Latest Insights & Travel Guides

Earlier than you’d think. That’s the short answer. The longer one depends on what you’re booking, since an O’Hare pickup

With Halloween falling on a Saturday this year, Lakeview is getting ready to see Halsted Street packed with every costume

On marathon weekend, Chicago turns into one huge street festival, and the traffic pays the price. The 48th Bank of

The flight lands. Now what? Past baggage claim you’ve got three ways into the city: a taxi, Uber or Lyft,

Night of 1,000 Jack-o’-Lanterns Chicago 2026 is back at the Chicago Botanic Garden. Picture a path lit entirely by hand-carved

Twelve years running, and Arts in the Dark is coming back bigger than it’s ever been. State Street had it

Thirty-nine years. That’s how long the Lincoln Square Ravenswood Apple Fest has been giving people a reason to spend a

Looking for Chicago’s big autumn wine weekend? Lincoln Park Wine Fest 2026, one of Chicago’s fall wine festivals, is back

Twenty-nine seasons into MLS now, and Chicago Fire FC is deep into a 2026 campaign that’s brought the earliest home