Chicago in Summertime

The Windy City is so called not for the actual wind that runs through its streets (which gets particularly intense at intersections near the Sears Tower), and nor is it called “windy” because of its architecture, as some claim. It’s called windy because of its intense politics—but that’s not the only way that Chicago expresses itself in heat. The summer months in Chicago last from the end of May through August, and the city lets you know that it’s summer in more ways than one.


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Talk of rough seasons is a point of pride for Chicagoans. They might complain sometimes about the heat, or about the cold, but they’re glad to live somewhere where the seasons are distinct and each one brings to the city a new face and agenda. Summer in Chicago is no exception to the rule that inhabitants take advantage of each season. Winter sees them ice skating and heading out of town for skiing at nearby hills, sporting thick layers of winter gear. In the summer, conversely, they strip to the essentials and try to handle the city’s humidity, which makes 80 degrees seem like 100.

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Chicago’s summer might be stifling at times, but tell yourself that it’s only sweat, and once back in that Chicago hostel, you’ll be rinsed clean and prepped for another day of events. And what kinds of events are we talking about here? There are all sorts of things to do in the summertime. As winter takes up half the year, locals are keen on organizing things while the weather permits shorts and T-shirts.

One of the best things you can do is check out the Taste of Chicago. Not only do you get a huge sampling of Chicago restaurants that put their fare in booths on the grounds at Grant Park, but you’re also graced with the sounds of music that come from the amphitheater, and the concert is all free. Expect big names, because the organizers always come through in flying colors.

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Another big event that takes place in Grant Park is Lollapalooza. It was once a traveling music festival, but now it’s a destination festival at its city of origin, which happens to be Chicago. Three big stages and a host of smaller ones will be pleasingly crowded with fellow festival-goers who are trying to catch a concert of some of the top names in the country. Lollapalooza is not a camping-out festival, so make sure to book your Chicago hotel early.

Street fairs happen in the neighborhoods in the summertime, and if fate hooks you up with a block party or two you will have not only a good Chicagoan experience, but a good American one as well. Custer’s Last Stand is a prime street fair that takes place on the north side, but your options will be many no matter which summer month you decide to visit the city.

Summer is the best time to see Chicago’s Navy Pier. It’s always open, but seeing it at night is pleasantest in the summer. Go on a ride around the Ferris wheel to get views of the city lit at night. Navy Pier is full of attractions; it was once the grandest pier in the world, built for the World’s Fair back in the beginning of the 20th century.

There are many things to do and see in Chicago, and if you prefer to experience cities when their inhabitants make the most of their open spaces and street life potential, then summer is the best time for your visit.

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