Millennium Park in Chicago is fine. The Bean is fine. But every visitor spends their first afternoon there, and then every visitor leaves thinking that is what Chicago parks feel like. Chicago parks do not feel like Millennium Park. Chicago parks feel like Palmer Square in Logan Square, and I would take a visitor there before I took them downtown.
Palmer Square is an oval-shaped little park with a jogging path, dog owners, families with strollers, and coffee shops within a block in every direction. It is entirely un-Instagrammable, which is why almost no visitors go. But the neighbourhood around it is where a lot of Chicagoans in their 30s actually live, and walking around it for an afternoon tells you more about the city than a whole day at the Art Institute.
The move: take the Blue Line to Logan Square. Walk to Sportsman’s Club or Lost Lot for a drink. Get pizza at Lula Cafe or breakfast at Longman & Eagle. Sit in Palmer Square with a coffee from Gaslight for an hour. You will understand Chicago as a place people love, not as a skyline you photograph. That distinction is the whole game with any city worth visiting.