chicago has beaches small but vibrant downtown north oak main

chicago bikable paths near north side neighborhood where to live

famous touristy fountain in the plaza chicago view of downtown in the background park

the oak club in chicago, illinois cemet architecture

view of chicago skyline home of skyscrapers from pier in front of a beach

washington square park chicago evening blue skies water fountain

chicago parks in summer with view of the tall buildings

at the best rate gauranteed baseball stadium in chicago not wrigley field

best coffee shop cafe in chicago layla and ringos

lincoln park stroll pathways green grass tree cover shade

canal in chicago next to the famous tall residential buidling with great ocean views

outdoor calesthenics park chicago bars workout

pier walk in chicago afternoon covered by trees summer next to beach

STANS donuts and coffee downtown chicago illinois

Chicago (Near North Side) ‘The Windy City’

(Mid-2025, 1 WEEK)

After one week in Chicago, it's my favorite USA city (from May to September).

Air Quality: 45 AQI (can't complain)

Tap Water: 143ppm (Just ok; on par with LA and 120 higher than Medellin)

Dew Point: 71F/22C (humid; dew point is a better measure for humidity)

Chicago is called the “birthplace of the skyscraper” because it was the first city in the world to build a tall steel-framed building that we now recognize as a skyscraper.
Historic Route 66 starts here
LOTs of nice cars (Bentley, Porsche SUV, Top-line Mercedes and BMWs) in my neighborhood
The murder rate is 2x as high as Medellin, but given most happen in the 5-months of good weather (May-Sep), you are 5x more likely to get murderedd in Chicago
An epic big city (2.7 million) with convenience, walkability, good weather (for 5 months), easy beach access, large parks, pretty women walking around
Chicago's population has been declining ever since its peak (3.6 million) in the 1950s

Chicago is a giant city, but the best areas are going to be walkable to the shoreline giving you beach and park access.

Known For: deep dish pizza, Chicago blues and jazz, Second City comedy club, Chicago Cubs, Michael Jordan, Al Capone

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Danny Rusteen

In 2015, Danny got fired from Airbnb. Just two years later, he started two successful businesses and wrote a best-selling book. Since then, he's become a bodybuilding, location-independent, minimalist traveling the world while living in Airbnbs. He describes himself as a skeptic, contrarian, and expert cuddler. In his spare time he reads, cooks, and plays basketball. Follow his journey on Instagram or YouTube.

I choose the items below as they’re generally available everywhere. Thus, easy for comparison. The prices reflect the cheapest option given my standard. In any estination you can find slightly cheaper prices if you wanted to sacrifice convenience (ie going to local market or out-of-town grocery store).