Chicago does not need our help. Condé Nast Traveler’s readers have named it the best big city in the country for nine years running, and we have spent enough time in and around it to know the ranking is earned. We also know something the awards leave out: this is a warm-weather city. It is at its best from May through October, and best of all in summer. Go in February, and you will wonder what people see in it. Go in July, and you will understand.

The famous Chicago

The architecture is the best in America, and the way to see it is from the river, on a boat, with someone pointing out what you are looking at. The lakefront runs eighteen miles, with beaches and a path the whole way. The Art Institute would anchor a trip to any city. Millennium Park has the bean-shaped sculpture everyone photographs and a free summer concert series under Gehry’s band shell. The food long ago outgrew the deep-dish joke. You could fill a week this way and leave happy.

A city of neighborhoods

Chicago is a city of neighborhoods, seventy-seven of them by the official count, each with its own food and its own idea of itself. In summer, they come outside. From May into September, on nearly every weekend, a neighborhood closes a few blocks, sets up stages and food stalls, and throws a street festival. There are dozens of them.

They all follow roughly the same script. You pay a few dollars at a rope line, or nothing at all. A stage or two, a band the neighborhood is proud of, tents of local food, a beer line, a block of vendors selling things you do not need. Mostly, it's a chance to spend an afternoon in a place where Chicagoans actually live.

The festivals

Andersonville throws Midsommarfest, a nod to its Swedish roots that has run for more than fifty years. West Town has Do Division and West Fest, both heavy on music. Wicker Park Fest leans hard on music, and the Tribune has called it the best street festival of the summer. The West Loop eats its way through Taste of Randolph. Lincoln Square keeps the German and folk traditions going at Square Roots. Pilsen’s Fiesta del Sol is one of the largest Latino festivals in the Midwest. Northalsted’s Market Days takes over the city’s gay village every August, among the country’s biggest LGBTQ+ street festivals. Roscoe Village has Retro on Roscoe. Most are free or close to it.

Planning the weekend

The lineup shifts a little every year, so plan close to your trip. Choose Chicago, the city’s tourism site, keeps a running summer guide. Do312 lists the street fests as they are announced, neighborhood by neighborhood. Time Out Chicago sorts the season into what is worth your weekend. Pick a neighborhood and give a Saturday to its festival.

If you are already coming to Chicago this summer for the Obama Center, here is how to make the most of the trip. See the museum and walk the South Side, then give the next day to a neighborhood with its streets closed and its music up. Chicago is easiest to love from the middle of one of those blocks.