We Asked Locals The Best Time To Visit Chicago. Here’s The Brutal Truth.

If you ask a travel agent when to visit Chicago, they’ll show you a calendar of festivals.

If you ask a local when to visit, you’re going to get a weather report, a warning about traffic, and a lecture on proper layering.

We recently asked our 60k Facebook followers a simple question: “When is the best time to visit Chicago?”

The answers ranged from helpful to hilarious (“Whenever I’m hungry,” says Greg Phillips). But after sifting through hundreds of comments from real residents, a clear consensus emerged.

Here is the no-nonsense guide to visiting the Windy City, according to the people who actually live here.

The Undisputed Winner: “Sweater Weather” (Sept & Oct)

If there is one thing our followers agree on, it’s that autumn in Chicago is undefeated.

While summer gets all the marketing budget, September and October are the “Goldilocks” months.

As follower Steve Orr put it perfectly: “Fall, when the tourists have gone home.”

Why locals love it: The humidity breaks, the mosquitoes vanish, and you get that crisp air that makes walking the lakefront enjoyable rather than a sweat-fest.

The Vibe: As Brian Romano noted, the sweet spot is “Late September/Early October.” The patios are still open, but you aren’t fighting for a table.

The Insider Event: Keep an eye out for Open House Chicago (usually mid-October). It’s a weekend where the city unlocks doors to skyscrapers and historic buildings usually closed to the public.

The Runner Up: “Da Beginning of Summer” (May & June)

Chicago comes out of hibernation in late May and June. The energy is electric because everyone is just so relieved winter is over.

As follower Elvert J. Waters phrased it in peak Chicago dialect: “Da beginning of summer.”

The Sweet Spot: Jay Jacobs suggests the window is “Between Memorial Day and Halloween,” but most locals warned against late July and August unless you love extreme humidity.

The Neighborhood Vibe: Follower Joel Levee shouted out the Old Town Art Fair in June, which offers a classic neighborhood feel without the downtown chaos.

The Warning: If you come in July or August, be prepared to sweat. The humidity is real, and the tourist crowds at Navy Pier hit their peak.

The “Spring Trap” (March & April)

A word of caution from the locals: Do not assume April means “Spring.”

The Reality: As one follower bluntly put it, “We barely have a Spring.”

The Gamble: March and April are notoriously unpredictable. It could be 60 degrees and sunny, or it could be 35 degrees and raining sideways. If you visit during this time, pack for winter and hope for summer.

The Winter Debate: Cheap vs. Freezing

Here is where the locals split. Most will tell you to stay far away during January and February. As Jim Bettis warned: “Never, but if you do, get a very good vest just in case.”

However, there is a secret upside to the brutal cold.

The “Secret” Season: If you are on a budget, February is unmatched. Hotels are cheap, and the museums are empty.

The Valentine’s Strategy: David Chapo Dillon offered a hilarious (and practical) take on visiting in mid-February: “It’s so icy cold, you’ll have sex with your lover just to stay warm.”

The Holiday Window: If you can handle the chill, December is magical. The Christkindlmarket (Christmas market) and ZooLights are staples. Just don’t expect to feel your toes.

Dates To Avoid (Unless You Have To Be Here)

Chicago hosts massive events that take over the downtown area.

If you aren’t coming specifically for these events, do not book your trip during them. Hotel prices skyrocket and traffic becomes a parking lot.

The Chicago Marathon: Usually Columbus Day weekend (early October). While it falls during the “best weather” window, hotels sell out months in advance.

Lollapalooza: Late July / Early August. It takes over Grant Park and makes the Loop a nightmare.

St. Patrick’s Day Weekend: Specifically the Saturday before the actual holiday. The river dyeing is cool to see once, but the city turns into an amateur hour drinking fest. If that’s not your vibe, stay away.

Essential “Locals Only” Tips

The “Lake Effect”: When packing, remember it is always colder by the lake. It might be t-shirt weather in Wicker Park, but you’ll need a hoodie if you walk along the water.

The Chinatown Hack: Don’t just take an Uber to Chinatown—take the Water Taxi. It’s cheap, offers the best skyline views, and drops you right at the restaurants.

Get Out of Downtown: The Loop is for work and tourists. The real Chicago happens in the neighborhoods. Go to Pilsen for Mexican food, Andersonville for antique shops, or Lincoln Square for German beer.

The “Chicago Handshake”: If you drink, pop into a corner tavern and order this. It’s an Old Style beer and a shot of Malört. It tastes like gasoline and regret, but it’s a rite of passage.

The Verdict

According to the locals who know best: Book a flight for late September.

But if you end up here in February? Grab a coat, brave the wind, and enjoy having the Art Institute to yourself.