the city handing out expensive jobs to their friends.
This, on a slightly smaller scale, is exactly the kind of scandal that sank Kristi Noem’s tenure as Secretary of Homeland Security, after she allegedly gave advertising contracts worth hundreds of millions to those closest to her and her lover, Corey Lewandowski.
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Let’s be honest: who are the Democrats running Chicago that they are likely to hire to attract the DNC? Probably the exact same people who make their political ads.
Tellingly, this costly effort to sell Chicago as a travel destination is not aimed at the average family taking a trip to one of our nation’s major cities, but rather at convention attendees who are racking up more hotel points.

The “Greetings from Chicago” mural illuminates a street in Chicago’s Logan Square neighborhood on March 30, 2018. (Patrick Gorski/NurPhoto via Getty Images)
It’s the far-left Democratic Party in a nutshell: working-class families paying the bills for liberal elites.
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It’s not just higher hotel taxes that keep the average Joe from packing the minivan and heading to Chicago with his wife and kids. It’s that our urban centers are fast becoming playgrounds for the wealthy rather than family-friendly environments.
In big blue cities like Chicago, Portland, San Francisco and Philadelphia, you expect to walk over half-dead vagrants with needles in their arms, something no parent likes to explain to a young child.
But for the conference class it’s no problem at all, they just get in their Uber X on the way to the steakhouse and fly past the wrong kind.
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Chicago is sending the same message to the American working class as Democrats are sending across the country, that travel and tourism are not for you, that you should stay home, watch Netflix and order UberEats while the rich people indulge.
For once, can Democrats pass a city law that makes things cheaper for the middle class?
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The left’s concept of governance seems to be to make everything essentially free for the poor and immigrants, to keep the rich under a bit of control, and to burden the ever-shrinking middle class with the bill.
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But don’t worry, the advisor class will do very well in this deal as Choose Chicago provides them with taxpayer-funded perks to use their conferences who also pay the taxes that go directly back into giving perks.
Nice job if you can get it.
The family road trip is a staple of Central America, and Chicago, with its museums and fantastic architecture, should be the jewel of such trips. But the city’s government doesn’t seem interested in that. After all, those families have no political connections.
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If Chicago scores the DNC, I’ll probably be there, my company paying the new hotel taxes while I strut around in expensive suits and drink expensive martinis. But if I want to take my son with me for a week, it will only become more expensive.
It’s the same old story with the Democrats, who are always taking money from hardworking Americans to give to their friends, and now anyone who visits Chicago can contribute.
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